Skip to main content
SpringerLink
Log in

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

  • Chapter
  • First Online:
The Chemistry of Benzotriazole Derivatives

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 43))

  • 1141 Accesses

Abstract

Application of benzotriazole methodology for the preparation of nitrogen-containing heterocyclic compounds is summarized in this review. The characteristic advantages of benzotriazole are first briefly considered followed by an overview of its use in the synthesis of heterocycles organized by the ring size. Finally, the use of benzotriazole in the synthesis of bicyclic systems is showcased in only selected examples.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Chin YW, Balunas MJ, Chai HB, Kinghorn AD (2006) AAPS J 8(2):239–253

    Article  Google Scholar 

  2. Lamberth C, Dinges J (eds) (2012) Bioactive heterocyclic compound classes: agrochemicals. Wiley-VCH, New York

    Google Scholar 

  3. Shui L, Han N, Sun Y, Liu W et al (2002) SAE Technical Paper 1:2801

    Google Scholar 

  4. Kusama H, Kurashige M, Arakawa H (2005) J Photochem Photobio A Chem 169(2):169–176

    Article  CAS  Google Scholar 

  5. Katritzky AR, Lan X (1994) Chem Soc Rev 23:363–373

    Article  CAS  Google Scholar 

  6. Katritzky AR, Lan X, Yang JZ, Denisko OV (1998) Chem Rev 98:409–548

    Article  CAS  Google Scholar 

  7. Katritzky AR, Tala SR, Singh S (2006) Synthesis 19:3231–3237

    Article  CAS  Google Scholar 

  8. Katritzky AR, Lan X, Lam JN (1991) Chem Ber 124(8):1809–1817

    Article  CAS  Google Scholar 

  9. Galli C, Gentili P, Lanzalunga O, Franco G, Sapienza L, Moro PA (2004) Chem Comm 20:2356–2357

    Article  Google Scholar 

  10. Katritzky AR, Fali CN, Li J (1997) J Org Chem 62(12):4148–4154

    Article  CAS  Google Scholar 

  11. Botuha C, Chemla F, Ferreira F, Pérez-Luna A (2011) In: Majumdar KC, Chattopadhyay SK (eds) Heterocycles in natural product synthesis. Wiley-VCH, New York, pp 1–39

    Chapter  Google Scholar 

  12. Lowden PAS (2006) In: Yudin AK (ed) Aziridines and epoxides in organic synthesis. Wiley-VCH, New York, pp 399–442

    Chapter  Google Scholar 

  13. McCoull W, Davis FA (2000) Synthesis 10:1347–1365

    Article  Google Scholar 

  14. Tanner D (1994) Angew Chem Int Ed 33(6):599–619

    Article  Google Scholar 

  15. Kim CO, Cho SJ, Park JW (2003) J Colloid Interface Sci 260(2):374–378

    Article  CAS  Google Scholar 

  16. Goethals EJ, Van de Velde M, Eckhaut G, Bouquet G (2009) In: ACS symposium series, pp 219–229

    Google Scholar 

  17. Katritzky AR, Jiang J, Urogdi L (1990) Synthesis 7:565–567

    Article  Google Scholar 

  18. Burckhalter JH, Stephens VC, Hall LAR (1952) J Am Chem Soc 74:3868–3870

    Article  CAS  Google Scholar 

  19. Katritzky AR, Rachwal S, Caster KC, Mahni F, Law KW, Rubio O (1987) J Chem Soc Perkin Trans I 781–789

    Google Scholar 

  20. Katritzky AR, Jiang J, Urogdi L (1989) Tetrahedron Lett 30(25):3303–3306

    Article  CAS  Google Scholar 

  21. Katritzky AR, Yao J, Bao W, Qi M, Steel PJ (1999) J Org Chem 64:346–350

    Article  CAS  Google Scholar 

  22. Katritzky AR, Li J, Malhotra N (1992) Liebigs Ann Chem 8:843–853

    Article  Google Scholar 

  23. Katritzky AR, Wu J, Kuzmierkiewicz W, Rachwal S (1994) Liebigs Ann Chem 1:1–5

    Article  Google Scholar 

  24. Katritzky AR, Wu J, Kuzmierkiewicz W, Rachwal S, Balasubramanian M, Steel PJ (1994) Liebigs Ann Chem 1:7–12

    Article  Google Scholar 

  25. Padwa A, Woolhouse AD (1984) In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry, vol 7. Elsevier, Amsterdam, Netherlands, pp 47–93

    Google Scholar 

  26. Nair V (1983) In: Hassner A (ed) Chemistry of heterocyclic compounds, vol 42. Wiley-VCH, New York, pp 215–332

    Chapter  Google Scholar 

  27. Stapley EO, Hendlin D, Jackson M, Miller AK, Hernandez S, Mata JM (1971) J Antibiot 24(1):42–47

    Article  CAS  Google Scholar 

  28. Miller TW, Tristram EW, Wolf FJ (1971) J Antibiot 24(1):48–50

    Article  CAS  Google Scholar 

  29. Molinski TF, Ireland CM (1988) J Org Chem 53:2103–2105

    Article  CAS  Google Scholar 

  30. Salomon CE, Williams DH, Faulkner DJ (1995) J Nat Prod 58:1463–1466

    Article  CAS  Google Scholar 

  31. Osborn HMI, Sweeney J (1997) Tetrahedron Asym 8(11):1693–1715

    Article  CAS  Google Scholar 

  32. Verstappen MMH, Ariaans GJA, Zwanenburg B (1996) J Am Chem Soc 118(35):8491–8492

    Article  CAS  Google Scholar 

  33. Palacios F, Ochoa de Retana AM, Gil JI, Ezpeleta JM (2000) J Org Chem 65(10):3213–3217

    Article  CAS  Google Scholar 

  34. Kafarski P, Lejczak B (1991) Phos Sulf Silicon Related Elem 63:193–215

    Article  CAS  Google Scholar 

  35. Katritzky AR, Zhang S, Fang Y (2000) Org Lett 2(24):3789–3791

    Article  CAS  Google Scholar 

  36. Katritzky AR, Wu J (1994) Synthesis 6:597–601

    Article  Google Scholar 

  37. Katritzky AR, Wang M, Wilkerson CR, Yang H (2003) J Org Chem 68(23):9105–9108

    Article  CAS  Google Scholar 

  38. Filler R, Kobayashi Y, Yagupolskii LM (1993) Organofluorine compounds in medicinal chemistry and biomedical applications. Elsevier

    Google Scholar 

  39. Kukhar′ VP, Soloshonok VA (1993) Fluorine-containing amino acids: synthesis and properties. Wiley-VCH, Amsterdam, Netherlands

    Google Scholar 

  40. Cheguillaume A, Lacroix S, Marchand-Brynaert J (2003) Tetrahedron Lett 44(11):2375–2377

    Article  CAS  Google Scholar 

  41. Katritzky AR, Rachwal S, Rachwal B (1987) J Chem Soc Perkin Trans 1:799–804

    Article  Google Scholar 

  42. Lacroix S, Cheguillaume A, Gérard S, Marchand-Brynaert J (2003) Synthesis 16:2483–2486

    Google Scholar 

  43. Ganem B (1996) Acc Chem Res 29(7):340–347

    Article  CAS  Google Scholar 

  44. Bachi MD, Melman A (1997) J Org Chem 62(6):1896–1898

    Article  CAS  Google Scholar 

  45. Mukai C, Sugimoto Y, Miyazawa K, Yamaguchi S, Hanaoka M (1998) J Org Chem 63(18):6281–6287

    Article  CAS  Google Scholar 

  46. Falb E, Bechor Y, Nudelman A, Hassner A, Albeck A, Gottlieb HE (1999) J Org Chem 64(2):498–506

    Article  CAS  Google Scholar 

  47. Macdonald SJF, Clarke GDE, Dowle MD, Harrison LA, Hodgson ST, Inglis GGA, Johnson MR, Shah P, Upton RJ, Walls SB (1999) J Org Chem 64(14):5166–5175

    Article  CAS  Google Scholar 

  48. Lovell PJ, Bromidge SM, Dabbs S, Duckworth DM, Forbes IT, Jennings AJ, King FD, Middlemiss DN, Rahman SK, Saunders DV, Collin LL, Hagan JJ, Riley GJ, Thomas DR (2000) J Med Chem 43(3):342–345

    Article  CAS  Google Scholar 

  49. Geneste H, Hesse M (1998) Tetrahedron 54(50):15199–15214

    Article  CAS  Google Scholar 

  50. Katritzky AR, Luo Z, Fang Y (2000) Tetrahedron Lett 41(49):9691–9693

    Article  CAS  Google Scholar 

  51. Gawley RE, Barolli G, Madan S, Saverin M, O’Connor S (2004) Tetrahedron Lett 45(8):1759–1761

    Article  CAS  Google Scholar 

  52. Katritzky AR, Cui XL, Yang B, Steel PJ (1999) J Org Chem 64(6):1979–1985

    Article  CAS  Google Scholar 

  53. Katritzky AR, Pilarski B, Urogdi L (1990) J Chem Soc Perkin Trans 1:541–547

    Article  Google Scholar 

  54. Katritzky AR, Fang Y, Qi M, Feng D (1998) Heterocycles 48(12):2535–2541

    Article  CAS  Google Scholar 

  55. Hirai Y, Terada T, Hagiwara A, Yamazaki T (1988) Chem Pharm Bull 36(4):1343–1350

    Article  CAS  Google Scholar 

  56. Brands KMJ, Meekel AAP, Pandit UK (1991) Tetrahedron 47(11):2005–2026

    Article  CAS  Google Scholar 

  57. Aurrecoechea JM, Fernández-Acebes A (1996) Synlett 1:39–42

    Article  Google Scholar 

  58. Aurrecoechea JM, Fernández A, Gorgojo JM, Saornil C (1999) Tetrahedron 55(23):7345–7362

    Article  CAS  Google Scholar 

  59. Bustos F, Gorgojo JM, Suero R, Aurrecoechea JM (2002) Tetrahedron 58(34):6837–6842

    Article  CAS  Google Scholar 

  60. Katritzky AR, Pilarski B, Urogdi L (1989) Org Prep Proc Int 21(2):135–139

    Article  CAS  Google Scholar 

  61. Padwa A, Chen YY, Chiacchio U, Dent W (1985) Tetrahedron 41(17):3529–3535

    Article  CAS  Google Scholar 

  62. Padwa A, Chen YY, Dent W, Nimmesgern H (1985) J Org Chem 50(21):4006–4014

    Article  CAS  Google Scholar 

  63. Noll JE, Speier JL, Daubert BF (1951) J Am Chem Soc 73(8):3867–3871

    Article  CAS  Google Scholar 

  64. Katritzky AR, Köditz J, Lang H (1994) Tetrahedron 50(44):12571–12578

    Article  CAS  Google Scholar 

  65. Katritzky AR, Yao J, Yang B (1999) J Org Chem 64(16):6066–6070

    Article  CAS  Google Scholar 

  66. Harrison T (1995) Contemp Org Synth 2:209–224

    Article  CAS  Google Scholar 

  67. Lin NH, Carrera JM Jr, Anderson DJ (1994) J Med Chem 37(21):3542–3553

    Article  CAS  Google Scholar 

  68. Shih NY, Lupo AT Jr, Aslanian R, Orlando S, Piwinski JJ, Green MJ, Ganguly AK, Clark MA, Tozzi S (1995) J Med Chem 38(10):1593–1599

    Article  CAS  Google Scholar 

  69. Elliott RL, Kopecka H, Lin NH, He Y, Garvey DS (1995) Synthesis 7:772–774

    Article  Google Scholar 

  70. Castelhano AL, Krantz A (1984) J Am Chem Soc 106(6):1877–1879

    Article  CAS  Google Scholar 

  71. Hiemstra H, Fortgens HP, Speckamp WN (1984) Tetrahedron Lett 25(29):3115–3118

    Article  CAS  Google Scholar 

  72. Huang PQ, Wang SL, Ye JL, Ruan YP, Huang YQ, Zheng H, Gao JX (1998) Tetrahedron 54(41):12547–12560

    Article  CAS  Google Scholar 

  73. Baenziger M, McGarrity JF, Meul T (1993) J Org Chem 58(15):4010–4012

    Article  CAS  Google Scholar 

  74. Wei ZY, Knaus EE (1993) Synlett 4:295–296

    Article  Google Scholar 

  75. Katritzky AR, Szajda M, Lam JN (1993) Heterocyclic Chem 30:1261–1265

    Article  CAS  Google Scholar 

  76. Katritzky AR, Mehta S, He HY, Cui X (2000) J Org Chem 65(14):4364–4369

    Article  CAS  Google Scholar 

  77. Katritzky AR, Angrish P, Todadze E, Ghiviriga I (2007) Bioorg Med Chem Lett 17(21):6000–6002

    Article  CAS  Google Scholar 

  78. Katritzky AR, Zhao X, Hitchings GJ (1991) Synthesis 9:703–708

    Article  Google Scholar 

  79. Katritzky AR, Hitchings GJ, Zhao X (1991) Synthesis 10:863–867

    Article  Google Scholar 

  80. Katritzky AR, Verin SV (1995) J Het Chem 32(1):323–328

    Article  CAS  Google Scholar 

  81. Trofimov BA (1990) Adv Het Chem 51:177–301

    CAS  Google Scholar 

  82. Estévez V, Villacampa M, Menéndez JC (2014) Chem Soc Rev 43:4633–4657

    Article  CAS  Google Scholar 

  83. Kaiser DG, Glenn EM (1972) J Pharm Sci 61(12):1908–1911

    Article  CAS  Google Scholar 

  84. Demir AS, Akhmedov IM, Sesenoglu O (2002) Tetrahedron 58(49):9793–9799

    Article  CAS  Google Scholar 

  85. Meshram HM, Prasad BRV, Kumar DA (2010) Tetrahedton Lett 51(27):3477–3480

    Article  CAS  Google Scholar 

  86. Davis FA, Bowen KA, Xu H, Velvadapu V (2008) Tetrahedron 64(19):4174–4182

    Article  CAS  Google Scholar 

  87. Reisser M, Maas G (2004) J Org Chem 69(15):4913–4924

    Article  CAS  Google Scholar 

  88. Mathew P, Asokan CV (2006) Tetrahedron 62(8):1708–1716

    Article  CAS  Google Scholar 

  89. Sundberg RJ (1984) In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry. Elsevier, pp 313–376

    Google Scholar 

  90. Niziurski-Mann RE, Cava MP (1992) Heterocycles 34(10):2003–2027

    Article  CAS  Google Scholar 

  91. Katritzky AR, Li J, Gordeev MF (1994) Synthesis 1:93–96

    Article  Google Scholar 

  92. Katritzky AR, Rachwal S (1992) Pol J Chem 66:1653

    CAS  Google Scholar 

  93. Katritzky AR, Chang HX, Verin SV (1995) Tetrahedron Lett 36(3):343–346

    Article  CAS  Google Scholar 

  94. Katritzky AR, Wu H, Xie L, Rachwal S, Rachwal B, Jiang J, Zhang G, Lang H (1995) Synthesis 10:1315–1323

    Article  Google Scholar 

  95. Katritzky AR, Zhang L, Yao J, Denisko OV (2000) J Org Chem 65(23):8074–8076

    Article  CAS  Google Scholar 

  96. Katritzky AR, Drewniak M, Lue P (1988) J Org Chem 53(25):5854–5856

    Article  CAS  Google Scholar 

  97. Katritzky AR, Drewniak M (1988) Tetrahedron Lett 29(15):1755–1758

    Article  CAS  Google Scholar 

  98. Katritzky AR, Zhu L, Lang H, Denisko O, Wang Z (1995) Tetrahedron 51(48):13271–13276

    Article  CAS  Google Scholar 

  99. Katritzky AR, Yao G, Lan X, Zhao X (1993) J Org Chem 58(8):2086–2093

    Article  CAS  Google Scholar 

  100. Katritzky AR, Denisko O, Lang H (1995) Tetrahedron 51(32):8703–8710

    Article  CAS  Google Scholar 

  101. Katritzky AR, Huang TB, Voronkov MV, Wang M, Kolb H (2000) J Org Chem 65(25):8819–8821

    Article  CAS  Google Scholar 

  102. Katritzky AR, Jiang J, Harris PA (1990) Heterocycles 31(12):2187–2194

    Article  CAS  Google Scholar 

  103. Katritzky AR, Jiang J, Harris PA (1991) Can J Chem 69(7):1153–1155

    Article  CAS  Google Scholar 

  104. Katritzky AR, Jiang J, Greenhill JV (1993) J Org Chem 58(8):1987–1988

    Google Scholar 

  105. Katritzky AR, Sutharchanadevi M, Urogdi L (1990) J Chem Soc Perkin Trans 1:1847–1851

    Article  Google Scholar 

  106. Katritzky AR, Cheng D, Musgrave RP (1997) Heterocycles 44(1):67–70

    Article  CAS  Google Scholar 

  107. Katritzky AR, Wang X, Denisenko A (2001) J Org Chem 66(8):2850–2853

    Article  CAS  Google Scholar 

  108. Katritzky AR, Gordeev MF, Greenhill JV, Steel PJ (1992) J Chem Soc Perkin Trans 1:1111–1117

    Article  Google Scholar 

  109. Katritzky AR, Wang Z, Li J, Levell JR (1997) J Het Chem 34(4):1379–1381

    Article  CAS  Google Scholar 

  110. Boger DL, Corbett WL (1993) J Org Chem 58(8):2068–2074

    Article  CAS  Google Scholar 

  111. Katritzky AR, Zhang S, Wang M, Kolb HC, Steel PJ (2002) J Het Chem 39(4):759–765

    Article  CAS  Google Scholar 

  112. Gupton JT, Krolikowski DA, Yu RH, Riesinger SW, Sikorski JA (1990) J Org Chem 55(15):4735–4740

    Article  CAS  Google Scholar 

  113. Angus RO Jr, Bryce MR, Keshavarz-K M, Wudl F (1988) Synthesis 9:746–748

    Article  Google Scholar 

  114. Gupton JT, Hicks FA, Smith SQ, Main AD, Petrich SA, Wilkinson DR, Sikorski JA, Katritzky AR (1993) Tetrahedron 49(45):10205–10218

    Article  CAS  Google Scholar 

  115. Ahn JH, Kim JA, Kim HM, Kwon HM, Huh SC, Rhee SD, Kim KR, Yang SD, Park SD, Lee JM, Kim SS, Cheon HG (2005) Bioorg Med Chem Lett 15(5):1337–1340

    Article  CAS  Google Scholar 

  116. Elguero J (1984) In: Katritzky AR, Rees CW (eds) Comp Het Chem 5:167–303

    Google Scholar 

  117. Katritzky AR, Qiu G, Yang B (1997) J Org Chem 62(23):8210–8214

    Article  CAS  Google Scholar 

  118. Ashton WT, Hutchins SM, Greenlee WJ, Doss GA, Chang RSL, Lotti VJ, Faust KA, Chen TB, Zingaro GJ (1993) J Med Chem 36(23):3595–3605

    Article  CAS  Google Scholar 

  119. Flynn DL, Belliotti TR, Boctor AM, Connor DT, Kostlan CR, Nies DE, Ortwine DF, Schrier DJ, Sircar JC (1991) J Med Chem 34(2):518–525

    Article  CAS  Google Scholar 

  120. Huang YR, Katzenellenbogen JA (2000) Org Lett 2(18):2833–2836

    Article  CAS  Google Scholar 

  121. Katritzky AR, Cheng D, Leeming P, Ghiviriga I, Hartshorn CM, Steel PJ (1996) J Het Chem 33(6):1935–1941

    Article  CAS  Google Scholar 

  122. Katritzky AR, Denisenko A, Denisenko SN, Arend M (2000) J Het Chem 37(5):1309–1314

    Article  CAS  Google Scholar 

  123. Katritzky AR, Henderson SA, Yang B (1998) J Het Chem 35(5):1123–1159

    Article  CAS  Google Scholar 

  124. Al-Saleh B, Abdel-Khalik MM, Darwich E, Salah OAM, Elnagdi MH (2002) Heteroatom Chem 13(2):141–145

    Article  CAS  Google Scholar 

  125. Al-Omran F, El-Khair AA (2004) J Het Chem 41(3):327–333

    Article  CAS  Google Scholar 

  126. Petrich SA, Main AD, Jaeger R, Smith SQ, Hicks FA, Gupton JT, Sikorski JA, Katritzky AR, Castle L (1994) Heterocycles 39(2):623–637

    Article  CAS  Google Scholar 

  127. Katritzky AR, Vakulenko AV, Akue-Gedu R, Gromova AV, Witek R, Rogers JW (2007) Arkivoc I:9–21

    Google Scholar 

  128. Katritzky AR, Wang M, Zhang S, Voronkov MV, Steel PJ (2001) J Org Chem 66(20):6787–6791

    Article  CAS  Google Scholar 

  129. Smith JRL, Sadd JS (1975) J Chem Soc Perkin Trans 1:1181–1184

    Article  Google Scholar 

  130. Katritzky AR, Lan X, Zhang Z (1993) J Het Chem 30(2):381–387

    Article  CAS  Google Scholar 

  131. Katritzky AR, Fali CN, Oniciu DC (1995) Tetrahedron 51(4):1069–1076

    Article  CAS  Google Scholar 

  132. Kuehne ME, Weaver SJ, Franz P (1964) J Org Chem 29(6):1582–1586

    Article  CAS  Google Scholar 

  133. Katritzky AR, Musgrave RR, Breytenbach JC (1996) J Het Chem 33(6):1637–1646

    Article  CAS  Google Scholar 

  134. Kim T, Kim K, Park YJ (2002) Eur J Org Chem 3:493–502

    Article  Google Scholar 

  135. Sharma V, Crankshaw CL, Piwnica-Worms D (1996) J Med Chem 39(18):3483–3490

    Article  CAS  Google Scholar 

  136. Sage CR, Michelitsch MD, Stout TJ, Biermann D, Nissen R, Finer-Moore J, Stroud RM (1998) Biochemistry 37(39):13893–13901

    Article  CAS  Google Scholar 

  137. Olmos G, Ribera J, García-Sevilla JA (1996) Eur J Pharm 310(1):273–276

    Article  CAS  Google Scholar 

  138. Fong JC, Benamour K, Szymonski B, Thomasson F, Morand JM, Cussac M (2000) Chem Pharm Bull 48(5):729–733

    Article  Google Scholar 

  139. Szinai SS, Crank G, Harding DRK (1970) J Med Chem 13(6):1212–1215

    Article  CAS  Google Scholar 

  140. Szinai SS, Crank G, Harding DRK (1970) J Med Chem 13(6):1215–1217

    Article  CAS  Google Scholar 

  141. Katritzky AR, Suzuki K, He HY (2002) J Org Chem 67(9):3109–3114

    Article  CAS  Google Scholar 

  142. Katritzky AR, Xu YJ, He HY, Steel PJ (2001) J Chem Soc Perkin Trans 1:1767–1770

    Article  CAS  Google Scholar 

  143. Malawska B (2005) Curr Top Med Chem 5(1):69–85

    Article  CAS  Google Scholar 

  144. Fiallo MML, Kozlowski H, Garnier-Suillerot A (2001) Eur J Pharm Sci 12(4):487–494

    Article  CAS  Google Scholar 

  145. Gregoriou M, Noble MEN, Watson KA, Garman EF, Johnson LN, Krulle TM, De La Fuetene C, Fleet GWJ, Oikonomakos NG (1998) Protein Sci 7(4):915–927

    Article  CAS  Google Scholar 

  146. Wu S, Lee S, Beak P (1996) J Am Chem Soc 118(4):715–721

    Article  CAS  Google Scholar 

  147. Katritzky AR, Luo Z, Fang Y, Steel PJ (2001) J Org Chem 66(8):2858–2861

    Article  CAS  Google Scholar 

  148. Katritzky AR, Fali CN, Li J, Ager DJ, Prakash I (1997) Synth Commun 27(9):1623–1630

    Article  CAS  Google Scholar 

  149. Butula I, Jadrijević-Mladar Takač M (2000) Croat Chem Acta 73(2):569–574

    CAS  Google Scholar 

  150. Kalčić I, Zovko M, Jadrijević-Mladar Takač M, Zorc B, Butula I (2003) Croat Chem Acta 76(3):217–228

    Google Scholar 

  151. Rajic Z, Zorc B, Raic-Malic S, Ester K, Kralj M, Pavelic K, Balzarini J, De Clercq E, Mintas M (2006) Molecules 11(11):837–848

    Article  CAS  Google Scholar 

  152. Opačić N, Barbarić M, Zorc B, Cetina M, Nagl A, Frković D, Kralj M, Pavelić K, Balzarini J, Andrei G, Snoeck R, De Clercq E, Raić-Malić S, Mintas M (2005) J Med Chem 48(2):475–482

    Article  CAS  Google Scholar 

  153. Ujjinamatada RK, Baier A, Borowski P, Hosmane RS (2007) Bioorg Med Chem Lett 17(8):2285–2288

    Article  CAS  Google Scholar 

  154. Shingalapur RV, Hosamani KM, Keri RS (2009) Eur J Med Chem 44(10):4244–4248

    Article  CAS  Google Scholar 

  155. Sharma D, Narasimhan B, Kumar P, Judge V, Narang R, De Clercq E, Balzarini J (2009) Eur J Med Chem 44(6):2347–2353

    Article  CAS  Google Scholar 

  156. Olender D, Żwawiak J, Lukianchuk V, Lesyk R, Kropacz A, Fojutowski A, Zaprutko L (2009) Eur J Med Chem 44(2):645–652

    Article  CAS  Google Scholar 

  157. Congiu C, Cocco MT, Onnis V (2008) Bioorg Med Chem Lett 18(3):989–993

    Article  CAS  Google Scholar 

  158. Katritzky AR, Wrobel L, Savage GD (1990) J Chem Res Synop 1990:330

    Google Scholar 

  159. Sanghvi YS, Bhattacharya BK, Kini GD, Matsumoto SS, Larson SB, Jolley WB, Robins RK, Revankar GR (1990) J Med Chem 33(1):336–344

    Article  CAS  Google Scholar 

  160. Moltzen EK, Pedersen H, Boegesoe KP, Meier E, Frederiksen K, Sanchez C, Lemboel HL (1994) J Med Chem 37(24):4085–4099

    Article  CAS  Google Scholar 

  161. Norris P, Horton D, Levine BR (1996) Heterocycles 43(12):2643–2655

    Article  CAS  Google Scholar 

  162. Katritzky AR, Zhang Y, Singh SK, Steel PJ (2003) Arkivoc XV:47–64

    Google Scholar 

  163. Thambidurai S, Jeyasubramanian K, Ramalingam SK (1996) Polyhedron 15(22):4011–4014

    Article  CAS  Google Scholar 

  164. Katritzky AR, Rogovoy BV, Chassaing C, Vvedensky V (2000) J Org Chem 65:8080–8082

    Article  CAS  Google Scholar 

  165. Katritzky AR, Rogovoy BV, Vvedensky VY, Kovalenko K, Steel PJ, Markov VI, Forood B (2001) Synthesis 6:897–903

    Article  Google Scholar 

  166. Boojamra SG, Burow KM, Thompson LA, Ellman JA (1997) J Org Chem 62:1240–1256

    Article  CAS  Google Scholar 

  167. Makara GM, Ma Y, Margarida L (2002) Org Lett 4(10):1751–1754

    Article  CAS  Google Scholar 

  168. Katritzky AR, Vvedensky V, Cai X, Rogovoy B, Steel PJ (2002) Arkivoc VI:82–90

    Google Scholar 

  169. Herr JR (2002) Bioorg Med Chem 10(11):3379–3393

    Article  CAS  Google Scholar 

  170. Venkatraman S, Lim J, Cramer M, Gardner MF, James J, Alves K, Lingham RB, Mumford RA, Munoz B (2005) Bioorg Med Chem Lett 15(18):4053–4056

    Article  CAS  Google Scholar 

  171. Mayer J, Umkehrer M, Kalinski C, Ross G, Kolb J, Burdack C, Hiller W (2005) Tetrahedron Lett 46(43):7393–7396

    Article  CAS  Google Scholar 

  172. Patani GA, LaVoie EJ (1996) Chem Rev 96(8):3147–3176

    Article  CAS  Google Scholar 

  173. Dömling A, Beck B, Magnin-Lachaux M (2006) Tetrahedron Lett 47(25):4289–4291

    Article  CAS  Google Scholar 

  174. Katritzky AR, Cai C, Meher NK (2007) Synlett 8:1204

    Google Scholar 

  175. Katritzky AR, Belyakov SA, Lam JN, Drust HD, Karpenko DV (1994) Heterocycles 39(1):73–80

    Article  CAS  Google Scholar 

  176. Watson PS, Jiang B, Scott B (2000) Org Lett 2:3679–3681

    Article  CAS  Google Scholar 

  177. Okitsu O, Suzuki R, Kobayashi S (2001) J Org Chem 66(3):809–823

    Article  CAS  Google Scholar 

  178. O’Hagan D (2000) Nat Prod Rep 17:435–446

    Article  Google Scholar 

  179. O’Hagan D (1997) Nat Prod Res 14:637–651

    Article  Google Scholar 

  180. Katritzky AR, Fan W (1990) J Org Chem 55(10):3205–3209

    Article  CAS  Google Scholar 

  181. Veerman JJN, Klein J, Aben RWM, Scheeren HW, Kruse CG, van Maarseveen JH, Rutjes FPJT, Hiemstra H (2002) Eur J Org Chem 18:3133–3139

    Article  Google Scholar 

  182. Wand X, Dong Y, Sun J, Xu X, Li R, Hu Y (2005) J Org Chem 70(5):1897–1900

    Article  CAS  Google Scholar 

  183. Katritzky AR, Qui G, Yang B, Steel PJ (1998) J Org Chem 63(19):6699–6703

    Article  CAS  Google Scholar 

  184. Zheng JF, Jin LR, Huang PQ (2004) Org Lett 6(7):1139–1142

    Article  CAS  Google Scholar 

  185. Katritzky AR, Luo Z, Cui XL (1999) J Org Chem 64:3328–3331

    Article  CAS  Google Scholar 

  186. Katritzky AR, Luo Z, Fang Y, Feng D, Ghiviriga I (2000) J Chem Soc Perkin Trans 2:1375–1380

    Article  Google Scholar 

  187. Katritzky AR, Gupta V, Gordeev M (1993) J Het Chem 30(4):1073–1077

    Article  CAS  Google Scholar 

  188. Katritzky AR, Gordeev MF (1993) J Org Chem 58(15):4049–4053

    Article  CAS  Google Scholar 

  189. Katritzky AR, Shcherbakova IV (1996) J Het Chem 33(6):2031–2036

    Article  CAS  Google Scholar 

  190. Alnajjar AA, Abdelkhalik MM, Al-Enezi A, Elnagdi MH (2009) Molecules 14(1):68–77

    Article  CAS  Google Scholar 

  191. Al-Saleh B, El-Apasery MA, Abdelkhalik MM, Elnagdi MH (2003) J Het Chem 40(1):171–175

    Article  CAS  Google Scholar 

  192. Katritzky AR, Belyakov SA, Sorochinsky AE, Henderson SA, Chen J (1997) J Org Chem 62(18):6210–6214

    Article  CAS  Google Scholar 

  193. Basak S, Ho YH, Tsai EW, Rajeshwar K (1989) Chem Commun 54:462–464

    Article  Google Scholar 

  194. Katritzky AR (1980) Tetrahedron 36(6):679–699

    Article  CAS  Google Scholar 

  195. Katritzky AR, Kuzmierkiewicz W, Rachwal B, Rachwal S, Thomson J (1987) J Chem Soc Perkin Trans 1:811–817

    Article  Google Scholar 

  196. Katritzky AR, Mazurkiewicz R, Stevens CV, Gordeev MF (1994) J Org Chem 59(10):2740–2742

    Article  CAS  Google Scholar 

  197. Katritzky AR, Denisenko A, Arend M (1999) J Org Chem 64(16):6076–6079

    Article  CAS  Google Scholar 

  198. Katritzky AR, Ashraf AAAF, Tymoshenko DO, Samy AE (1999) Synthesis 12:2114–2118

    Article  Google Scholar 

  199. Heinisch G, Kopelent-Frank H (1992) Prog Med Chem 29:141–183

    Article  CAS  Google Scholar 

  200. Heinisch G, Frank H (1990) Prog Med Chem 27:1–49

    Article  CAS  Google Scholar 

  201. Katritzky AR, Pleynet DPM, Yang B, Yao J (1998) Synthesis 11:1627–1631

    Article  Google Scholar 

  202. Al-Omran F, Al-Awadl N, Yousef O, Elnagdi MH (2000) J Het Chem 37:167–170

    Article  CAS  Google Scholar 

  203. Al-Mousawi S, Elassar A, El-Apasery MA (2006) Phosphorus, sulfur, silicon and the related elements. 181:1755–1771

    Google Scholar 

  204. Drandarov K, Guggisberg A, Hesse M (1999) Helv Chem Acta 82:229–237

    Article  CAS  Google Scholar 

  205. Siddiqui, AQ, Merson-Davies L, Cullis PM (1999) J Chem Soc Perkin Trans I 3243–3252

    Google Scholar 

  206. Horvath D (1997) J Med Chem 40:2412–2423

    Google Scholar 

  207. Grandos R, Alverez M, Vails N, Salas M (1983) J Med Chem 20:1271–1275

    Google Scholar 

  208. Katritzky AR, Singh SK, He H (2002) J Org Chem 67:3115–3117

    Article  CAS  Google Scholar 

  209. Katritzky AR, Toader D, Jiang J (1995) Org Prep Proc Int 27:179–184

    Article  CAS  Google Scholar 

  210. Abdel-Fattah AAA (2003) Synthesis 15:2358–2363

    Google Scholar 

  211. Zapol’skii VA, Potkin VI, Nechai NI, Kaberdin RV, Pevzner MS (1997) Russian J Org Chem 33:1461–1468

    Google Scholar 

  212. Zapol’skii VA, Namyslo JC, Altug C, Gjikaj M, Kaufmann DE (2008) Synthesis 304–311

    Google Scholar 

  213. Katritzky AR, Wang Z, Lang H (1996) Het Commun 2:109–115

    CAS  Google Scholar 

  214. Steuber CP, Krischer J, Holbrook T, Camitta B, Land V, Sexauer C, Mahoney D, Weinstein H (1996) J Clin Oncol 14:1521–1525

    CAS  Google Scholar 

  215. Momparler RM, Bovenzi V (2000) J Cell Physiol 183:145–154

    Google Scholar 

  216. Sacchi S, Kantarjian HM, O’Brien S, Cortes J, Rios MB, Giles FJ, Beran M, Koller CA, Keating MJ, Talpaz M (1999) Cancer 86:2632–2641

    Article  CAS  Google Scholar 

  217. Katritzky AR, Rogovoy BV, Vvedensky VY, Herbert N, Forood B (2001) J Org Chem 66:6797–6799

    Article  CAS  Google Scholar 

  218. Katritzky AR, Qiu G, He H, Yang B (2000) J Org Chem 65:3683–3689

    Article  CAS  Google Scholar 

  219. Katritzky AR, He H, Wang J (2002) J Org Chem 67:4951–4956

    Article  CAS  Google Scholar 

  220. Al-Mousawi SM, El-Apasery MA (2009) Molecules 14:2976–2984

    Article  CAS  Google Scholar 

  221. Katritzky AR, Levell JR, Li J (1996) Tetrahedron Lett 37:5641–5644

    Article  CAS  Google Scholar 

  222. Katritzky AR, Watson CH, Dega-Szafran Z, Eyler JR (1990) J Am Chem Soc 112:2471–2478

    Article  CAS  Google Scholar 

  223. Katritzky AR, Qiu G, Yang B, He H (1999) J Org Chem 64:7618–7621

    Article  CAS  Google Scholar 

  224. Katritzky AR, Asian D, Shcherbakova IV, Chen J, Belyakov SA (1996) J Het Chem 33:1107–1114

    Article  CAS  Google Scholar 

  225. Katritzky AR, Arend M (1998) J Org Chem 63:9989–9991

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. University of Dayton, 300 Collage Park, Dayton, OH, 45459-2357, USA

    Judit K. Beagle

Authors
  1. Judit K. Beagle
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Judit K. Beagle .

Editor information

Editors and Affiliations

  1. Center for Integrated Technology and Organic Synthesis - CiTOS, Department of Chemistry, University of Liège, Liège, Belgium

    Jean-Christophe M. Monbaliu

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Beagle, J.K. (2015). Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles. In: Monbaliu, JC. (eds) The Chemistry of Benzotriazole Derivatives. Topics in Heterocyclic Chemistry, vol 43. Springer, Cham. https://doi.org/10.1007/7081_2015_178

Download citation

Publish with us

Policies and ethics

Search

Navigation