Abstract
This chapter deals with the methods for the syntheses of 2,5-dihydro-1,2-oxaphosphole-2-oxide derivatives, and some recent results of their biological activity testing. The electrophilic addition to 1,2-alkadiene- and alkatrienephosphonate derivatives is one of the easiest and fruitful synthetic strategies for obtaining these compounds in preparative amounts.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Similar content being viewed by others
References
Kafarski P, Lejczak B (2001) Curr Med Chem 1:301
Colvin OM (1999) Curr Pharm Des 5:555
Zon G (1982) Prog Med Chem 19:205
Stec W (1982) J Organophosphorus Chem 13:145
Mader MM, Bartlett PA (1997) Chem Rev 97:1281
Kafarski P, Lejczak B (1991) Phosphorus Sulfur Silicon Relat Elem 63:193
Franz JE, Mao MK, Sikorski JA (1997) Gliphosate: a unique global herbicide. American Chemical Society, Washington, DC
Bhattacharya AK, Thyagarajan G (1981) Chem Rev 81:415
Engel R (1988) Synthesis of carbon-phosphorus bonds. CRC, Boca Raton, FL
Marianoff BE, Reitz AB (1989) Chem Rev 89:863
Pudovik AN (1989) Chemistry of organophosphorus compounds. MIR, Moskow
Motoyoshiya J (1998) Trends Org Chem 7:63
Kann N, Rein T (2003) Synthesis:579
Bricklebank N (2003) Organophosphorus Chem 33:289
Mathey F (ed) (2001) Phosphorus-carbon heterocyclic chemistry: the rise of a new domain. Pergamon, New York
Quin LD (1981) The heterocyclic chemistry of phosphorus: systems based on the phosphorus-carbon bond. Wiley, New York
Darrow JW, Drueckenhammer DG (1994) J Org Chem 59:2976
Morita I, Kunimoto K, Tsuda M, Tada SI, Kise M, Kimura K (1987) Chem Pharm Bull 35:4144
Stewart JD, Liotta LJ, Benkivic SJ (1993) Acc Chem Res 26:396
Racha S, Vargeese C, Vemishetti P, El-Subbagh H, Abushanab E, Paniza RP (1996) J Med Chem 39:1130
McReinolds MD, Dougherty JM, Hanson PR (2004) Chem Rev 104:2239
Macomber RS, Krudy GA, Seff K, Rendon-Diaz-Miron LE (1983) J Org Chem 48:1425
Christau HJ, Pirat JL, Virieux D, Monbrum J, Ciptadi C, Berko Y (2005) J Organomet Chem 690:2472
Hah J, Lee B, Lee S, Lee H (2003) Tetrahedron Lett 44:5811
Abramovitch RA, Konieczny M, Pennington W, Kanamatharaddy S, Vedachalam M (1990) J Chem Soc Chem Commun:269
Peng A-Y, Ding Y-X (2005) Org Lett 7:3299
Ma S, Yu F, Zhao J (2007) Synlett:583
Yu F, Lian X, Ma S (2007) Org Lett 9:1703
Moedritzer K, Miller RE (1982) J Org Chem 47:1530
Civunin VS, Kamay GH, Fridland ES (1966) Russ J Gen Chem 36:436
Civunin VS, Fridland ES, Zikova TV, Kamay GH (1966) Russ J Gen Chem 36:1424
Civunin VS, Kamay GH, Fridland ES (1967) USSR Patent 196822:12
Pudovik AN, Dmitrieva VK, Samitov UU, Shagidulin RR, Hairulin VK (1969) Russ J Gen Chem 2219:39
Campbell IGM, Raza SM (1971) J Chem Soc:1836
Udelevich VI, Sokolov LB, Ionin BI, Petrov AA (1980) Russ J Gen Chem 50:1419
Dmitrieva GV, Pudovik AN, Hairulin VK (1969) USSR Patent 246512:21
Hairulin VK, Dmitrieva GV, Pudovik AN (1971) Russ Chem Bull:1254
Macomber RS (1971) J Org Chem 36:2713
Macomber RS, Elder RS, Florian LR, Kennedy ER (1973) J Org Chem 38:4177
Mashida Y, Sato I (1979) J Org Chem 44:865
Beliaeva TN, Sendurev MV, Dogadina AV, Ionin BA, Petrov AA (1982) Russ J Gen Chem 52:2472
Mark V (1962) Tetrahedron Lett:281
Khusainova NG, Pudovik AN (1978) Russ Chem Rev 47:1507
Khusainova NG, Pudovik AN (1987) Russ Chem Rev 56:975
Angelov ChM (1983) Phosphorus Sulfur Silicon Relat Elem 15:177
Alabugin IV, Brel VK (1997) Russ Chem Rev 66:225
Yavari I, Hossaini Z, Sabbaghan M, Ghazanfarpour-Darjan M (2004) Tetrahedron Lett 44:2877
Landor SR (ed) (1982) The chemistry of allenes. Academic Press, London 2: 351
Schuster HF, Coppola GM (1984) Allenes in organic synthesis. Wiley, New York
Krause N, Haschmi ASK (eds) (2004) Modern allene chemistry. Wiley, Weinheim
Padwa A, Meske M, Ni Z (1995) Tetrahedron 51:89
Elsevier SJ (1995) In: Helmchen G, Hoffman RW, Mulzer J, Schaumann E (eds) Methods of organic chemistry (Houben-Weyi), E21. Thieme, Stuttgart, p 537
Braverman S, Reisman D (1977) Tetrahedron Lett:1753
Macomber RS (1977) J Am Chem Soc 99:3072
Shingu K, Hagashita S, Nakagawa M (1967) Tetrahedron Lett:4371
Jacobs TL, Macomber RS, Zunker D (1967) J Am Chem Soc 89:7001
Mulla M, Macomber RS (1989) Synth Commun 19:1997
Udelevich VI, Belahov VV, Komarov EV, Ionin BI, Petrov AA (1983) Dokl Chem 269:1377 CA 99:18881a
Belahov VV, Udelevich VI, Komarov EV, Ionin BI, Petrov AA (1983) Russ J Gen Chem 53:2139
Belahov VV, Udelevich VI, Jakovlev AA, Ionin BI (1986) Russ J Gen Chem 56:333
Belahov VV, Udelevich VI, Ionin BI (1986) Russ J Gen Chem 56:718
Belahov VV, Ionin BI (1989) Russ J Gen Chem 59:2143
Belahov VV, Ionin BI (1986) Russ J Gen Chem 56:1421
Belahov VV, Udelevich VI, Komarov EV, Ionin BI, Petrov AA (1983) Russ J Gen Chem 53:2758
Angelov ChM (1980) Russ J Gen Chem 50:2448
Macomber RS (1977) J Org Chem 48:3072
Macomber RS (1978) J Org Chem 49:1832
Angelov ChM, Ignatiev VM et al (1976) USSR Patent 550401:10
Angelov ChM, Vachkov KV, Kirilov M, Ionin BI, Vasilev GN, Petrov AA (1978) Compt Rend Bul Acad Sci 31:1589
Ignatiev VM, Angelov ChM, Ionin BI, Petrov AA (1975) Russ J Gen Chem 45:2342
Angelov ChM, Mikhailova TS, Ignatiev VM, Zaharov VI, Dogadina AV, Ionin BI, Petrov AA (1978) Russ J Gen Chem 48:1487
Mikhailova TS, Angelov ChM, Ignatiev VM, Ionin BI, Petrov AA (1979) Russ J Gen Chem 49:570
Angelov ChM, Christov VCh (1981) Compt Rend Bul Acad Sci 34:67
Angelov ChM, Christov VCh, Ionin BI (1981) Russ J Gen Chem 51:1230
Brel VK, Ionin BI, Petrov AA (1982) Russ J Gen Chem 52:816
Brel VK, Dogadina AV, Ionin BI, Petrov AA (1980) Russ J Gen Chem 50:1890
Brel VK, Ionin BI, Petrov AA (1981) Russ J Gen Chem 51:2625
Brel VK, Ionin BI, Petrov AA (1983) Russ J Gen Chem 53:234
Brel VK, Ionin BI, Petrov AA, Martinov IV (1985) Russ J Gen Chem 55:2465
Berkova GA, Shehade MA, Zaharov VI, Ionin BI, Petrov AA (1977) Russ J Gen Chem 47:957
Angelov ChM, Enchev DD, Kirilov M (1983) Russ J Gen Chem 53:1958
Enchev DD (2005) Phosphorus Sulfur Silicon Relat Elem 180:2211
Angelov ChM, Kirilov M (1980) Compt Rend Bul Acad Sci 33:937
Purdela D, Vilchanu R (1972) The chemistry of organic compounds of phosphorus. Khimia, Moskow
Angelov ChM (1982) Phosphorus Sulfur Silicon Relat Elem 37:187
Macomber RS, Kennedy ER (1976) J Org Chem 41:3191
Husainova NG, Naumova LV, Berdnikov EA, Pudovik AN (1982) Russ J Gen Chem 52:1040
Pudovik AN, Khusainova NG, Berdnikov EA (1980) Dokl Chem 250:116 CA 92:32159a
Khusainova NG, Naumova LV, Berdnikov EA, Kutyrev GA, Pudovik AN (1982) Phosphorus Sulfur Silicon Relat Elem 13:147
Khusainova NG, Berdnikov EA, Naumova LV, Pudovik AN (1983) Russ Chem Bull:1851
Angelov ChM, Vachkov KV, Kirilov M (1982) Russ J Gen Chem 52:538
Angelov ChM, Vachkov KV (1984) Phosphorus Sulfur Silicon Relat Elem 21:237
Angelov ChM, Stoianov NM, Ionin BI (1982) Russ J Gen Chem 52:178
Braverman S, Reisman D (1977) J Am Chem Soc 99:605
Mikhailova TS, Angelov ChM, Dogadina AV, Zaharov VI, Ignatiev VM, Ionin BI, Petrov AA (1977) Russ J Gen Chem 47:2701
Shehade AM, Zaharov VI, Ignatiev VM, Ionin BI, Petrov AA (1978) Russ J Gen Chem 48:55
Angelov ChM, Kirilov M, Ionin BI, Petrov AA (1979) Russ J Gen Chem 49:2225
Prudnikova OG, Brel VK, Ionin BI (1986) Russ J Gen Chem 56:764
Angelov ChM, Christov ChZh (1983) Heterocycles 20:219
Pudovik AN, Husainova NG (1967) Russ J Gen Chem 37:1889
Alabugin IV, Sereda GA, Abramkin EV, Brel VK, Zik NV, Zefirov NS (1995) Dokl Chem 345:487 CA 127:12587a
Angelov ChM, Enchev DD, Kirilov M, Jivkova TD (1984) Bulgarian Patent N 10/15.10.1984
Mikhailova TS, Zaharov VI, Ignatiev VM, Ionin BI, Petrov AA (1980) Russ J Gen Chem 50:1690
Mikhailova TS, Zaharov VI, Ignatiev VM, Ionin BI, Petrov AA (1978) Russ J Gen Chem 48:701
Enchev DD (2005) Heteroatom Chem 16:156
Angelov ChM, Stoianov NM, Kirilov M, Vasilev GN, Dimcheva ZP (1978) Bulgarian Patent 25139:8
Angelov ChM, Vachkov KV, Petrova J, Kirilov M (1982) Phosphorus Sulfur Silicon Relat Elem 14:7
Alabugin IV, Brel VK, Zefirov NS (1993) Russ J Gen Chem 63:2387
Alabugin IV, Brel VK, Chehlov AN, Zefirov NS, Stang JP (1994) Tetrahedron Lett 35:8275
Angelov ChM, Vachkov KV, Kirilov M, Ionin BI, Petrov AA (1979) Compt Rend Bul Acad Sci 32:611
Husainova NG, Berdnikov EA, Naumova LV, Pudovik AN (1984) Russ J Gen Chem 54:1425
Angelov ChM, Tancheva ChM (1985) Russ J Gen Chem 55:53
Angelov ChM, Christov ChZh (1980) Russ J Gen Chem 50:1891
Angelov ChM (1983) Heterocycles 20:791
Angelov ChM, Christov ChZh (1984) Synthesis:664
Enchev DD (1997) Phosphorus Sulfur Silicon Relat Elem 122:101
Enchev DD, Angelov ChM, Krawchik E, Skovronska A, Michalski J (1991) Phosphorus Sulfur Silicon Relat Elem 57:249
Christov VCh, Prodanov B (2002) Phosphorus Sulfur Silicon Relat Elem 177:234
Christov VCh, Prodanov B (2002) Heterocycl Commun 8:349
Christov VCh, Prodanov B (2002) Heterocycles 57:1777
Brel VK (2006) Heteroatom Chem 17:547
Brel V K (1998) Synthesis:710
Yuan J, Ruan X, Yang Y, Huang X (2007) Synlett:2871
Angelov ChM, Enchev DD (1988) Phosphorus Sulfur Silicon Relat Elem 37:125
Angelov ChM, Enchev DD (1992) Heteroatom Chem 3:651
Christov VCh, Vasilev VT, Angelov ChM (1993) Phosphorus Sulfur Silicon Relat Elem 77:185
Christov VCh, Angelov ChM (1997) Phosphorus Sulfur Silicon Relat Elem 122:227
Enchev DD, Angelov ChM (1987) Phosphorus Sulfur Silicon Relat Elem 34:163
Enchev DD (2008) Phosphorus Sulfur Silicon Relat Elem 183:2649
Enchev DD, Nikolov NG, Angelov ChM (1987) Proceedings of the IV international symposium on plant-growth regulators, Bulgaria, 365
Angelov ChM, Enchev DD (1987) Bulgarian Patent N 9/15.09.1987
Kalcheva VP, Dragoeva AP, Kalchev KN, Enchev DD (2009) Gen Mol Biol 32:389
Enchev DD unpublished data
Enchev DD (2005) Phosphorus Sulfur Silicon Relat Elem 180:2131
Enchev DD (2005) Phosphorus Sulfur Silicon Relat Elem 180:2141
Kohn KW, Hartley JA, Mattes WB (1987) Nucleic Acids Res 15:10531
Hemminki K (1985) Cancer Res 45:4237
Kwon ChH, Moon KY, Baturay N, Shirota FN (1991) J Med Chem 34:588
Vu VT, Fenselau CC, Colvin OM (1981) J Am Chem Soc 103:7362
Colvin M, Brundrett RB, Kan MNN, Jardine I, Fenselau C (1976) Cancer Res 36:1121
Rink SM, Solomon MS, Taylor MJ, Rajur SB, McLaughlin LM, Hopkins PB (1993) J Am Chem Soc 115:2551
LeRoux C, Baumeister S, Modro TM (1993) J Chem Res (S):372
Engle TW, Zon G, Egan W (1982) J Med Chem 25:1347
Baumeister S, Modro TM, Modro TA (1989) Tetrahedron Lett 30:2141
Haranath P, Anasuyamma U, Naga Raju C, Devendranath Reddy C, Suresh Reddy CJ (2005) Heteroatom Chem 42:775
Angelov ChM, Enchev DD, Kirilov M (1988) Phosphorus Sulfur Silicon 35:35
Angelov ChM, Vachkov KV (1981) Tetrahedron Lett 22:2517
Zik NV, Alabugin IV, Kutateladze AG, Keis JL, Zefiriv NS (1994) Dokl Chem 337:208 CA 123:25669a
Enchev DD, Stankolov SP (2007) Phosphorus Sulfur Silicon Relat Elem 182:1857
Angelov ChM, Christov VCh, Ionin BI (1982) Russ J Gen Chem 52:264
Angelov ChM, Christov ChZh, Mondeshka DM (1984) Phosphorus Sulfur Silicon Relat Elem 21:249
Enchev DD (2000) Phosphorus Sulfur Silicon Relat Elem 165:273
Shehade AM, Ignatiev VM, Zaharov VI, Ionin BI, Petrov AA (1977) Russ J Gen Chem 47:720
Shehade AM, Ignatiev VM, Zaharov VI, Ionin BI, Petrov AA (1979) Russ J Gen Chem 49:337
Christov VCh, Angelov ChM (1992) Phosphorus Sulfur Silicon Relat Elem 68:223
Christov VCh (1998) Phosphorus Sulfur Silicon Relat Elem 53:132
Brel VK, Dogadina AV, Ionin BI, Petrov AA (1980) Russ J Gen Chem 50:1625
Brel VK, Komarov YaV, Ionin BI, Petrov AA (1983) Russ J Gen Chem 53:66
Angelov ChM, Christov VCh (1984) Chem Scr 24:92 CA 102:9785a
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2010 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Enchev, D.D. (2010). Synthesis and Biological Activity of 2,5-Dihydro-1,2-Oxaphosphole-2-Oxide Derivatives. In: Bansal, R. (eds) Phosphorus Heterocycles II. Topics in Heterocyclic Chemistry, vol 21. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2009_4
Download citation
DOI: https://doi.org/10.1007/7081_2009_4
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-12253-8
Online ISBN: 978-3-642-12254-5
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)