Skip to main content
SpringerLink
Log in

One-pot, Simple, and Convenient Synthesis of 2-Thioxo-2,3-dihydroquinazolin-4(1H)-ones

  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Summary.

A simple and convenient method for the synthesis of diverse 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones was developed as one-pot reaction of anthranilic acid esters, primary amines, and bis(benzotriazolyl)methanethione in presence of the amidine base DBU.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • a) Karel W, Jii G, Hynek D, Jioi K, Lenka K, Vera K, Jarmila K (2001) Farmaco 56: 803; b) Zaidi NB, Rao RP, Sharma B (1981) Acta Ciencia Indica Chem 7: 63; c) Thangadurai SA, Kumar BRA, Ravi TK, Rajesh R, Rajasekaran S, Siddiqui AA, Alagarsamy V (2004) Ind J Het Chem 14: 183; d) Aagarsamy V, Giridhar R, Yadav MR, Revathi R, Ruckmani K, De CE (2006) Ind J Pharma Sci 68: 532; e) Sawhney SN, Tower RK, Singh SP, Prakash O, Prakash I (1980) Ind J Chem 19B: 415; f) Martin TA, Wheller AG, Majewski RF, Corrigan JR (1964) J Med Chem 7: 812

    Google Scholar 

  • a) Dienei JB, Dowalo F, Hoeven HV, Bender P, Love B (1973) J Med Chem 16: 633; b) Alagarsamy V, Pathak US (2007) Bio Med Chem 15: 3457; c) Garcia JD, Somanathan R, Rivero IA, Aguirre G, Hellberg LH (2000) Synthetic Comm 30: 2707; d) Alagarsamy V, Venkatesaperumal R, Vijayakumar S, Angayarkanni T, Pounammal P, Senthilganesh S, Kandeeban S (2004) Pharmazie 57: 306; e) Alagarsamy V, Giridhar R, Yadav MR (2006) J Pharm Pharmaco 58: 1249; f) Alagarsamy V, Giridhar R, Yadav MR (2005) Bio Pharm Bull 28: 1531; g) Alagarsamy V, Giridhar R, Yadav MR (2005) Bio Med Chem Lett 15: 3316; h) Alagarsamy V, Yadav MR, Giridhar R (2006) Arzneimittel Forschung 56: 834; i) Alagarsamy V, Giridhar R, Yadav MR (2005) Bio Med Chem Lett 15: 1877

  • a) Chandrasekhar V, Rao AR, Reddy VM (1986) Ind Drugs 3: b) Naithani PK, Palit G, Srivastava VK, Shankar K (1989) Ind J Chem 28B: 745; c) Dempcy RO, Skibo EB (1993) Bio Med Chem Lett 1: 39; d) Jen HM, Jiau HL, Chu KS, Bastow XY, Kenneth B, Hamel NY, Lee E, Hsiung K (2000) J Med Chem 43: 4479; e) Donghi M, Ferrara M, Koch U, Narjes F, Ontoria O, Jesus M, Summa V (2007) PCT Int Appl 56; f) Spencer K, Dennison H, Matthews N, Barnes M, Chana S (2005) PCT Int Appl 55; g) Alagarsamy V, Revathi R, Meena S, Ramaseshu KV, Rajasekaran S, Clercq ED (2004) Ind J Pharm Sci 66: 459; h) Hennequin LF, Boyle FT, Wardleworth JM, Marsham PR, Kimbell R, Juckman AL (1996) J Med Chem 39: 9; i) Marsham PR, Hughes LR, Jackman AL, Hayter AJ, Oldfield J, Wardleworth JM, Bishop JAM, O’Connor BM, Calvertt AH (1991) J Med Chem 34: 1594

    Google Scholar 

  • a) Alagarsamy V, Solomon VR, Dhanabal (2007) Bio Med Chem 15: 235; b) Alagarsamy V, Solomon VR, Meena R, Ramseshu KV (2005) Bio Pharm Bull 28: 1091; c) Alagarsamy V, Murugesan S (2007) Chem Pharm Bull 55: 76; d) Ravishankar CH, Rao AD, Rao AB, Reddy VM, Sattur PB (1984) Curr Sci 53: 1069; e) Alagarsamy V, Shankar D, Murugan M, Siddiqui AA, Rajesh R (2007) Archiv der Pharm 340: 41; f) Alagarsamy V, Murugananthan G, Venkateshperumal R (2003) Bio Pharm Bull 26: 1711; g) Hori M, Lemura R, Hara H, Ozaki A, Sukamoto T, Ohtaka H (1990) Chem Pharm Bull 38: 681; h) Helby E, Aly AG, Wahab A, Hemeda M (2003) Acta Pharmceutica 53: 127

  • a) For reviews see: Mhaske SB, Argade NP (2007) Tetrahedron 62: 1; b) Koepfly JB, Mead JF, Brockman JA (1947) J Am Chem Soc 69: 1837; c) Ablondi F, Gordon S, Morton J, Williams JH (1952) J Org Chem 17: 14; d) Kobayashi S, Ueno M, Suzuki R, Ishitani H (1999) Tetrahedron Lett 40: 2175; e) Jang CS, Fu FY, Wang CY, Huang KC, Lu G, Thou TC (1946) Science 103: 59

  • a) Lakhan R, Singh OP (1985) Arch Pharm Weinbeim Ger 318: 228; b) Kavalek J, Kotyk M, El BS, Sterba V (1981) Chem Comm 46: 246; c) Dave GR, Mewada GS, Amin GC (1962) Acta Chim Acad Sci 34: 101; d) Niementowski (1895) J Prakt Chem 51: 564; e) Connolly DJ, Guiry PJ (2001) Synlett 11: 1707; f) Mayoral J, Melendez E, Merchan F, Sanchez J (1981) Synthesis 12: 962; g) Garin J, Melendez E, Merchan FL, Tejero T, Villarroya E (1983) Synthesis 5: 406; h) Lakhan R, Srivastava M (1993) Proc Ind Ac Sc 105: 11; i) Banerjee RK, Lakhan R, Shukla BN (1998) J Ind Chem Soc 75: 52; j) El-H, Gamal A, Abdel M, Mohamed FZ, Tarek MM (2002) Ind J Chem 41B: 1519; k) Michman M, Patai S, Wiesel Y (1978) Org Prep Proc Int 10: 13; l) Wagner G, Rothe L (1968) Zeitschrift Chem 8: 377; m) Adharvana M, Shobha D, Mukkanti K (2006) Catalysis Comm 7: 787

  • a) George T, Rao MK, Tahilramani R (1987) Ind J Chem 26B: 1127; b) Taylor EC, Ravindranathan RV (1962) J Org Chem 27: 2622; c) Bhattacharya B (1929) J Ind Chem Soc 6: 279; d) Mhaske SB, Argade NP (2004) J Org Chem 69: 4563; e) Connoly DJ, Cusack D, Sullivan TP, Guiry PJ (2005) Tetrahedron 61: 10153; f) Bogert S (1905) J Am Chem Soc 27: 1327; g) Mehta HJ, Patel SR (1971) Ind J Chem 9: 109; h) Sun Q, Zhou X, Kyle DJ (2001) Tetrahedron Lett 42: 4119; i) Liu KC, Hsu WC (1993) Zhonghua Yaoxue Zazhi 45: 53; j) Veerachamy A, Solomon VR, Meena R, Ramseshu KV (2005) Biol Pharm Bull 28: 1091

  • a) Roy AD, Subramanian A, Roy R (2006) J Org Chem 71: 382; b) Azizian J, Mehrdad M, Jadidi K, Sarrafi Y (2000) Tetrahedron Lett 41: 5265; c) El-Deen IM, El-Desuky S (1992) J Serb Chem Soc 57: 719; d) Reddy CK, Reddy PSN, Ratnam CV (1987) Ind J Chem 26B: 882; e) Kappe T, Steiger W, Ziegler E (1967) Monatsh Chem 98: 214; f) Azizian J, Mohammadi AA, Karimi AR (2003) Syn Comm 33: 415; g) Takeuchi H, Haguvara S, Eguchi S (1989) Tetrahedron 45: 6375; h) Takeuchi H, Haguvara S, Eguchi S (1991) J Org Chem 56: 1535; i) Ghorab MM, El-Sayed BS, Saker HM, Abd R, Mahmoud M (2006) Arzneimittel Forschung 56: 665; j) Alexandre VI, Sergiy MK, Oleksandr GD (2003) J Comb Chem 5: 775

  • a) Makino S, Nakanishi E, Tsuji T (2001) Tetrahedron Lett 42: 1749; b) Makino S, Suzuki N, Nakanishi E, Tsuji T (2000) Tetrahedron Lett 41: 8333; c) Kesarwani AP, Srivastava GK, Rastogi SK, Kundu B (2002) Tetrahedron Lett 43: 5579; d) Mayer JM, Lewis GS, Curtis MJ (1997) Tetrahedron Lett 38: 8445; e) Villalgordo JM, Orbrencht D, Chucholowsky A (1998) Synlett 1405; f) Yang RY, Kaplan A (2000) Tetrahedron Lett 41: 7005; g) Makino S, Suzuki N, Nakanishi E, Suji T (2000) Synlett 11: 1670; i) Makino S, Suzuki N, Nakanishi E, Tsuji T (2001) Synlett 3: 333

  • a) For reviews on benzotriazole, see: Katritzky AR, Lan X, Yang JZ, Denisko OV (1998) Chem Rev 98: 409; b) Katritzky AR, Kavita M, Singh SK, Meher NK (2005) Tetrahedron 61: 2555; c) Katritzky AR, Ledoux S, Witek RM, Nair SK (2004) J Org Chem 69: 2976; d) Katritzky AR, Singh SK, Bobrov S (2004) J Org Chem 69: 9313

  • VK Tiwari A Singh HA Hussain BB Mishra VJ Tripathi (2007) Monatsh Chem 138 653 Occurrence Handle10.1007/s00706-007-0659-5 Occurrence Handle1:CAS:528:DC%2BD2sXmsFWqtb8%3D

    Article  CAS  Google Scholar 

  • a) Tiwari VK, Tripathi RP (2002) Ind J Chem 41B: 1681; b) Tewari N, Mishra RC, Tiwari VK, Tripathi RP (2002) Synlett 11: 1779; c) Mishra RC, Tewari N, Arora K, Ahmad R, Tripathi RP, Tiwari VK, Walter RD, Srivatava AK (2003) Comb Chem High Thr Scr 6: 36; d) Tewari N, Tiwari VK, Mishra RC, Tripathi RP, Srivastava AK, Ahmad R, Srivastava R, Srivastava BS (2003) Bio Org Med Chem 11: 2911

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Banaras Hindu University, Varanasi, India

    Vinod K. Tiwari, Hakkim A. Hussain, Bhuwan B. Mishra & Archana Singh

  2. Institute of Biomedical Science, Bundelkhand University, Jhansi, India

    Desh D. Singh

Authors
  1. Vinod K. Tiwari
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Desh D. Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hakkim A. Hussain
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Bhuwan B. Mishra
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Archana Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vinod K. Tiwari.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tiwari, V., Singh, D., Hussain, H. et al. One-pot, Simple, and Convenient Synthesis of 2-Thioxo-2,3-dihydroquinazolin-4(1H)-ones. Monatsh. Chem. 139, 43–48 (2008). https://doi.org/10.1007/s00706-007-0747-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-007-0747-6

Search

Navigation