Citation: Goravanahalli M. Raghavendra, Chottanahalli S. Pavan Kumar, Gejjalagere P. Suresha, Kanchugarakoppal S. Rangappa, Kempegowda Mantelingu. T3P catalyzed one pot three-component synthesis of 2,3-disubstituted 3H-quinazolin-4-ones[J]. Chinese Chemical Letters, ;2015, 26(8): 963-968. doi: 10.1016/j.cclet.2015.03.037 shu

T3P catalyzed one pot three-component synthesis of 2,3-disubstituted 3H-quinazolin-4-ones

  • Corresponding author: Kanchugarakoppal S. Rangappa,  Kempegowda Mantelingu, 
  • Received Date: 25 December 2014
    Available Online: 27 February 2015

    Fund Project: Financial support from DST-Fast track, New Delhi (No. SERB/F/ 2013-14) is gratefully acknowledged. (No. SERB/F/ 2013-14)

  • An efficient methodology for the synthesis of 2,3-disubstituted 3H-quinazolin-4-ones is described via one-pot three component reaction from anthranilic acid using T3P as catalyst. Mild reaction conditions, short reaction time, broad functional group tolerance, easy isolation of products and good yields are main advantages of this protocol.
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    1. [1]

      [1] A. Dö mling, Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev. 106 (2006) 17-89.

    2. [2]

      [2] C. Hulme, V. Gore, Multi-component reactions: emerging chemistry in drug discovery ‘From Xylocain to Crixivan’, Curr. Med. Chem. 10 (2003) 51-80.

    3. [3]

      [3] J. Zhu, Recent developments in the isonitrile-based multicomponent synthesis of heterocycles, Eur. J. Org. Chem. (2003) 1133-1144.

    4. [4]

      [4] A. Dö mling, I. Ugi, Multicomponent reactions with isocyanides, Angew. Chem. Int. Ed. 39 (2000) 3168-3210.

    5. [5]

      [5] (a) L. Weber, High-diversity combinatorial libraries, Curr. Opin. Chem. Biol. 4 (2000) 295-302; (b) A. Domling, Recent advances in isocyanide-based multicomponent chemistry, Curr. Opin. Chem. Biol. 6 (2002) 306-313.

    6. [6]

      [6] S.B. Mhaske, N.P. Argade, The chemistry of recently isolated naturally occurring quinazolinone alkaloids, Tetrahedron 62 (2006) 9787-9826.

    7. [7]

      [7] T. Onaka, A general three-step synthesis of pyrrolidino[2,1-b]quinazolone alkaloids via biogenetically patterned path, Tetrahedron Lett. 12 (1971) 4387-4390.

    8. [8]

      [8] A. Hamid, A. Elomri, A. Daich, Expedious and practical synthesis of the bioactive alkaloidsrutaecarpine, euxylophoricine A, deoxyvasicinone and their heterocyclic homologues, Tetrahedron Lett. 47 (2006) 1777-1781.

    9. [9]

      [9] J.R. Sheu, Pharmacological effects of rutaecarpine, an alkaloid isolated from evodia rutaecarpa, Cardiovasc. Drug Rev. 17 (1999) 237-245.

    10. [10]

      [10] J. Michel, Quinoline, quinazoline and acridone alkaloids, Nat. Prod. Rep. 21 (2004) 650-668.

    11. [11]

      [11] A.M. Al-Obaid, S.G. Abdel-Hamide, H.A. El-Kashef, et al., Substituted quinazolines, part 3. Synthesis, in vitro antitumor activity and molecular modeling study of certain 2-thieno-4(3H)-quinazolinone analogs, Eur. J. Med. Chem. 44 (2009) 2379-2391.

    12. [12]

      [12] A.S. El-Azab, M.A. Al-Omar, A.A. Abdel-Aziz, et al., Design, synthesis and biological evaluation of novel quinazoline derivatives as potential antitumor agents: molecular docking study, Eur. J. Med. Chem. 45 (2010) 4188-4198.

    13. [13]

      [13] J.F. Wolfe, T.L. Rathman, M.C. Sleevi, J.A. Campbell, T.D. Greenwood, Synthesis and anticonvulsant activity of some new 2-substituted 3-aryl-4(3H)-quinazolinones, J. Med. Chem. 33 (1999) 161-166.

    14. [14]

      [14] K. Terashima, H. Shimamura, A. Kawase, et al., Studies on antiulcer agents. IV: Antiulcer effects of 2-benzylthio-5,6,7,8-tetrahydro-4(3H)-quinazolinones and related compounds, Chem. Pharm. Bull. 43 (1995) 2021-2023.

    15. [15]

      [15] J.B. Koepfli, J.F. Mead, J.A. Brockman Jr., An alkaloid with high antimalarial activity from dichroa-febrifuga, J. Am. Chem. Soc. 69 (1947) 1837.

    16. [16]

      [16] S. Kobayashi, M. Ueno, R. Suzuki, H. Ishitani, Catalytic asymmetric synthesis of febrifugine and isofebrifugine, Tetrahedron Lett. 40 (1999) 2175-2178.

    17. [17]

      [17] S.L. Cao, Y.P. Feng, Y.Y. Jiang, et al., Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains, Bioorg. Med. Chem. Lett. 15 (2005) 1915-1917.

    18. [18]

      [18] M.A.G. Nagwa, H.G. Hanan, M.Y. Riham, A.E.S. Nehad, Synthesis and antitumor activity of some 2,3-disubstituted quinazolin-4(3H)-ones and 4,6-disubstituted-1,2,3,4-tetrahydroquinazolin-2H-ones, Eur. J. Med. Chem. 45 (2010) 6058-6067.

    19. [19]

      [19] C. Huang, Y. Fu, H. Fu, Y. Jiang, Y. Zhao, Highly efficient copper-catalyzed cascade synthesis of quinazoline and quinazolinone derivatives, Chem. Commun. 46 (2008) 6333-6335.

    20. [20]

      [20] J.F. Liu, J. Lee, M.A. Dalton, et al., Microwave-assisted one-pot synthesis of 2,3-disubstituted 3H-quinazolin-4-ones, Tetrahedron Lett. 46 (2005) 1241-1244.

    21. [21]

      [21] I.K. Kostakis, A. Elomri, E. Segunin, M. Iannelli, T. Besson, Rapid synthesis of 2,3-disubstituted quinazolin-4-ones enhanced by microwave-assisted decomposition of formamide, Tetrahedron Lett. 48 (2007) 6609-6613.

    22. [22]

      [22] M. Adib, E. Sheikhi, H.R. Bijanzadeh, Benzyl halides, that are first oxidized to aldehydes under mild Kornblum conditions, undergo a three-component reaction with isatoic anhydride and primary amines to produce 4(3H)-quinazolinones in excellent yields, Synlett 23 (2012) 85-88.

    23. [23]

      [23] A. Kumar, A.K. Bishnoi, Nanoparticle mediated organic synthesis (NAMO-synthesis): CuI-NP catalyzed ligand free amidation of aryl halides, RSC Adv. 4 (2014) 41631-41635.

    24. [24]

      [24] H. Wei, T. Li, Y. Zhou, L. Zhou, Q. Zeng, Copper-catalyzed domino synthesis of quinazolin-4(3H)-ones from (hetero) arylmethyl halides, bromoacetate, and cinnamyl bromide, Synthesis 45 (2013) 3349-3354.

    25. [25]

      [25] J. Zhou, L. Fu, M. Lv, et al., Copper(I) iodide catalyzed domino process to quinazolin-4(3H)-ones, Synthesis 24 (2008) 3974-3980.

    26. [26]

      [26] J. Raid, J.V. Wolfgang, S. Muhammad, A novel method for the synthesis of 4(3H)-quinazolinones, Tetrahedron Lett. 45 (2004) 3475-3476.

    27. [27]

      [27] H. Wissmann, H.J. Kleiner, New peptide synthesis, Angew. Chem. 92 (1980) 133-134.

    28. [28]

      [28] R. Escher, P. Bunning, Synthesis of N-(1-Carboxy-5-aminopentyl)dipeptides as inhibitors of angiotensin converting enzyme, Angew. Chem. Int. Ed. 25 (1986) 277-278.

    29. [29]

      [29] N. Basavaprabhu, R.S. Narendra, V.V. Lamani, Sureshbabu, T3P® (propylphosphonic anhydride) mediated conversion of carboxylic acids into acid azides and one-pot synthesis of ureidopeptides, Tetrahedron Lett. 51 (2010) 3002-3005.

    30. [30]

      [30] B.S. Patil, G.R. Vasanthakumar, V.V. Sureshbabu, Isocyanates of N α-[(9-fluorenylmethyl) oxy]carbonyl amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of urea peptidomimetics, J. Org. Chem. 68 (2003) 7274-7280.

    31. [31]

      [31] J.K. Augustine, A. Bombrun, A.B. Mandal, et al., Propylphosphonic anhydride (T3P1)-mediated one-pot rearrangement of carboxylic acids to carbamates, Synthesis 9 (2011) 1477-1483.

    32. [32]

      [32] M. Desroses, T. Koolmeister, S. Jacques, et al., A facile and efficient synthesis of tetrahydro-β-carbolines, Tetrahedron Lett. 54 (2013) 3554-3557.

    33. [33]

      [33] T.M. Basavaprabhu, N.R. Vishwanatha, V.V. Panguluri, Sureshbabu, Propanephosphonic acid anhydride (T3P®) -a benign reagent for diverse applications inclusive of large-scale synthesis, Synthesis 45 (2013) 1569-1601.

    34. [34]

      [34] G.M. Raghavendra, A.B. Ramesha, C.N. Revanna, et al., One-pot tandem approach for the synthesis of benzimidazoles and benzothiazoles from alcohols, Tetrahedron Lett. 52 (2011) 5571-5574.

    35. [35]

      [35] A.B. Ramesha, G.M. Raghavendra, K.N. Nandeesh, K.S. Rangappa, K. Mantelingu, Tandem approach for the synthesis of imidazo[1,2-a]pyridines from alcohols, Tetrahedron Lett. 54 (2013) 95-100.

    36. [36]

      [36] C.N. Revanna, G.M. Raghavendra, T.A. Jenifer Vijay, et al., Propylphosphonic anhydride-catalyzed tandem approach for biginelli reaction starting from alcohols, Chem. Lett. 43 (2014) 178-180.

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