注册 English

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

Goravanahalli M. Raghavendra ,  Chottanahalli S. Pavan Kumar ,  Gejjalagere P. Suresha ,  Kanchugarakoppal S. Rangappa ,  Kempegowda Mantelingu

downloadPDF
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

    • 通讯作者: Kanchugarakoppal S. Rangappa,
    Kempegowda Mantelingu,
  • 基金项目:

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

摘要: 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.

English

  • 

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

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

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

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

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

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

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

    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.[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] 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.[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] 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.[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] 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.[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] 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.[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] 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.[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] 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.[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] 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.[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] J. Zhou, L. Fu, M. Lv, et al., Copper(I) iodide catalyzed domino process to quinazolin-4(3H)-ones, Synthesis 24 (2008) 3974-3980.[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] J. Raid, J.V. Wolfgang, S. Muhammad, A novel method for the synthesis of 4(3H)-quinazolinones, Tetrahedron Lett. 45 (2004) 3475-3476.[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] H. Wissmann, H.J. Kleiner, New peptide synthesis, Angew. Chem. 92 (1980) 133-134.[27] H. Wissmann, H.J. Kleiner, New peptide synthesis, Angew. Chem. 92 (1980) 133-134.

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

  • 加载中
WeChat 扫一扫看文章
计量
  • PDF下载量:  0
  • 文章访问数:  1649
  • HTML全文浏览量:  117
文章相关
  • 发布日期:  2015-04-03
  • 收稿日期:  2014-12-25
  • 网络出版日期:  2015-02-27
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章

All Rights Reserved by the Chinese Chemical Society   中国化学会 版权所有 京ICP备05002797号

本系统由北京仁和汇智信息技术有限公司开发    技术支持: info@rhhz.net