Reviews

Progress in Application of L-Proline in Catalyzing the Synthesis of Heterocyclic Compounds

  • Wang Huiyuan ,
  • Li Lili ,
  • Lin Wei ,
  • Huang Zhibin ,
  • Shi Daqing
Expand
  • College of Chemistry, Chemical Engineering and Materials Science, Key Laboratory of Organic Synthesis of Jiangsu Province, Soochow University, Suzhou 215123

Received date: 2012-10-18

  Revised date: 2013-01-18

  Online published: 2013-03-15

Supported by

Project supported by the National Natural Science Foundation of China (No. 21072144).

Abstract

Heterocyclic compounds have shown many important applications in medicine, pesticide and materials. The synthetic method of heterocyclic compounds is one of the focused fields in organic synthesis. Small organic molecules like L-proline and its derivatives are readily commercially available catalyst and have been used in some important organic reactions. The applications of L-proline in catalyzing the synthesis of heterocyclic compounds in recent years are reviewed. Most mentioned synthetic methods have the advantages of mild reaction conditions, easily operation, high yields and environmentally friendly.

Cite this article

Wang Huiyuan , Li Lili , Lin Wei , Huang Zhibin , Shi Daqing . Progress in Application of L-Proline in Catalyzing the Synthesis of Heterocyclic Compounds[J]. Chinese Journal of Organic Chemistry, 2013 , 33(08) : 1616 -1627 . DOI: 10.6023/cjoc201210033

References

[1] List, B.; Lerner, R. A.; Barbas, C. F. Ⅲ J. Am. Chem. Soc. 2000, 122, 2395.
[2] List, B. Acc. Chem. Res. 2004, 37, 548.
[3] List, B.; Mukherjee, S.; Yang, J. W.; Hoffmann, S. Chem. Rev. 2007, 107, 5471.
[4] Notz, W.; Tanaka, F.; Barbas, C. F. Ⅲ. Acc. Chem. Res. 2004, 37, 580.
[5] Gewald, K. Chem. Ber. 1965, 98, 3571.
[6] Sampson, N.; Bartlett, P. J. Org. Chem. 1991, 56, 7179.
[7] Wang, T.; Huang, X. G.; Liu, J.; Li, B.; Wu, J. J.; Chen, K. X.; Zhu, W. L.; Xu, X. Y.; Zeng, B. B. Synlett 2010, 1351.
[8] Lambardino, J. G.; Wiseman, E. H. J. Med. Chem. 1974, 17, 1182.
[9] Siddiqui, S. A.; Narkhede, U. C.; Palimkar, S. S.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Tetrahedron 2005, 61, 3539.
[10] Wang, J.; Mason, R.; Derveer, D. V.; Feng, K.; Bu, X. R. J. Org. Chem. 2003, 68, 5415.
[11] Sarshar, S.; Siev, D.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 835.
[12] Shaabani, A.; Rahmati, A. J. Mol. Catal. A: Chem. 2006, 249, 246.
[13] Sangshetti, J. N.; Kokare, N. D.; Kothrkara, S. A.; Shinde, D. B. J. Chem. Sci. 2008, 120, 463.
[14] Bogevig, A.; Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
[15] Balalaie, S.; Arabanian, A. Green Chem. 2002, 2, 274.
[16] Heravi, M. M.; Derikvand, F.; Bamoharram, F. F. J. Mol. Catal. A: Chem. 2007, 263, 112
[17] Sadeghi, B.; Mirjalili, B. B. F.; Hashemi, M. M. Tetrahedron Lett. 2008, 49, 2575.
[18] Karimi, A. R.; Alimohammadi, Z.; Azizian, J.; Mohammadi, A. A.; Mohammadizadeh, M. R. Catal. Commun. 2006, 7, 728.
[19] Samai, S.; Nandi, G. C.; Singh, P.; Singh, M. S. Tetrahedron 2009, 65, 10155.
[20] Love, B.; Goodman, M. M.; Snader, K. M.; Tedeschi, R.; Macko, E. J. Med. Chem. 1974, 19, 956.
[21] Hantzsch, A. Justus Liebigs Ann. Chem. 1882, 215, 1.
[22] Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1.
[23] Stout, D. M.; Meyers, A. T. Chem. Rev. 1982, 82, 223.
[24] Sivamurugan, V.; Kumar, R. S.; Palanichamy, M.; Murugesan, V. J. Heterocycl. Chem. 2005, 42, 969.
[25] Kumar, A.; Maurya, R. A. Tetrahedron 2008, 64, 3477.
[26] Jiang, H.; Mai, R.; Cao, H.; Zhu, Q.; Liu, X. Org. Biomol. Chem. 2009, 7, 4943.
[27] Jiang, H.; Li, J.; Chen, Z. Tetrahedron 2010, 66, 9721.
[28] Shi, C. L.; Chen, H.; Li, Y.; Shi, D. Q.; Ji, M. J. Chem. Res. 2008, 534.
[29] Karade, N. N.; Budhewar, V. H.; Shinde, S. V.; Jadhav, W. N. Lett. Org. Chem. 2007, 4, 16.
[30] Kumar, A.; Maurya, R. A. Tetrahedron 2007, 63, 1946.
[31] Rajanarendar, E.; Reddy, M. N.; Raju, S. Indian J. Chem. 2011, 50B, 751.
[32] Yu, D.; Wang, Y.; Xu, P. Tetrahedron 2011, 67, 3273.
[33] Krohnke, F. Synthesis 1976, 1.
[34] Potts, K. T.; Cipullo, M. J.; Ralli, P.; Theodoridis, G. J. Am. Chem. Soc. 1981, 103, 3584.
[35] Palacios, F.; De Retana, A. M. O.; Oyarzabal, J. Tetrahedron Lett. 1996, 37, 4577.
[36] Smith, C. B.; Raston, C. L.; Sobolev, A. N. Green Chem. 2005, 7, 650.
[37] Smith, N. M.; Raston, C. L.; Smith, C. B.; Sobolev, A. N. Green Chem. 2007, 9, 1185.
[38] Mukhopadhyay, C.; Tapaswi, P. K.; Butcher, R. J. Tetrahedron Lett. 2010, 51, 1797.
[39] Srinivasan, M.; Perumal, S.; Selvaraj, S. ARKIVOC 2005, 201.
[40] Shi, C. L.; Shi, D. Q.; Kim, S. H.; Huang, Z. B.; Ji, M. Aust. J. Chem. 2008, 61, 547.
[41] McGlacken, G. P.; Fairlamb, I. J. S. Nat. Prod. Rep. 2005, 22, 369.
[42] Balalaie, S.; Ramezanpour, S.; Bararjanian, M.; Gross, J. H. Synth. Commun. 2008, 38, 1078.
[43] Nagarajan, A. S.; Reddy, B. S. Synlett 2009, 2002.
[44] Banerjee, S.; Horn, A.; Khatri, H.; Sereda, G. Tetrahedron Lett. 2011, 52, 1878.
[45] Elnagdi, N. M. H.; Al-Hokbany, N. S. Molecules 2012, 17, 4300.
[46] Balalaie, S.; Bararjanian, M.; Amani, M.; Movassagh, B. Synlett 2006, 263.
[47] Shanthi, G.; Perumal, P. T.; Rao, U.; Sehgal, P. K. Indian J. Chem. 2009, 48B, 1319.
[48] Biginelli, P. Ber. 1891, 24, 1317.
[49] Kappe, C. O. Acc. Chem. Res. 2000, 33, 879.
[50] Wang, R.; Liu, Z. Q. J. Org. Chem. 2012, 77, 3952.
[51] Yadav, J. S.; Kumar, S. P.; Kondaji, G.; Rao, R. S.; Nagaiah, K. Chem. Lett. 2004, 33, 1168.
[52] Indumathi, S.; Perumal, S.; Banerjee, D.; Yogeeswari, P. Eur. J. Med. Chem. 2009, 44, 4978.
[53] Indumathi, S.; Perumal, S.; Menendez, J. C. Tetrahedron 2011, 67, 7101.
[54] Chandrasekhar, S.; Vijeender, K.; Srdhar, C. Tetrahedron Lett. 2007, 48, 4935.
[55] Pechmann, V. H.; Duisberg, C. Chem. Ber. 1984, 117, 929.
[56] Perkin, W. H.; Henry, W. S. J. Chem. Soc. 1875, 28, 10.
[57] Jones, F.; Piermatti, O.; Pizzo, F. Heterocycles 1996, 43, 1257.
[58] Shriner, R. L. Org. React. 1942, 1, 15.
[59] Maercker, A. Org. Synth. 1934, 14, 270.
[60] Karade, N. N.; Gampawar, S. V.; Shinde, S. V.; Jadhav, W. N. Chin. J. Chem. 2007, 25, 1686.
[61] Shi, C. L.; Shi, D. Q. J. Chem. Res. 2011, 585.
[62] Junek, H.; Aigner, H. Chem. Ber. 1973, 106, 914.
[63] Guo, S. B.; Wang, S. X.; Li, J. T. Synth. Commun. 2007, 37, 2111.
[64] Mecadon, H.; Rohman, M. R.; Kharbangar, I.; Laloo, B. M.; Kharkongor, I.; Rajbangshi, M.; Myrboh, B. Tetrahedron Lett. 2011, 52, 3228.
[65] Muramulla, S.; Zhao, C. G. Tetrahedron Lett. 2011, 52, 3905.
[66] Bararjanian, M.; Balalaie, S.; Movassagh, B.; Amani, A. M. J. Iran. Chem. Soc. 2009, 6, 436.
[67] Pandey, J.; Anand, N.; Tripathi, R. P. Tetrahedron 2009, 65, 9350.
[68] Wang, X. S.; Zeng, Z. S.; Shi, D. Q.; Wei, X. Y.; Zong, Z. M. Synth. Commun. 2004, 34, 4331.
[69] Mont, N.; Teixido, J.; Borrella, J. I.; Kappe, C. O. Tetrahedron Lett. 2003, 44, 5385.
[70] Shi, D. Q.; Niu, L. H.; Shi, J. W.; Wang, X. S.; Ji, S. J. J. Heterocycl. Chem. 2007, 44, 1083.
[71] Samai, S.; Nandi, C. S.; Chowdhury, S.; Singh, M. S. Tetrahedron 2011, 67, 5935.
[72] Shi, C. L.; Chen, H.; Shi, D. Q. J. Heterocycl. Chem. 2011, 48, 351.
[73] Varala, R.; Nasreen, A.; Enugala, R.; Adapa, S. R. Tetrahedron Lett. 2007, 48, 69.
[74] Kumari, K.; Raghuvanshi, D. S.; Singh, K. N. Indian J. Chem. 2012, 51B, 860.
[75] Chebanov, V. A.; Saraev, V. E.; Kobzar, K. M.; Desenko, S. M.; Orlov, V. D.; Gura, E. A. Chem. Heterocycl. Compd. 2004, 442, 571.
[76] Shi, D. Q.; Shi, J. W.; Yao, H. Chin. J. Org. Chem. 2009, 29, 239.
[77] Wang, X. S.; Shi, D. Q.; Wang, S. H.; Tu, S. J. Chin. J. Org. Chem. 2003, 23, 1291.
[78] Zare, L.; Nikpassand, M. Chin. Chem. Lett. 2011, 22, 531.
[79] Nikpassand, M.; Zare, L.; Saberi, M. Monatsh. Chem. 2012, 143, 289.
[80] Tratrat, C.; Renault, S. G.; Husson, H. P. Org. Lett. 2002, 4, 3187.
[81] Tu, S. J.; Zhang, Y.; Zhang, J. Y.; Jiang, B.; Jia, R. H.; Zhang, J. P.; Ji, S. J. Synlett 2006, 2785.
[82] Shi, C. L.; Wang, J. X.; Chen, H.; Shi, D. Q. J. Comb. Chem. 2010, 12, 430.
[83] Shi, C. L.; Chen, H.; Shi, D. Q. J. Heterocycl. Chem. 2012, 49, 125.
[84] Abdolmohammadi, S.; Balalaie, S. Tetrahedron Lett. 2007, 48, 3299.
[85] Shi, C. L.; Shi, D. Q.; Kim, S. H.; Huang, Z. B.; Ji, S. J.; Ji, M. Tetrahedron 2008, 64, 2425.
[86] Wang, H. Y.; Li, L. L.; Lin, W.; Xu, P.; Huang, Z. B.; Shi, D. Q. Org. Lett. 2012, 14, 4598.
[87] Rajesh, S. M.; Bala, B. D.; Perumal, S.; Menendez, J. C. Green Chem. 2011, 13, 3248.
[88] Khalafi-Nezhad, A.; Sarikhani, S.; Shahidzadeh, E. S.; Panali, F. Green Chem. 2012, 14, 2876.
[89] Darvesh, S.; Darvesh, K. V.; McDonald, R. S.; Mataija, D.; Walsh, R.; Mothana, S.; Lockridge, O.; Martin, E. J. Med. Chem. 2008, 51, 4200.
[90] Kubota, K.; Kurebayashi, H.; Miyachi, H.; Tobe, M.; Onishi, M.; Isobe, Y. Bioorg. Med. Chem. Lett. 2009, 19, 2766.
[91] Bisi, A.; Meli, M.; Gobbi, S.; Rampa, A.; Tolomeo, M.; Dusonchet, L. Bioorg. Med. Chem. 2008, 16, 6474.
[92] Ma, D. W.; Geng, Q.; Zhang, H.; Jiang, Y. W. Angew. Chem., Int. Ed. 2010, 49, 1291.
[93] Redkin, R. G.; Shemchuk, L. A.; Chernykh, V. P.; Shishkin, O. V.; Shishkina, S. V. Tetrahedron 2007, 63, 11444.
[94] Shanthi, G.; Subbulakshmi, G.; Perumal, P. T. Tetrahedron 2007, 63, 2057.
[95] Mohammadi, A. A.; Dabiri, M.; Qaraat, H. Tetrahedron 2009, 65, 3804.
[96] Chandrasekhar, S.; Reddy, N. R.; Sultana, S. S.; Narsihmulu, C.; Reddy, K. V. Tetrahedron 2006, 62, 338.
[97] Li, Y. L.; Chen, H.; Shi, C. L.; Shi, D. Q.; Ji, S. J. J. Comb. Chem. 2010, 12, 231.
[98] Raghuvanshi, D. S.; Singh, K. N. J. Heterocycl. Chem. 2010, 47, 1323.
[99] Dabiri, M.; Tisseh, Z. N.; Nobahar, M.; Bazgir, A. Helv. Chim. Acta 2011, 94, 824.
[100] Khorrami, A. R.; Kiani, P.; Bazgir, A. Monatsh. Chem. 2011, 142, 287.
[101] Chandrasekhar, S.; Vijeender, K.; Reddy, K. V. Tetrahedron Lett. 2005, 46, 6991
[102] Wu, X. S.; Lin, S. Z.; Li, M. Z.; You, T. P. Synlett 2009, 1501.
Outlines

/