Three-component synthesis of new γ-butyrolactones

Document Type : Original Article

Author

payame Noor university

Abstract

In this research, γ –butyrolactones were prepared using a green, mild, effective and simple method through multi-component synthesis of pyrazole carbaldehyde or indole-3-carbaldehyde, ethylpyruvate and N-bromosuccinimide. The mechanistical pathway for this reaction includes bromination reaction, condensation reaction followed by intra-molecular cyclization. This methodology is completely new and the products were synthesized in short reaction times and high yields. This protocole has advantages as simple method, aqeous media, and reduced environmentally consequences. All of the synthesized compounds were characterized by melting points, infra-red spectroscopy, nuclear magnetic resonance (1H NMR, 13C NMR) and elemental analysis. The novelty of this protocole combined with the novelty of the synthesized compounds is the other highlights of this procedure.

Keywords

References

[1] a) S. Huang, L. Yang, W. Xiao, C. Lei, J. Liu, Y. Lu, Z. Weng, L. Li, R. Li, J. Yu, Q. Zheng and H. Sun, Chem. Eur. J. 13 (2007) 4816; b) H. N. Kamel, D. Ferreira, L. F. Garcia-Fernandez and M. Slattery, J. Nat. Prod. 70 (2007) 1223; c) Y. Wang, C. Tang, P. Dien and Y. Ye, J. Nat. Prod. 70 (2007) 1356; d) T. Hu, I. W. Burton, A. D. Cembella, J. M. Curtis, M. A. Quilliam, J. A. Walter and J. L. C. Wright, J. Nat. Prod. 64 (2001) 308; e) T. Seki, M. Satake, L. MacKenzie, H. F. Kaspar and T. Yasumoto, Tetrahedron Lett. 36 (1995) 7093 ; f) J. S. Roach, P. LeBlanc, N. I. Lewis, R. Munday, M. A. Quilliam and S.  L. MacKinnon, J. Nat. Prod. 72 (2007) 1237 -1240; g) B. M. Fraga, Nat. Prod. Rep. 19 (2002) 650; h) C. E. Cook, L. P. Whichard, B. Turner, M. E. Wall and G. H. Egley, Science 154 (1966) 1189; i) R. A. Fernandes, P. H. Patil and A. K. Chowdhury,  Asian J. Org. Chem. 3 (2014) 58; j) A. de Fa´tima, L. K. Kohn, M. Aparecid, Anto, J. E. de Carvalho and R. A. Pilli, Bioorg. Med. Chem. 13 (2005) 2927; k) S. B. Buck, C. Hardouin, S. Ichikawa, D. R. Soenen, C. –M. Gauss, I. Hwang, M. R. Swingle, K. M. Bonness, R. E. Honkanen and D. L. Boger, J. Am. Chem. Soc. 125 (2003) 15694. l) F. Doragi,M. Javaherian, J. of Applied chemistry, 13 (1397) 189.
[2] C. W. Cho and M. J. Krische, Angew. Chem. 116 (2004) 6857.
[3] C. Shu, M. –Q. Liu, Y. –Z. Sun and L. –W. Ye, Org. Lett. 14 (2012) 4958.
[4] T. Dohi, N. Takenaga, A. Goto, A. Maruyama and Y. Kita, Org. Lett. 9 (2007) 3129.
[5] S. K. Murphy and V. M. Dong, J. Am. Chem. Soc. 135 (2013) 5553.
[6] C. –G. Yang, N. W. Reich, Z. Shi and C. He, Org. Lett. 7 (2005) 4553.
[7] P. Y. Toullec, E. Genin, S. Antoniotti, J. –P. Genêt and V. Michelet, Synlett (2008) 707.
[8] L. Huang, H. Jiang, C. Qi and X. Liu, J. Am. Chem. Soc. 132 (2010) 17652.
[9] S. Bonollo, A. Z. Ahmady, C. Petrucci, A. Marocchi, F. Pizzo and L. Vaccaro, Org. Lett. 16 (2014) 5721.
[10] B. Beck, M. Magnin-Lachaux, E. Herdtweck and A. Domling, Org. Lett. 3 (2001) 2875.
[11] P. I. Dalko and L. Moisan, Angew. Chem. Int. Ed. 43 (2004) 5138.
[12] K. Surendra, N. S. Krishnaveni, V. P. Kumar, R. Sridhar and K. R. Rao, Tetrahedron Lett. 46 (2005) 4581.
[13] B. Karimi, H. Hazarkhani and J. Maleki, Synthesis (2005) 279.
[14] S. K. Talluri and A. Sudalai, Org. Lett. 7 (2005) 855.
[15] N. S. Krishnaveni, K. Surendra and K. R. Rao, Adv. Synth. Catal. (2004) 346.
[16] R. Rajagopal, D. V. Jarikote, R. J. Lahoti, D. Thomas and K. V. Srinivasan, Tetrahedron Lett. 44 (2003) 1815.
[17] A. Podgorsek, S. Stavber, M. Zupan and J. Iskra, Tetrahedron Lett. 47 (2006) 1097.
[18] I. Pravst, M. Zupan and S. Stavbre, Tetrahedron  Lett. 47 (2006) 4707.
[19] J. Wu, W. Sun, X. Sun and H. –G. Xia, Green Chem. 8 (2006) 365.
[20] C. –W. Kuo, S. V. More and C. –F. Yao, Tetrahedron Lett. 47 (2006) 8523.
[21] (a) C. J. Li, Chem. Rev. 105 (2005) 3095. (b) M. O. Simon and C. J. Li,  Chem. Soc. Rev. 41 (2012) 1415.
[22] L. Zare, N. O. Mahmoodi, A. Yahyazadeh and M. Mamaghani, Synth. Commun. 41 (2011) 2323.
[23] L. Zare, N. O. Mahmoodi, A. Yahyazadeh and M. Nikpassand, Ultrason. Sonochem. 19 (2012) 740.
[24] L. Zare Fekri, M. Nikpassand and K. Hassanpour, Curr. Org. Syn. 12 (2015) 76.
[25] L. Zare Fekri and M. Nikpassand, Russ. J. Gen. Chem. 84 (2014) 1825.
[26] L. Z. Fekri and R. Maleki, J. Hetero. Chem. 54 (2017) 1167.
[27] L. Z. Fekri, M. Nikpassand and R. Maleki, J. Mol. Liq. 222 (2016) 77.
[28] M. Nikpassand and L. Zare Fekri, J. of Applied chemistry, 14 (1398) 323
Applied Chemistry Today
Volume 15, Issue 56
September 2020
Pages 257-266

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