A green protocol for synthesis of pyran annulated hetrocyclic systems using Na2SO4 as an efficient catalyst

الموضوعات : Iranian Journal of Catalysis

Malek Taher Maghsoodlou ¹ (Department of Chemistry, The University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran)
Amin Masoumnia ² (Department of Chemistry, The University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran)
Mir Rasul Mousavi ³ (Department of Chemistry, The University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran)
Nourollah Hazeri ⁴ (Department of Chemistry, The University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran)
Jasem Aboonajmi ⁵ (Department of Chemistry, The University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran)
Sayyed Mostafa Habibi-Khorasani ⁶ (Department of Chemistry, The University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran)
Shiva Kiaee ⁷ (Department of Chemistry, The University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran)

تاريخ الإرسال : 08 الأربعاء , ذو القعدة, 1435 تاريخ التأكيد : 11 الأربعاء , صفر, 1436 تاريخ الإصدار : 14 الإثنين , شعبان, 1436

الکلمات المفتاحية: 4-hydroxycoumarin, Pyran annulated hetrocyclic systems, Na2SO4, Green protocol, Barbituric acid,

ملخص المقالة :

Na2SO4 as an inexpensive and effective catalyst has provided a green protocol for the synthesis of tetrahydrobenzo[b]pyran, pyrano[2,3-d]pyrimidinone and dihydropyrano[3,2c]chromene derivatives from the three-component domino reaction of aromatic aldehydes and malononitrile with 4-hydroxycoumarin/ dimedone/ barbituric acid in ethanol/water as a mixture of solvent that, this mixture entirely is green solvent. Products could simply be separated from the catalyst. Using neutral and mild conditions, short reaction time, environmentally benign procedure, high to excellent yields of the products and easy work-up without using column chromatography are the advantages of this method. By virtue of these advantages, sodium sulfate can be used as catalyst in the organic transformations.

المصادر:

[1] X. Zhang, A. Amer, X. Fan, J. Balzarini, J. Neyts, E. De Clercq, M. Prichard, E. Kern, P.F. Torrence, Bioorg. Chem. 35 (2007) 221-232.
[2] C. Luo, P. Xie, R. Marmorstein, J. Med. Chem. 51 (2008) 6121-6127.
[3] X. Fan, X. Zhang, L. Zhou, K.A. Keith, M.N. Prichard, E.R. Kern, P.F. Torrence, J. Med. Chem. 49 (2006) 4052-4054.
[4] S. Gao, C.H. Tsai, C. Tseng, C.F. Yao, Tetrahedron 64 (2008) 9143-9149.
[5] J. Marco-Contelles, R. Leon, C. de los Rıos, A.G. Garcıa, M.G. Lopez, M. Villarroya, Bioorg. Med. Chem. 14 (2006) 8176-8185.
[6] P.F. Torrence, X. Fan, X. Zhang, P.M. Loiseau, Bioorg. Med. Chem. Lett. 16 (2006) 5047-5051.
[7] I. Devi, P.J. Bhuyan, Tetrahedron Lett. 45 (2004) 8625-8627.
[8] S.B. Rajesh, V.M. Chandrakant, S.S. Kuldeep, B.M. Sandeep, S.C. Sunil, P.P. Rajendra, Synth. Commun. 37 (2007) 4353-4357.
[9] X.S. Wang, D.Q. Shi, S.J. Tu, C.S. Yao, Synth. Commun. 33 (2003) 119-126.
[10] S. Abdolmohammadi, S. Balalaie, Tetrhedron Lett. 48 (2007) 3299-3303.
[11] S. Gao, C.H. Tsai, C. Tseng, C.F. Yao, Tetrahedron 64 (2008) 9143-9149.
[12] M. Seifi, H. Sheibani, Catal. Lett. 126 (2008) 275-279.
[13] R. Hekmatshor, S. Majedi, K. Bakhtiari, Catal. Commun. 9 (2008) 307-310.
[14] Y.M. Ren, C. Cai, Catal. Commun. 9 (2008) 1017-1020.
[15] M.M. Heravi, B.A. Jani, F. Derikvand, F.F. Bamoharram, H.A. Oskooie, Catal. Commun. 10 (2008) 272-275.
[16] J.M. Khurana, S. Kumar, Tetrahedron Lett. 50 (2009) 4125-4127.
[17] W.O. Sun, P. Zhang, J. Fan, S.H. Chen, Z.H. Zhang, Synth. Commun. 40 (2010) 587-594.
[18] M.M. Khodaei, K. Bahrami, A. Farrokhi, Synth. Commun. 40 (2010) 1492-1499.
[19] D. Fang, H.B. Zhang, Z.L. Liu, J. Heterocycl. Chem. 47 (2010) 63-67.
[20] S.S. Katkar, M.K. Lande, B.R. Arbad, S.T. Gaikwad, Chin. J. Chem. 29 (2011) 199-202.
[21] J. Zheng, Y.Q. Li, Scholar Res. Lib. 3 (2011) 381-388.
[22] P.P. Salvi, A.M. Mandhare, A.S. Sartape, D.K. Pawar, S.H. Han, S.S. Kolekar, C. R. Chim.  14 (2011)  878-882.
[23] M.R. Mousavi, J. Aboonajmi, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, M. Safarzaei, Lett. Org. Chem. 10 (2013) 171-177.
[24] M.T. Maghsoodlou, K. Khandan-Barani, N. Hazeri, S.M. Habibi-Khorassani, A.C. Willis, Res. Chem. Intermed. 40 (2014)779-785.
[25] F. Farhadpour, N. Hazeri, S. Salahi, P. Dastoorani, R. Doostmohammadi, M. Lashkari, M. Ghashang, M.T. Maghsoodlou, Iran. J. Catal. 4 (2014) 247-251.
[26] N. Hazeri, S. Mohamadian-Souri, M.T. Maghsoodlou, M. Lashkari, M. Ghashang, Iran. J. Catal. Corrected Proof.
[27] H.J. Wang, J. Lu, Z.H. Zhang, Monatsh. Chem. 141 (2010) 1107-1112.
[28] H.R. Shaterian, M. Arman, F. Rigi, J. Mol. Liq. 158 (2011) 145-150.
[29] J.M. Khurana, B. Nand, P. Saluja, Tetrahedron 66 (2010) 5637-5641.
[30] S. Nemouchi, R. Boulcina, B. Carboni, A. Debache, C.R. Chim. 15 (2012) 394-397.
[31] A. Mobinikhaledi, M.A.B. Fard, Acta. Chim. Slov. 57 (2010) 931-935.
[32] S. Balalaie, M. Bararjanian, M. Sheikh‐Ahmadi, S. Hekmat, P. Salehi, Synth. Commun. 37 (2010) 1097-1108.
[33] L. Fotouhi, M.M. Heravi, A. Fatehi, K. Bakhtiari, Tetrahedron Lett. 48 (2007) 5379-5381.
[34] X.Z. Lian, Y. Huang, Y.Q. Li, W.J. Zheng, Monatsh. Chem. 139 (2008) 129-131.
[35] D.M. Pore, K.A. Undale, B.B. Dongare, U.V. Desai, Catal. Lett. 132 (2009) 104-108.
[36] J.Z. Qin, J.S. Jun, L. Jun, Y.J. Ming, Chin. J. Chem. 23 (2005) 1085-1089.
[37] Y. Gao, S. Tu, T. Li, X. Zhang, S. Zhu, F. Fang, D. Shi, Synth. Commun. 34 (2006) 1295-1299.