Three component one-pot synthesis of 4H-benzo-[b]-pyran derivatives using [(diacetoxyiodo)benzene] (DIB) as a hypervalent iodine catalyst

Document Type: Original Research Article

Authors

Department of Chemistry, Padmashri Vikhe Patil College of Arts, Science and Commerce, Pravaranagar, 413713 Maharashtra, India

Abstract

The three components one pot synthesis of 2-amino-4H-benzo-[b] -pyran derivatives were obtained in good to excellent yields within short reaction time by condensing dimedone, aldehydes and malanonitrile or ethylcyanoacetate using a catalytic amount of (diacetoxyiodo)benzene as hypervalent iodine in aqueous ethanol under reflux conditions have been discussed. This aqua mediated Knoevenagel-cyclocondensation of various aromatic and hetero-aromatic aldehydes along with the aldehydes like aryl-sulphonyloxybenzaldehyde, aryl-carbonyloxybenzaldehyde also leads to the product under the same reaction conditions. High yields, shorter reaction times, one pot condensation, operational simplicity, easy work-up, purification of products by non-chromatographic methods are some additional features of the present protocol.

Graphical Abstract

Three component one-pot synthesis of 4H-benzo-[b]-pyran derivatives using [(diacetoxyiodo)benzene] (DIB) as a hypervalent iodine catalyst

Keywords

Main Subjects


[1] P.A. Wender, S.L. Handy, D.L. Wright, Chem. Ind. (London), 1997, 765-769.

[2] P.T. Anastas, T.C. Williamson, In Green Chemistry, Designing Chemistry for the Environment, Eds. American Chemical Society, Washington, D, C, 1996, 1-17.

[3] P.A. Grieco, Organic Synthesis in Water,

Thomson Science, Glasgow, Scotland, 1998,

1-80, 250-261.

[4] L. Bonsignoren, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem., 1993, 28, 517-520.

[5] W.O. Foye Principi di Chemico Farmaceutica; Piccin: Padora, Italy, 1991, 416.

[6] L.L. Andreani, E. Lapi, Bull. Chim. Farm., 1960, 99, 583-586.

[7] Y.L. Zhang, B.Z. Chen, K.Q. Zheng, M.L. Xu, L.Z. Zhang, X.H. Lei, Yao Xue XueBao,  1982, 17, 17-22.

[8] E.C. Witte, P. Neubert, A. Roesch, Ger. Offen. De., 1986, 3427985; Chem. Abstr., 1986, 104, 224915f.

[9] N.J. Thumar, M.P. Patel, ARKIVOC 2009, xii, 363-380.

[10] C.S. Konkoy, D.B. Fick, S.X. Cai, N.C. Lan, J.F. W. Keana, PCT Int. Appl,. 2000, WO0075123; Chem. Abstr., 2000, 134, 2931a.

[11] S. Hatakeyama, N. Ochi, H. Numata, S. Takano, J. Chem. Soc., Chem. Commun. 1988, 1202-1204.

[12] C. N. O’Callaghan, T. B. H. McMurry, J. Chem. Res. (S), 1995, 214-218.

[13] D. Arnesto, W. M. Horspool, N. Martin, A. Ramos, C. Seaone, J. Org. Chem., 1989, 54, 3069-3072.

[14] T. Ponpandian, S. Muthusubramanian Synth. Commun. 2014, 44, 868-874.

[15] B.C. Ranu, S. Banerjee, S. Roy, Ind. J. Chem,. 47B 2008, 1108-1112.

[16] S.J. Tu, H. Wang, J.Q. Feng, A. Tang, J. Feng, Synth. Commun., 2001, 31, 2663-2666.

[17] K. Mogilaiah, A.V. Chandra, N.Srivani, K. Shiv Kumar, Ind. J. Chem. 2013, 52B, 306-308.

[18] I. Devi, P.J. Bhuyn, Tet. Lett. 2004, 45, 8625-8627.

[19] N.M. Abd El-Rahman, A.A. El-Kateb, M.F. Mady, Synth. Commun., 2007, 37, 3961-3970.

[20] J.T. Li, W.Z. Xu, L.C. Yang, T.S. Li, Synth. Commun., 2004, 34, 4565-4571.

[21]A. Hasaninejad, N. Jafarpour, M. Mohammadnejad, E-J. Chem., 2012, 9, 2000-2005.

[22] D. Tahmasssebi, J.A. Bryson, S.I. Binz, Synth. Commun., 2011, 41, 2701-2711.

[23] S. Gao, C.S. Tsai, C. Tseng, C.F. Yao, Tetrahedron, 2008, 64, 9143-9149.

[24] Z.G. Zeng, L.Y. Wang, Y. Cao, Y.P. Luo, Res. Chem. Intermed. 2012, 38, 1751-1760.

[25] T. Jin, A. Wang, F. Shi, L.Han, L. Liu T. Li, ARKIVOC, 2006, xiv, 78-86.

[26] L. Zhao, Y. Li, L. Chen, B. Zhou, Chin J. Org. Chem., 2010, 30, 124-127.

[27] M.M. Khodaei, K. Bahrami, A. Farrokhi, Synth Commun., 2010, 40, 1492-

1499.

[28] N.M. Hilmy Elnagdi, N. S. Al-Hokbany, molecules, 2012, 17, 4300-4312.

[29] L. Wang, J. Shao, H. Tian, Y. Wang, B. Liu, J. Fluorine Chem., 2006, 127, 97-100.

[30] R. Bhosale, C. Magar, K. Solanke, S. Mane, S. Choudhary, R. Pawar, Synth. Commun., 2007, 37, 4353-4357.

[31] S. Khaksar, A. Rouhollahpour, S.M. Talesh, J. Fluorine Chem., 2012, 141, 11-15.

[32] D.P. More, K.A. Undale, B.P. Dongare, U. V. Desai, Catal. Lett., 2009, 132, 104-108.

[33] G. Brahmachari, B. Banerjee, ACS Sustainable Chem. Eng., 2014, 2, 411-422.

[34] D. Azarifar, S. Khatami, R. Nejat-Yami J. Chem. Sci., 2014, 126, 95-101.

[35] A. Rostami, B. Atashkar, H. Gholami, Catal. Commun., 2013, 37, 69-74.

[36] R. Criegee, H. Beucker, Justus Liebigs, Ann. Chem., 1939, 541, 218-238.

[37] A. Peller, S. Elgendy, Tet. Lett., 1988, 29, 677-680.

[38] A. Varvoglis, Hypervalent Iodine in Organic synthesis, Academic Press, 1997, 19-47.

[39] V.V. Zhdankin, In Hypervalent Iodine Chemistry; Wirth, T., Ed.; Spring-Verlag: New York, 2003; Chapter 4, 93-136.