Clean and green synthesis of structurally diverse 4H-benzo[b]pyrans derivatives in water
Keywords:
Magnesium sulphate, 4H-Benzo[b]pyran, Dimedone, Aldehyde, Malononitrile, Water mediumAbstract
Magnesium sulphate has been reported as a cheap and readily available common desk reagent for the synthesis of highly functionalized 4H-benzo[b]pyran derivatives. The synthesis of target compounds was accomplished by one pot multicomponent reaction of aldehydes, malononitrile and dimedone or 4-hydroxycoumarin, aldehyde in under reflux temperature. The corresponding 4H-benzo[b]pyrane derivatives were obtained in good excellent yield under optimized reaction conditions. The methodology prescribed here was found to be adventitious over reported protocols in terms of generality, environment friendliness and economic viability.
References
- L.F. Tietze, G. Brasche and K. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 1996.
- L.F. Tietze, Chem. Rev. 1996, 96, 115.
- A. D’omling, I. Ugi,? Angew. Chem. Int. Ed. 2000, 39, 3168.
- J. Zhu, H. Bienaym?e,? Multicomponent Reactions, 1st Ed. 2005.
- J.E.G. Kemp Comprehensive Organic Synthesis, ed. by B.M. Trost, I. Fleming (Pergamon, Oxford) 1991, p. 469.
- A. Domling, Chem. Rev. 2014, 106, 17.
- B.B. Toure, D.G. Hall, Chem. Rev. 2009, 109, 4439.
- A. Molla, S. Hussain, RSC Adv. 2014, 4, 29750.
- L. Bonsignore, G. Loy, D. Secei, A. Caligano,? Eur. J. Med. Chem. 1993, 28, 517.
- J. Bloxham, C.P. Dell, C.W. Smith, Heterocycles 1994, 38, 399.
- C.S. Konkoy, D.B. Fick, S.X. Cai, N.C. Lan, J.F.W. Keana? Int Appl WO 0075123, 2000; Chem. Abstr. 2001, 29313a.
- Y. Tang, J. Oppenheimer, Z. Song, L. You, X. Zhang, R.P. Hsung, Tetrahedron 2006, 62, 10785.
- E.J. Jung, B.H. Park, Y.R. Lee,? Green. Chem. 2010, 12, 2003.
- K. Singh, J. Sing, H. Singh, Tetrahedron 1996, 52, 14273.
- A. Shaabani, S. Samadi, Z. Baderi, A. Rahamati, Catal. Lett. 2005, 104, 39.
- K. Gong, H.L. Wang,? J. Luo, Z.L. Liu, J. Hetrocycl. Chem.? 2009, 46, 1145.
- S. Abdolmohammadi, S. Balalaie, Tetrahedron Lett. 2007, 48, 3299.
- S. Kumar, D. Hernandez, B. Hoa, Y. Lee, J.S. Yang, A. McCurdy, Org. Lett. 2008, 10, 3761.
- M. Rawat, V. Prutyanov, W.D. Wulff, J. Am. Chem. Soc. 2006, 128, 11044.
- O.A. Fedorova, F. Maure, A.V. Chebunkova, Y.P. Strokach, T.M. Valova, L.G. Kuzmina, J.A.K. Howard, M. Wenzel, K. Gloe, V. Lokshin, A. Samat, J. Phys. Org. Chem. 2007, 20, 469.
- R.S. Bhosale, C.V. Magar, K.S. Solanke, S.B. Mane, S.S. Choudhary, R.P. Pawar, Synth. Commun. 2007, 37, 4353.
- T.-S. Jin, A.-Q. Wang, F. Shi, L.-S. Han, L.-B. Liu, T.-S.? Li, ARKIVOC 2006, xiv, 78.
- I. Devi, P.J. Bhuyan, Tetrahedron 2004, 45(47), 8625.
- H. Jiang, S.J. Tu, F. Fang, X.S. Wang, Chin. J. Org. Chem. 2003, 24, 1458.
- J.F. Zhou, S.J. Tu, Y. Gao, Chin. J. Org. Chem. 2001, 21, 742.
- T.J. Jin, J.C. Xiao, S.J. Wang, T.S. Li, Synlett. 2003, 13, 2001.
- S. Abdolmohammadi, S. Balalaie, Synth. Commun. 2007, 37, 1097.
- M. Lande, S. Rathod, B. Arbad, Chin. J. Catal. 2010, 31, 631.
- L. Fotouhi, M.M. Heravi, A. Fatehi, K. Bakhtiari, Tetrahedron Lett. 2007, 48, 5379.
- A. Hasaninejad, A.P. Zare, A.A. Khalafi-Nezhad, A.N. Shirazi, A.R.M. Zare, Pol. J. Chem. 2008, 82, 565.
- B. Karami,? S.J. Khodabahshi, Serb. Chem. Soc. 2011, 76(9), 1191.
- A. Ramazani, N. Noshiranzadeh, Phosphorus, Sulfur, and Silicon and the Related Elements. 2003, 178(6), 1321.
- S. S.Gholap, S. R. Ugale, ChemistrySelect, 2017, 2(24), 7445-7449. (b) S. S.Gholap, S. R.Ugale, Chem. Pap. 2017. Doi:10.1007/s11696-017-0237-1. (c) S. S.Gholap, N. Gunjal, Arabian. J. Chem. 2017, 10, S2750-S2753. (d) S. S.Gholap, Y. R. Sadaphal, Sensors and Actuators B. 2017, 253, 173-179. (e) S. S. Gholap, Eur. J. Med. Chem. 2016, 110, 13-31. (f) S. S. Gholap, Gunjal, N. Iranian J. Catal. 2016, 8, 147-152. (g) S. S.Ghola p, V. D. Dhakane, U. P. Deshmukh, H. V. Chavan, B. P. Bandgar, C R Chim 2014, 17, 431-436. (h) S. S. Gholap, U. P. Deshmukh, Iranian J. Catal. 2013, 3, 171-176. (i) S. S. Gholap, V. D. Dhakane, Sandeep S. Gholap, Jordon J. Chem. 2012, 7(3), 279-285. (j) S. S. Gholap, V. D. Dhakane, S. N. Shelke, M. S. Tambe, Bull. Catal. Soc. India 2012, 11, 50. j) S. S. Gholap, Heterocycl Lett. 2012, 2(3), 461. (l) S. S. Gholap, C. H. Gill, G. R. Pandhare, Indian J. Heterocycl. Chem. 2009, 18, 279.
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