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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

1-Ethyl-3-Methylimidazolium Cyanoborohydride Catalyzed Solvent Free Microwave Assisted One Pot Multicomponent Synthesis of Tetrahydrobenzo[ b]Pyran Derivatives

Author(s): Rajesh K. Manjul, Vilas B. Gade*, Dhananjay N. Gaikwad, Dayanand M. Suryavanshi, Anjali S. Rajbhoj and Suresh T. Gaikwad*

Volume 19, Issue 6, 2022

Published on: 10 January, 2022

Page: [457 - 462] Pages: 6

DOI: 10.2174/1570178618666210405151600

Price: $65

Open Access Journals Promotions 2
Abstract

We present a facile and environmentally benign protocol for the synthesis of tetrahydrobenzo[ b]pyran derivatives via multicomponent condensation of dimedon, malononitrile and different aromatic aldehydes in the presence of 1-ethyl-3-methylimidazolium cyanoborohydride ([EMIm][BH3CN]) as catalyst under microwave irradiation. The one-pot synthesis, facile solvent-free condition and good isolated yield illustrate the utility of this green approach. The structural features are derived using analytical tools, including Fourier Transform Infrared Spectroscopy (FT‐IR) and 1H and 13C Nuclear Magnetic Resonance (NMR) Spectroscopy. Electronic synthesis of tetrahydrobenzo[b]pyran derivatives by using catalytic action of 1-ethyl-3-methylimidazolium cyanoborohydride has been used to obtain maximum yield.

Keywords: Tetrahydrobenzo[b]pyran, microwave irradiation, solvent free, ionic liquid, FT-IR, TLC.

Graphical Abstract
[1]
Lennine, R.M.; Wender, A.S. Curr. Green Chem., 2016, 3(2), 120-132.
[http://dx.doi.org/10.2174/2213346103666160530143059]
[2]
DeSimone, J.M. Science, 2002, 297(5582), 799-803.
[http://dx.doi.org/10.1126/science.1069622] [PMID: 12161645]
[3]
Zhu, J. Bienaym é, H. Multicomponent Reactions; Wiley-VCH: Weinheim, 2005.
[http://dx.doi.org/10.1002/3527605118]
[4]
Tron, G.C.; Minassi, A.; Appendino, G. Eur. J. Org. Chem., 2011, 28, 5541-5550.
[http://dx.doi.org/10.1002/ejoc.201100661]
[5]
Giernoth, R. Angew. Chem. Int. Ed., 2010, 49, 2834-2839.
[http://dx.doi.org/10.1002/anie.200905981]
[6]
Shiramizu, M.; Toste, F.D. Angew. Chem. Int. Ed., 2013, 52, 12905-12909.
[http://dx.doi.org/10.1002/anie.201307564]
[7]
Singh, M.S.; Chowdhury, S. RSC Advances, 2012, 2, 4547-4592.
[http://dx.doi.org/10.1039/c2ra01056a]
[8]
Orha, L.; Akien, G.; István, T.H. Handbook of green Chemis-try; Li, C.J; Wiley-VCH: Weinheim, 2010.
[9]
Kappe, C.O. Chem. Soc. Rev., 2008, 37, 1127-1139.
[http://dx.doi.org/10.1039/b803001b] [PMID: 18497926]
[10]
Gawande, M.B.; Shelke, S.N.; Zboril, R.; Varma, R.S. Acc. Chem. Res., 2014, 47(4), 1338-1348.
[http://dx.doi.org/10.1021/ar400309b] [PMID: 24666323]
[11]
Dastan, A.; Kulkarni, A.; Török, B. Green Chem., 2012, 14, 17-37.
[http://dx.doi.org/10.1039/C1GC15837F]
[12]
Kulkarni, A.; Török, B. Green Chem., 2010, 12, 875-878.
[http://dx.doi.org/10.1039/c001076f]
[13]
Sarveswari, S.; Vijaykumar, V. J. Chin. Chem. Soc. (Taipei), 2012, 59, 66-71.
[http://dx.doi.org/10.1002/jccs.201100162]
[14]
Gelen, E.; De Kanter, F.J.J.; Schmitz, R.F.; Sliedregt, L.A.J.M.; Van Steen, B.J.; Kruse, C.G.; Leurs, R.; Groen, M.B.; Orru, R.V.A. Mol. Divers., 2006, 10, 17-22.
[http://dx.doi.org/10.1007/s11030-006-8695-3] [PMID: 16404525]
[15]
Rughuvanshi, D.S.; Singh, K.N. Indian J. Chem., 2010, 49B, 1394-1397.
[16]
Kale, S.; Kahandal, S.; Disale, S.; Jayaram, R. Curr. Chem. Lett., 2012, 1, 69-80.
[http://dx.doi.org/10.5267/j.ccl.2012.3.002]
[17]
Majumder, A.; Gupta, R.; Jain, A. Green Chem. Lett. Rev., 2013, 6, 151-182.
[http://dx.doi.org/10.1080/17518253.2012.733032]
[18]
Chaudhari, A.S.; Parab, Y.S.; Patil, V.; Sekar, N.; Shukla, S.R. RSC Advances, 2012, 2, 12112-12117.
[http://dx.doi.org/10.1039/c2ra21803h]
[19]
Martínez-Palou, R. J. Mex. Chem. Soc., 2007, 51, 252-264.
[20]
Shirole, G.D.; Kadnor, V.A.; Thambe, A.S.; Shelke, S.N. Res. Chem. Intermed., 2016, 43(2), 1089-1098.
[http://dx.doi.org/10.1007/s11164-016-2684-7]
[21]
Green, G.R.; Evans, J.M.; Vong, A.K.; Katritzky, A.R.; Rees, C.W.; Scriven, E.F.V. Comprehensive Heterocyclic Chemistry II; Pergamon Press: Oxford, 1995, Vol. 5, .
[22]
Andreani, L.L.; Lapi, E. Boll. Chim. Farm., 1960, 99, 583-586.
[PMID: 13759798]
[23]
Zhang, Y.L.; Chen, B.Z.; Zheng, K.Q. Yao Xue Xue Bao, 1982, 17(1), 17-22.
[PMID: 7090821]
[24]
Zhang, Y.L.; Chen, B.Z.; Zheng, K.Q.; Xu, M.L.; Lei, X.H. Chem. Abstr., 1982, 96.
[25]
Bonsignore, L.; Loy, G.; Secci, D.; Calignano, A. Eur. J. Med. Chem., 1993, 28, 517-520.
[http://dx.doi.org/10.1016/0223-5234(93)90020-F]
[26]
Konkoy, C.S.; Fick, D.B.; Cai, S.X.; Lan, N.C.; Keana, J.F.W. Chem. Abstr., 2000, 134.
[27]
Hatakeyama, S.; Ochi, N.; Numata, H.; Takano, S. J. Chem. Soc. Chem. Commun., 1988, 1202-1204.
[http://dx.doi.org/10.1039/C39880001202]
[28]
Armesto, D.; Horspool, W.M.; Martin, N.; Ramos, A.; Seaone, C. J. Org. Chem., 1989, 54, 3069-3072.
[http://dx.doi.org/10.1021/jo00274a021]
[29]
Hafez, E.A.A.; Elnagdi, M.H.; Elagamey, A.G.A. Heterocycles, 1987, 26, 903-907.
[30]
Hekmatshoar, R.; Majedi, S.; Bakhtiari, K. Catal. Commun., 2008, 9, 307-310.
[http://dx.doi.org/10.1016/j.catcom.2007.06.016]
[31]
Jin, T.S.; Wang, A.Q.; Shi, F.; Han, L.S.; Liu, L.B.; Li, T.S. ARKIVOC, 2006, (xiv), 78-86.
[http://dx.doi.org/10.3998/ark.5550190.0007.e11]
[32]
Devi, I.; Bhuyan, P.J. Tetrahedron Lett., 2004, 45, 8625-8627.
[http://dx.doi.org/10.1016/j.tetlet.2004.09.158]
[33]
Balalaie, S. Sheikh-Ahmadi, M.; Bararjanian, M. Catal. Commun., 2007, 8, 1724-1728.
[http://dx.doi.org/10.1016/j.catcom.2007.01.034]
[34]
Rong, L. Synth. Commun., 2006, 36, 2363-2369.
[http://dx.doi.org/10.1080/00397910600640230]
[35]
Zhuang, Q.Y.; Wu, N.; Shi, D.Q.; Tu, S.J.; Wang, X.S. Youji Huaxue, 2006, 26, 1217-1220.
[36]
Wang, X.S.; Shi, D.Q.; Tu, S.J.; Yao, C.S. Synth. Commun., 2003, 33, 119-126.
[http://dx.doi.org/10.1081/SCC-120015567]
[37]
Lian, X.Z.; Huang, Y.; Li, Y.Q.; Zheng, W.J. Monatsh. Chem., 2008, 139, 129-131.
[http://dx.doi.org/10.1007/s00706-007-0706-2]
[38]
Singh, K.; Singh, J.; Singh, H. Tetrahedron, 1996, 52, 14273-14280.
[http://dx.doi.org/10.1016/0040-4020(96)00879-4]
[39]
Balalaie, S.; Bararjanian, M. Sheikh-Ahmadi, M.; Hekmat, S.; Salehi, P. Synth. Commun., 2007, 37, 1097-1108.
[http://dx.doi.org/10.1080/00397910701196579]
[40]
Jin, T.S.; Wang, A.Q.; Wang, X.; Zhang, J.S.; Li, T.S. Synlett, 2004, 5, 871-873.
[http://dx.doi.org/10.1055/s-2004-820025]
[41]
Gade, V.B.; Rathi, A.K.; Bhalekar, S.B.; Tucek, J.; Tomanec, O.; Varma, R.S.; Zboril, R.; Shelke, S.N.; Gawande, M.B. ACS Sustain. Chem.& Eng., 2017, 5(4), 3314-3320.
[http://dx.doi.org/10.1021/acssuschemeng.6b03167]
[42]
Gade, V.B.; Goswami, A.; Varma, R.S.; Shelke, S.N.; Gawande, M.B. Nanomaterials (Basel), 2018, 8, 246.
[http://dx.doi.org/10.3390/nano8040246]
[43]
Chine, S.S.; Patil, C.S.; Gade, V.B. Curr. Catal., 2018, 7, 194-201.
[http://dx.doi.org/10.2174/2211544707666180918153941]

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