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Knoevenagel Condensation Shadowed by Michael Addition & O-Alkylation of Resorcinol, Malononitrile and Benzadehyde to form Pyrrolidine, Piperidine and Morpholine Substituted Benzopyran Derivatives in Dry K2CO3
Corresponding Author(s) : Jaya Pandey
Asian Journal of Chemistry,
Vol. 31 No. 7 (2019): Vol 31 Issue 7
Abstract
A condensation reaction of resorcinol, malononitrile and benzaldehyde in presence of sodium carbonate at room temperature on vigorous stirring gives 2-amino-7-hydroxy-4-phenyl-4H-1-benzopyran-3-carbonitrile which on alkylation in presence of dry potassium carbonate in dry acetone at 70-80 ºC with 1,2-chloroethyl pyrrolidine, 1,2-chloroethyl piperidine, 1,2-chloroethyl morpholine gives corresponding novel compounds.
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- D. Andreou, M.G. Kallitsakis, E. Loukopoulos, C. Gabriel, G.E. Kostakis and I.N. Lykakis, J. Org. Chem., 83, 2104 (2018); https://doi.org/10.1021/acs.joc.7b03051.
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- A. G. Neo and C. F. Marcos, Org. Lett., 20, 3875 (2018); https://doi.org/10.1021/acs.orglett.8b01462.
- N.R. Candeias, P.M.S.D. Cal, V. André, M.T. Duarte, L.F. Veiros and P.M.P. Gois, Tetrahedron, 66, 2736 (2010); https://doi.org/10.1016/j.tet.2010.01.084.
- I.B. Masesane and S.O. Mihigo, Synth. Commun., 45, 1546 (2015); https://doi.org/10.1080/00397911.2015.1031249.
- Y. Ogiwara, K. Takahashi, T. Kitazawa and N. Sakai, J. Org. Chem., 80, 3101 (2015); https://doi.org/10.1021/acs.joc.5b00011.
- M. Pourmohammad and M. Mokhtary, C.R. Chim., 18, 554 (2015); https://doi.org/10.1016/j.crci.2014.09.008.
- M.R. Naimi-Jamal, S. Mashkouri and A. Sharifi, Mol. Divers., 14, 473 (2010); https://doi.org/10.1007/s11030-010-9246-5.
- J. Albadi, A. Razeghi, A. Mansournezhad and Z. Azarian, J. Nanostr. Chem., 3, 85 (2013); https://doi.org/10.1186/2193-8865-3-85.
- P. Wadhwa, A. Kharbanda and A. Sharma, Asian J. Org. Chem., 7, 634 (2018); https://doi.org/10.1002/ajoc.201700609.
- S. Lauzon, M. Li, H. Keipour and T. Ollevier, Eur. J. Org. Chem., 2018, 4536 (2018); https://doi.org/10.1002/ejoc.201800780.
- R. Singh, Y. Thopate, D. Equbal and A.K. Sinha, Adv. Synth. Catal., 360, 4412 (2018); https://doi.org/10.1002/adsc.201801150.
- Y. Zuo, N. Yang, X. Huang, C. Hu and Z. Su, J. Org. Chem., 83, 4628 (2018); https://doi.org/10.1021/acs.joc.8b00387.
- Y.Z. Hua, J.W. Chen, H. Yang and M.C. Wang, J. Org. Chem., 83, 1160 (2018); https://doi.org/10.1021/acs.joc.7b02599.
- H.R. Safaei, M. Shekouhy, S. Rahmanpur and A. Shirinfeshan, Green Chem., 14, 1696 (2012); https://doi.org/10.1039/c2gc35135h.
- M.M. Kandeel, A.M. Kamal, E.K.A. Abdelall, H.A.H. Elshemy, Der Pharm. Chem., 4, 1653 (2012).
- A. Bouattour, M. Fakhfakh, S. Abid, L. Paquin, R.L. Guvel, A. Corlu, S. Ruchaud, S. Bach, H. Ammar and J.-P. Bazureau, ARKIVOC, 291 (2017); https://doi.org/10.24820/ark.5550190.p010.040.
References
D. Andreou, M.G. Kallitsakis, E. Loukopoulos, C. Gabriel, G.E. Kostakis and I.N. Lykakis, J. Org. Chem., 83, 2104 (2018); https://doi.org/10.1021/acs.joc.7b03051.
X.W. Zhang, W.L. Hu, S. Chen and X.G. Hu, Org. Lett., 20, 860 (2018); https://doi.org/10.1021/acs.orglett.7b04028.
A. G. Neo and C. F. Marcos, Org. Lett., 20, 3875 (2018); https://doi.org/10.1021/acs.orglett.8b01462.
N.R. Candeias, P.M.S.D. Cal, V. André, M.T. Duarte, L.F. Veiros and P.M.P. Gois, Tetrahedron, 66, 2736 (2010); https://doi.org/10.1016/j.tet.2010.01.084.
I.B. Masesane and S.O. Mihigo, Synth. Commun., 45, 1546 (2015); https://doi.org/10.1080/00397911.2015.1031249.
Y. Ogiwara, K. Takahashi, T. Kitazawa and N. Sakai, J. Org. Chem., 80, 3101 (2015); https://doi.org/10.1021/acs.joc.5b00011.
M. Pourmohammad and M. Mokhtary, C.R. Chim., 18, 554 (2015); https://doi.org/10.1016/j.crci.2014.09.008.
M.R. Naimi-Jamal, S. Mashkouri and A. Sharifi, Mol. Divers., 14, 473 (2010); https://doi.org/10.1007/s11030-010-9246-5.
J. Albadi, A. Razeghi, A. Mansournezhad and Z. Azarian, J. Nanostr. Chem., 3, 85 (2013); https://doi.org/10.1186/2193-8865-3-85.
P. Wadhwa, A. Kharbanda and A. Sharma, Asian J. Org. Chem., 7, 634 (2018); https://doi.org/10.1002/ajoc.201700609.
S. Lauzon, M. Li, H. Keipour and T. Ollevier, Eur. J. Org. Chem., 2018, 4536 (2018); https://doi.org/10.1002/ejoc.201800780.
R. Singh, Y. Thopate, D. Equbal and A.K. Sinha, Adv. Synth. Catal., 360, 4412 (2018); https://doi.org/10.1002/adsc.201801150.
Y. Zuo, N. Yang, X. Huang, C. Hu and Z. Su, J. Org. Chem., 83, 4628 (2018); https://doi.org/10.1021/acs.joc.8b00387.
Y.Z. Hua, J.W. Chen, H. Yang and M.C. Wang, J. Org. Chem., 83, 1160 (2018); https://doi.org/10.1021/acs.joc.7b02599.
H.R. Safaei, M. Shekouhy, S. Rahmanpur and A. Shirinfeshan, Green Chem., 14, 1696 (2012); https://doi.org/10.1039/c2gc35135h.
M.M. Kandeel, A.M. Kamal, E.K.A. Abdelall, H.A.H. Elshemy, Der Pharm. Chem., 4, 1653 (2012).
A. Bouattour, M. Fakhfakh, S. Abid, L. Paquin, R.L. Guvel, A. Corlu, S. Ruchaud, S. Bach, H. Ammar and J.-P. Bazureau, ARKIVOC, 291 (2017); https://doi.org/10.24820/ark.5550190.p010.040.