Vol. 31, No. 4 (2019)
Microwave Assisted One Pot Synthesis of 3,4-Dihydropyrano[c]chromene Derivatives 833
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nitrile and methanol. It was observed that ethanol medium is
the best reaction medium among the polar solvents used in
demonstration and reaction proceeded very smoothly which
gave the desired product with excellent yield within short
reaction time (entry 24, Table-2). The aryl aldehydes which
possess electron withdrawing substituent gave high yield as
compared to aromatic aldehydes bearing electron donating
substituent as illustrated in Table-3.
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https://doi.org/10.1002/ardp.200600057.
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Reaction mechanism: In this reaction, [Emim]OH acts
as the base, malononitrile and 4-hydroxycoumarine undergo
enolization from a to b. The b on cross aldol condensation with
c gave intermediate d. The intermediate d on E cB elimination
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6. M. Ziarani and Ghodsi, Iran. J. Chem. Chem. Eng., 30, 59 (2011).
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https://doi.org/10.1016/j.tetlet.2009.04.125.
gives intermediate e. The intermediate e with malononitrile
on Michael addition gives intermediate f, which on cyclization
gives intermediate g and after protonation forms intermediate h.
Finally h on rearrangement converted into dihydropyrano[2,3-c]-
chromene (Scheme-II).
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9. S. Abdolmohammadi and S. Balalaie, Tetrahedron Lett., 48, 3299
(
2007);
https://doi.org/10.1016/j.tetlet.2007.02.135.
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ACKNOWLEDGEMENTS
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One of the authors (DSB) is thankful to CSIR, New Delhi,
India for the financial support under senior research fellowship
SRF). The authors are thankful to Dr. S.N. Thore, Principal,
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(
Deogiri College,Aurangabad, India for encouraging and provi-
ding the research facilities. The authors also extended their
thanks to Dr. (Mrs.) Hemlata J.Wankede (Director, Government
Institute of Forensic Science) for providing the sophisticated
instrumentation facilities.
https://doi.org/10.1016/j.jtusci.2014.09.008.
3. D.S. Patel, J.R. Avalani and D.K. Raval, J. Saudi Chem. Soc., 20S1,
s401 (2013);
https://doi.org/10.1016/j.jscs.2012.12.008.
4. S. Paul, P. Bhattacharyya and A.R. Das, Tetrahedron Lett., 52, 4636
(2011);
https://doi.org/10.1016/j.tetlet.2011.06.101.
5. A. Azarifar, R. Nejat-Yami, M. Al Kobaisi and D. Azarifar, J. Iran
Chem. Soc., 10, 439 (2013);
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CONFLICT OF INTEREST
The authors declare that there is no conflict of interests
regarding the publication of this article.
https://doi.org/10.1007/s13738-012-0177-1.
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6. H.R. Shaterian and M. Honarmand, Synth. Commun., 41, 3573 (2011);
https://doi.org/10.1080/00397911.2010.519594.
7. N.G. Khaligh, S.B.A. Hamid and S.J.J. Titinchi, Polycycl. Aromat.
Compd., 37, 31 (2017);
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