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Synthesis of Multi-Substituted 4,5-Dihydrofurans: Microwave Assisted Reaction of β-Ketonitriles, Aldehydes and Pyridinium Phenacyl Salts via [1+1+3] Knoevenagel-Michael-Oxa-Michael Cyclization Triple Cascade Sequence
Corresponding Author(s) : Somarapu Vijaya Laxmi
Asian Journal of Chemistry,
Vol. 35 No. 1 (2023): Vol 35 Issue 1
Abstract
A microwave assisted protocol for the development of fully substituted dihydrofurans has been explained as a three component triple cascade reaction between pyridinium ylide, phenacyl nitriles and aldehydes. This [1+1+3] annulation protocol produced the dihydrofurans having two stereocentres. A total of 14 molecules have been synthesized with high chemical yields.
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- L.F. Tietze, Chem. Rev., 96, 115 (1996); https://doi.org/10.1021/cr950027e
- N. Halland, P.S. Aburel and K.A. Jorgensen, Angew. Chem. Int. Ed., 43, 1272 (2004); https://doi.org/10.1002/anie.200353364
- V.B. Gudise, P.C. Settipalli, Y.P. Reddy and S. Anwar, ChemistrySelect, 6, 13589 (2021); https://doi.org/10.1002/slct.202103885
- P.C. Settipalli, Y.P. Reddy, V.B. Gudise and S. Anwar, ChemistrySelect, 6, 47 (2021); https://doi.org/10.1002/slct.202004619
- S. Anwar, L.-T. Lin, V. Srinivasadesikan, V.B. Gudise and K. Chen, RSC Adv., 11, 38648 (2021); https://doi.org/10.1039/D1RA07165C
- V.B. Gudise, P.C. Settipalli, E. Reddy and S. Anwar, Eur. J. Org. Chem., 2019, 2234 (2019); https://doi.org/10.1002/ejoc.201801709
- S.F. Basha, T.N. Prasad, V.B. Gudise, V.S. Kumar, N. Mulakayala and S. Anwar, Synth. Commun., 49, 3181 (2019); https://doi.org/10.1080/00397911.2019.1659973
- P. Saha, A. Biswas, N. Molleti and V.K. Singh, J. Org. Chem., 80, 11115 (2015); https://doi.org/10.1021/acs.joc.5b01751
- R. Karmakar, A. Suneja and V.K. Singh, Org. Lett., 18, 2636 (2016); https://doi.org/10.1021/acs.orglett.6b01057
- V.S. Kumar, V.B. Gudise, P.C. Settipalli, E.K. Reddy, S.F. Basha, Y.P. Reddy, V. Srinivasadesikan, S.-L. Lee and S. Anwar, ChemistrySelect, 5, 3080 (2020); https://doi.org/10.1002/slct.201904618
- D. Enders, M.R.M. Hüttl, C. Grondal and G. Raabe, Nature, 441, 861 (2006); https://doi.org/10.1038/nature04820
- S.M. Yang, Y.L. Tsai, G.M. Reddy, L. Mohlmann and W. Lin, J. Org. Chem., 82, 9182 (2017); https://doi.org/10.1021/acs.joc.7b01415
- S. Mukherjee, A. Ghosh, U.K. Marelli and A.T. Biju, Org. Lett., 20, 2952 (2018); https://doi.org/10.1021/acs.orglett.8b00998
- M. Bakthadoss, D. Kannan and R. Selvakumar, Chem. Commun., 49, 10947 (2013); https://doi.org/10.1039/c3cc45502e
- P. Kotame, B.-C. Hong, J.-H. Liao, J.-H., Tetrahedron Lett., 50, 704 (2020); https://doi.org/10.1016/j.tetlet.2008.11.106
- D. Enders, R. Krull and W. Bettray, Synthesis, 567 (2010); https://doi.org/10.1055/s-0029-1217146
- N. Sundaravelu, S. Guha and G. Sekar, J. Org. Chem., 85, 5895 (2020); https://doi.org/10.1021/acs.joc.0c00183
- S.K. Bankar, J. Mathew and S.S.V. Ramasastry, Chem. Commun., 52, 5569 (2016); https://doi.org/10.1039/C6CC01016D
- Y. Tangella, K.L. Manasa, V. Laxma Nayak, M. Sathish, B. Sridhar, A. Alarifi, N. Nagesh and A. Kamal, Org. Biomol. Chem., 15, 6837 (2017); https://doi.org/10.1039/C7OB01456B
- A.E. Wright, N.S. Burres and G.K. Schulte, Tetrahedron Lett., 30, 3491 (1989); https://doi.org/10.1016/S0040-4039(00)99421-8
- K.M. Marks, E.S. Park, A. Arefolov, K. Russo, K. Ishihara, J.E. Ring, J. Clardy, A.S. Clarke and H.E. Pelish, J. Nat. Prod., 74, 567 (2011); https://doi.org/10.1021/np100429s
- C.P.V. Freire, S.B. Ferreira, N.S.M. de Oliveira, A.B.J. Matsuura, I.L. Gama, F.C. da Silva, M.C.B.V. de Souza, E.S. Lima and V.F. Ferreira, MedChemComm, 1, 229 (2010); https://doi.org/10.1039/c0md00074d
- E.D. Coy, L.E. Cuca and M. Sefkow, Bioorg. Med. Chem. Lett., 19, 6922 (2009); https://doi.org/10.1016/j.bmcl.2009.10.069
- L. Dutta, M. Sharma and PJ. Bhuyan, Tetrahedron, 72, 6654 (2016); https://doi.org/10.1016/j.tet.2016.08.084
- C.-P. Chuang and K.-P. Chen, Tetrahedron, 68, 1401 (2012); https://doi.org/10.1016/j.tet.2011.12.035
- A.T. Khan, M. Lal and R.S. Basha, Synthesis, 45, 406 (2013); https://doi.org/10.1055/s-0032-1316837
- P. Gunasekaran, K. Balamurugan, S. Sivakumar, S. Perumal, J.C. Menéndez and A.I. Almansour, Green Chem., 14, 750 (2012); https://doi.org/10.1039/C2GC16517A
- S. Ahadi, T. Kamranifard, M. Armaghan, H.R. Khavasi and A. Bazgir, RSC Adv., 4, 7296 (2014); https://doi.org/10.1039/c3ra45795h
- J.-R. Ma, W.-M. Shu, K.-L. Zheng, F. Ni, G.-D. Yin and A.-X. Wu, Org. Biomol. Chem., 13, 4976 (2015); https://doi.org/10.1039/C5OB00163C
- S. Sathiyamoorthi, A.I. Almansour, S.K. Raju, A. Natarajan and R.R. Kumar, Synth. Commun., 51, 234 (2021); https://doi.org/10.1080/00397911.2020.1821226
- M.R. Demidov, V.A. Osyanin, D.V. Osipov and Y.N. Klimochkin, J. Org. Chem., 86, 7460 (2021); https://doi.org/10.1021/acs.joc.1c00423
References
L.F. Tietze, Chem. Rev., 96, 115 (1996); https://doi.org/10.1021/cr950027e
N. Halland, P.S. Aburel and K.A. Jorgensen, Angew. Chem. Int. Ed., 43, 1272 (2004); https://doi.org/10.1002/anie.200353364
V.B. Gudise, P.C. Settipalli, Y.P. Reddy and S. Anwar, ChemistrySelect, 6, 13589 (2021); https://doi.org/10.1002/slct.202103885
P.C. Settipalli, Y.P. Reddy, V.B. Gudise and S. Anwar, ChemistrySelect, 6, 47 (2021); https://doi.org/10.1002/slct.202004619
S. Anwar, L.-T. Lin, V. Srinivasadesikan, V.B. Gudise and K. Chen, RSC Adv., 11, 38648 (2021); https://doi.org/10.1039/D1RA07165C
V.B. Gudise, P.C. Settipalli, E. Reddy and S. Anwar, Eur. J. Org. Chem., 2019, 2234 (2019); https://doi.org/10.1002/ejoc.201801709
S.F. Basha, T.N. Prasad, V.B. Gudise, V.S. Kumar, N. Mulakayala and S. Anwar, Synth. Commun., 49, 3181 (2019); https://doi.org/10.1080/00397911.2019.1659973
P. Saha, A. Biswas, N. Molleti and V.K. Singh, J. Org. Chem., 80, 11115 (2015); https://doi.org/10.1021/acs.joc.5b01751
R. Karmakar, A. Suneja and V.K. Singh, Org. Lett., 18, 2636 (2016); https://doi.org/10.1021/acs.orglett.6b01057
V.S. Kumar, V.B. Gudise, P.C. Settipalli, E.K. Reddy, S.F. Basha, Y.P. Reddy, V. Srinivasadesikan, S.-L. Lee and S. Anwar, ChemistrySelect, 5, 3080 (2020); https://doi.org/10.1002/slct.201904618
D. Enders, M.R.M. Hüttl, C. Grondal and G. Raabe, Nature, 441, 861 (2006); https://doi.org/10.1038/nature04820
S.M. Yang, Y.L. Tsai, G.M. Reddy, L. Mohlmann and W. Lin, J. Org. Chem., 82, 9182 (2017); https://doi.org/10.1021/acs.joc.7b01415
S. Mukherjee, A. Ghosh, U.K. Marelli and A.T. Biju, Org. Lett., 20, 2952 (2018); https://doi.org/10.1021/acs.orglett.8b00998
M. Bakthadoss, D. Kannan and R. Selvakumar, Chem. Commun., 49, 10947 (2013); https://doi.org/10.1039/c3cc45502e
P. Kotame, B.-C. Hong, J.-H. Liao, J.-H., Tetrahedron Lett., 50, 704 (2020); https://doi.org/10.1016/j.tetlet.2008.11.106
D. Enders, R. Krull and W. Bettray, Synthesis, 567 (2010); https://doi.org/10.1055/s-0029-1217146
N. Sundaravelu, S. Guha and G. Sekar, J. Org. Chem., 85, 5895 (2020); https://doi.org/10.1021/acs.joc.0c00183
S.K. Bankar, J. Mathew and S.S.V. Ramasastry, Chem. Commun., 52, 5569 (2016); https://doi.org/10.1039/C6CC01016D
Y. Tangella, K.L. Manasa, V. Laxma Nayak, M. Sathish, B. Sridhar, A. Alarifi, N. Nagesh and A. Kamal, Org. Biomol. Chem., 15, 6837 (2017); https://doi.org/10.1039/C7OB01456B
A.E. Wright, N.S. Burres and G.K. Schulte, Tetrahedron Lett., 30, 3491 (1989); https://doi.org/10.1016/S0040-4039(00)99421-8
K.M. Marks, E.S. Park, A. Arefolov, K. Russo, K. Ishihara, J.E. Ring, J. Clardy, A.S. Clarke and H.E. Pelish, J. Nat. Prod., 74, 567 (2011); https://doi.org/10.1021/np100429s
C.P.V. Freire, S.B. Ferreira, N.S.M. de Oliveira, A.B.J. Matsuura, I.L. Gama, F.C. da Silva, M.C.B.V. de Souza, E.S. Lima and V.F. Ferreira, MedChemComm, 1, 229 (2010); https://doi.org/10.1039/c0md00074d
E.D. Coy, L.E. Cuca and M. Sefkow, Bioorg. Med. Chem. Lett., 19, 6922 (2009); https://doi.org/10.1016/j.bmcl.2009.10.069
L. Dutta, M. Sharma and PJ. Bhuyan, Tetrahedron, 72, 6654 (2016); https://doi.org/10.1016/j.tet.2016.08.084
C.-P. Chuang and K.-P. Chen, Tetrahedron, 68, 1401 (2012); https://doi.org/10.1016/j.tet.2011.12.035
A.T. Khan, M. Lal and R.S. Basha, Synthesis, 45, 406 (2013); https://doi.org/10.1055/s-0032-1316837
P. Gunasekaran, K. Balamurugan, S. Sivakumar, S. Perumal, J.C. Menéndez and A.I. Almansour, Green Chem., 14, 750 (2012); https://doi.org/10.1039/C2GC16517A
S. Ahadi, T. Kamranifard, M. Armaghan, H.R. Khavasi and A. Bazgir, RSC Adv., 4, 7296 (2014); https://doi.org/10.1039/c3ra45795h
J.-R. Ma, W.-M. Shu, K.-L. Zheng, F. Ni, G.-D. Yin and A.-X. Wu, Org. Biomol. Chem., 13, 4976 (2015); https://doi.org/10.1039/C5OB00163C
S. Sathiyamoorthi, A.I. Almansour, S.K. Raju, A. Natarajan and R.R. Kumar, Synth. Commun., 51, 234 (2021); https://doi.org/10.1080/00397911.2020.1821226
M.R. Demidov, V.A. Osyanin, D.V. Osipov and Y.N. Klimochkin, J. Org. Chem., 86, 7460 (2021); https://doi.org/10.1021/acs.joc.1c00423