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Microwave-Induced Bismuth Nitrate-Catalyzed Michael Reaction of 3-Amino β-Lactams with Enones
Corresponding Author(s) : Bimal Krishna Banik
Asian Journal of Chemistry,
Vol. 32 No. 2 (2020): Vol 32 Issue 2
Abstract
Microwave-induced bismuth nitrate-catalyzed reaction of 3-amino β-lactams with unsaturated ketones is performed in order to obtain substituted amino β-lactams. Amino β-lactams were obtained through the strategy of [2+2] ketene-imine cycloaddition followed by deprotection of phthalimido β-lactams with ethylene diamine.
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- G. Cardillo and C. Tomasini, Chem. Soc. Rev., 25, 117 (1996); https://doi.org/10.1039/CS9962500117.
- P. Hradil, J. Hlavac, M. Soural, M. Hajduch, M. Kolar and R. Vecerova, Mini-Rev. Med. Chem., 9, 696 (2009); https://doi.org/10.2174/138955709788452720.
- A. Kamath and I. Ojima, Tetrahedron, 68, 10640 (2012); https://doi.org/10.1016/j.tet.2012.07.090.
- N.C. Cohen, J. Med. Chem., 26, 259 (1983); https://doi.org/10.1021/jm00356a027.
- B.K. Banik and F.F. Becker, Bioorg. Med. Chem., 9, 593 (2001); https://doi.org/10.1016/S0968-0896(00)00297-2.
- B.K. Banik, S. Samajdar and F.F. Becker, Mol. Med. Rep., 3, 319 (2010); https://doi.org/10.3892/mmr_00000259.
- I. Banik, F.F. Becker and B.K. Banik, J. Med. Chem., 46, 12 (2003); https://doi.org/10.1021/jm0255825.
- I. Ojima, Acc. Chem. Res., 28, 383 (1995); https://doi.org/10.1021/ar00057a004.
- I. Ojima, E.S. Zuniga and J.D. Seitz, ed.: B.K. Banik, Advances in the Use of Enantiopure β-Lactams for the synthesis of Biologically Active Compounds of Medicinal Interests, In: β-Lactams: Unique Structures of Distinction for Novel Molecules, Topics in Heterocyclic Chemistry, Springer, vol. 30, pp. 1-63 (2013).
- B.K. Banik, Heterocycl. Lett., 4, 441 (2014).
- J.M. Betancort and C.F. Barbas, Org. Lett., 3, 3737 (2001); https://doi.org/10.1021/ol0167006.
- D. Almasi, D.A. Alonso, E. Gómez-Bengoa, Y. Nagel and C. Nájera, Eur. J. Org. Chem., 2328 (2007); https://doi.org/10.1002/ejoc.200700031.
- N. Srivastava and B.K. Banik, J. Org. Chem., 68, 2109 (2003); https://doi.org/10.1021/jo026550s.
- J.H. Clark, Green Chem., 1, 1 (1999); https://doi.org/10.1039/a807961g.
- A. Loupy, Microwaves in Organic Synthesis, Wiley-VCH Verlag GmbH & Co. KGaA, edn 2 (2008). https://doi.org/10.1002/9783527619559.
- C.O. Kappe, B. Pieber and D. Dallinger, Angew. Chem., 52, 1088 (2013); https://doi.org/10.1002/anie.201204103.
- D. Bandyopadhyay and B.K. Banik, eds.: G. Brahmachari, MicrowaveInduced Synthesis of Heterocycles of Medicinal Interests, In: Green Synthetic Approaches for Biologically Relevant Heterocycles, Elsevier, Chap. 19, pp. 517-557 (2014).
- A. Banik, M.S. Manhas, Z. Kaluza, K.J. Barakat and A.K. Rose, Tetrahedron Lett., 33, 3603 (1992); https://doi.org/10.1016/S0040-4039(00)92513-9.
- B.K. Bandyopadhyay, J. Cruz, R.N. Yadav and B.K. Banik, Molecules, 17, 11570 (2012); https://doi.org/10.3390/molecules171011570.
- B. Indrani, F.F. Becker and B.K. Banik, Mod. Chem. Appl., 5, 228 (2017); https://doi.org/10.4172/2329-6798.1000228.
References
G. Cardillo and C. Tomasini, Chem. Soc. Rev., 25, 117 (1996); https://doi.org/10.1039/CS9962500117.
P. Hradil, J. Hlavac, M. Soural, M. Hajduch, M. Kolar and R. Vecerova, Mini-Rev. Med. Chem., 9, 696 (2009); https://doi.org/10.2174/138955709788452720.
A. Kamath and I. Ojima, Tetrahedron, 68, 10640 (2012); https://doi.org/10.1016/j.tet.2012.07.090.
N.C. Cohen, J. Med. Chem., 26, 259 (1983); https://doi.org/10.1021/jm00356a027.
B.K. Banik and F.F. Becker, Bioorg. Med. Chem., 9, 593 (2001); https://doi.org/10.1016/S0968-0896(00)00297-2.
B.K. Banik, S. Samajdar and F.F. Becker, Mol. Med. Rep., 3, 319 (2010); https://doi.org/10.3892/mmr_00000259.
I. Banik, F.F. Becker and B.K. Banik, J. Med. Chem., 46, 12 (2003); https://doi.org/10.1021/jm0255825.
I. Ojima, Acc. Chem. Res., 28, 383 (1995); https://doi.org/10.1021/ar00057a004.
I. Ojima, E.S. Zuniga and J.D. Seitz, ed.: B.K. Banik, Advances in the Use of Enantiopure β-Lactams for the synthesis of Biologically Active Compounds of Medicinal Interests, In: β-Lactams: Unique Structures of Distinction for Novel Molecules, Topics in Heterocyclic Chemistry, Springer, vol. 30, pp. 1-63 (2013).
B.K. Banik, Heterocycl. Lett., 4, 441 (2014).
J.M. Betancort and C.F. Barbas, Org. Lett., 3, 3737 (2001); https://doi.org/10.1021/ol0167006.
D. Almasi, D.A. Alonso, E. Gómez-Bengoa, Y. Nagel and C. Nájera, Eur. J. Org. Chem., 2328 (2007); https://doi.org/10.1002/ejoc.200700031.
N. Srivastava and B.K. Banik, J. Org. Chem., 68, 2109 (2003); https://doi.org/10.1021/jo026550s.
J.H. Clark, Green Chem., 1, 1 (1999); https://doi.org/10.1039/a807961g.
A. Loupy, Microwaves in Organic Synthesis, Wiley-VCH Verlag GmbH & Co. KGaA, edn 2 (2008). https://doi.org/10.1002/9783527619559.
C.O. Kappe, B. Pieber and D. Dallinger, Angew. Chem., 52, 1088 (2013); https://doi.org/10.1002/anie.201204103.
D. Bandyopadhyay and B.K. Banik, eds.: G. Brahmachari, MicrowaveInduced Synthesis of Heterocycles of Medicinal Interests, In: Green Synthetic Approaches for Biologically Relevant Heterocycles, Elsevier, Chap. 19, pp. 517-557 (2014).
A. Banik, M.S. Manhas, Z. Kaluza, K.J. Barakat and A.K. Rose, Tetrahedron Lett., 33, 3603 (1992); https://doi.org/10.1016/S0040-4039(00)92513-9.
B.K. Bandyopadhyay, J. Cruz, R.N. Yadav and B.K. Banik, Molecules, 17, 11570 (2012); https://doi.org/10.3390/molecules171011570.
B. Indrani, F.F. Becker and B.K. Banik, Mod. Chem. Appl., 5, 228 (2017); https://doi.org/10.4172/2329-6798.1000228.