[2+2] cycloadditions of sorbyl tosylate with imines/1-azadienes: a one-pot domino approach for α-alkylidene-β-lactams and their computational studies and antimicrobial evaluation

Date
2018
Authors
Kumar, Y.
Bedi, P. M. S.
Singh, P.
Adeniyi, A. A.
Singh-Pillay, A.
Singh, P.
Bhargava, G.
Advisor
Supervisor
Co-Advisor
Co-Supervisor
Instructor
Source Title
ChemistrySelect
Print ISSN
Electronic ISSN
2365-6549
Publisher
Wiley-Blackwell
Volume
3
Issue
32
Pages
9484 - 9492
Language
English
Type
Article
Journal Title
Journal ISSN
Volume Title
Series
Abstract

The manuscript describes a straightforward and atom-efficient method for the synthesis of α-alkylidene-β-lactams using sorbyl tosylate and imines/1-azadienes at high temperature (80 °C). The Density functional theory calculations have shown the prevalence of the first order kinetics in these [2+2] cycloadditions to produce mixture of 3-butadienyl-azetidin-2ones and 3-but-2-enylidene-azetidin-2-ones in good yields. The 3-but-2-enylidene-azetidin-2-ones have also shown antimicrobial activity against the E. coli, S. aureus, P. aeruginosa, B. cereus and B. subtilis.

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Book Title
Keywords
Azadiene, Butadienylketene, Spirocycles, α-alkylidene-β-lactam, β-lactam
Citation
Published Version (Please cite this version)