Abstract

Background: -lactams have been primarily utilized as a leading class of effective antibiotics. They have been found to show activity against various diseases, prompting the scientific community to prioritise innovative protocols for their synthesis. The general and well-known synthetic strategy involves the classical Staudinger reaction exhibiting [2+2] cycloaddition reaction. However, the protocol utilizes stoichiometric excess of base for efficient product formation.

Objective: A smarter and more acceptable approach for the synthesis of -lactams would be to reduce the excess base to a catalytic amount, furnishing a catalytic version of the Staudinger reaction. The modified version can eliminate the hazards arising out of excess use of the base, ultimately promoting the environmentally benign approach.

Methods: With this hypothesis, a base-catalyzed approach in dimethyl formamide (DMF) towards the synthesis of -lactam via Staudinger reaction has been endorsed under moderate reaction conditions.

Results: The scope of the substrates was explored with both electron-withdrawing and electronreleasing substitutions in the formation of -lactam. The reduction of the base amount from stoichiometric to catalytic amount was justified by the involvement of DMF in generating the basic condition for the reaction.

Conclusion: It was hypothesized that the decomposition of DMF under the base-catalysed reaction condition can generate dimethylamine, which produces the required basic environment.

Keywords: Base-catalysed, -lactams, staudinger reaction, [2+2] cycloaddition reaction, catalytic, antibiotics, DMF activation, triethylamine, immine, acetyl chloride.