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2-aryl-1,2-diazetidin-3-ones (aza-β-lactams) via grignard-induced cyclization of α-(2-arylhydrazino)-esters

✍ Scribed by Joachim G. Schantl; Martin Decristoforo; John J. Daly

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
267 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

The a-(2_arylhydrazino)-esters 1 react with i-propylmagnesium iodide to furnish 2-aryl-1,2-diazetidin-3-ones 2, which-in turn undergo ring-opening with methyllithium affording a-(2-arylhydrazino)-ketones 3.

As part of a program to study a-(2-arylhydrazino)-alkanone arylhydrazonesl the synthesis of a-(2-arylhydrazino)-ketones was devised, and thereby a novel access to the four-membered heterocyclic system of 1,2-diazetidin-3-ones (aza-8-lactams) was found.

Following standard procedures the 2-arylhydrazino isobutyric esters 1 are readily available starting compounds containing the required 1,2-disubstituted hydrazine moiety as has been unambiguously proved by the conversion into the corresponding arylazo ester2. The reaction of the esters 1 with Grignard compounds was anticipated to provide the desired a-(2-arylhydrazino)-ketones. In fact, the reaction of the esters 1 with methylmagnesium iodide furnished a mixture of two products (ratio 1:4): Beside the methylketones 3, the 1,2diazetidin-3-ones 2 were formed predominantly.

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