Issue 13, 1981

Synthesis of ethyl 3-methyl-7-oxo-4-oxo-4-oxa-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate and the reaction of 4-acetoxyazetidin-2-one with ethyl α-diazoacetoacetate

Abstract

Ethyl 3-methyl-7-oxo-4-oxa-1-azobicylco[3.2.0]-hept-2-ene-2-carboxylate (4) has been obtained by a four-step synthesis from 4-methylthioazetidin-2-one and has been compared with the products obtained from the rhodium(II) acetate-catalysed reaction of 4-acetoxy-azetidin-2-one with ethyl α-diazoacetoacetate; this latter reaction did not give compound (4), as was previously claimed, but yielded ethyl 2-(4-acetoxy-2-oxoazetidinyl)-3-oxobutyrate as the major β-lactam product.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1981, 642-643

Synthesis of ethyl 3-methyl-7-oxo-4-oxo-4-oxa-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate and the reaction of 4-acetoxyazetidin-2-one with ethyl α-diazoacetoacetate

G. Brooks, T. T. Howarth and E. Hunt, J. Chem. Soc., Chem. Commun., 1981, 642 DOI: 10.1039/C39810000642

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements