Synthesis of β-Lactam from Acyl(Arylcarbamoyl)-S,S-bis(alkylketene) Dithioacetal: Revised Structure of the Product from Thermal Cyclization of Acyl(Arylcarbamoyl)-S,S-bis(alkylketene) Dithioacetal

Abstract

The structure of the quinolinone obtained from thermal cyclization of ketene dithioacetal has been revised by X-ray crystallographic analysis as 4-quinolinone instead of the previously reported 2-quinolinone. In the course of study on the mechanistic feature of the thermal cyclization, highly substituted β-lactams were obtained by alkylating β-lactam anion with MEMCl, MOMCl, or MeI in the presence of NaH.

Key words

thermal cyclization - ketene dithioacetal - β-lactam - 4-quinolinone

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X-ray crystal structure analysis of 1g, (E)-9a and (Z)-9a: atomic coordinates, bond lengths and angles, anisotropic displacement parameters, hydrogen coordinates, torsion angles have been deposited at Cambridge Crystallographic Data Centre 12, Union Road, Cambridge CB2 1EZ, UK, under deposition number CCDC 201216 for 1g; CCDC 201217 for (E)-9a; and CCDC 201218 for (Z)-9a. Fax: [phone], E-mail: [e-mail].