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RESEARCH ARTICLE
Contents Vol 67(9)

Use of Ethyl (Benzothiazol-2-ylsulfonyl)acetate for Malonic Ester-type Syntheses of Carboxylic Acids and Esters*

Waleed M. Hussein A B and Ross P. McGeary A C
+ Author Affiliations
- Author Affiliations

A The University of Queensland, School of Chemistry and Molecular Biosciences, Brisbane, Qld 4072, Australia.

B Helwan University, Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Ein Helwan, Helwan, Cairo, 11795, Egypt.

C Corresponding author. Email: r.mcgeary@uq.edu.au

Australian Journal of Chemistry 67(9) 1222-1227 https://doi.org/10.1071/CH14085
Submitted: 20 February 2014  Accepted: 28 March 2014   Published: 12 May 2014

Abstract

A new methodology for the synthesis of substituted carboxylic acids is described. Alkylation of either ethyl (benzothiazol-2-ylsulfonyl)acetate or ethyl 2-(benzothiazol-2-ylsulfonyl)propionate was achieved with alkyl halides and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dichloromethane solution. These products were then desulfinated and hydrolysed in one-pot under mild conditions to give substituted acetic acids in good-to-excellent yields.


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