Tandem Reactions of 2-Methylimidazoline
and 1,2-Dimethylimidazoline with Various Benzoyl Chlorides

Guozhong Ye; Chunlong Chen; Sabornie Chatterjee; Willard E. Collier; Aihua Zhou; Yingquan Song; Debbie J. Beard; Charles U. Jr. Pittman

doi:10.1055/s-0029-1217048

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Synthesis 2010(1): 141-152
DOI: 10.1055/s-0029-1217048

PAPER

Tandem Reactions of 2-Methylimidazoline and 1,2-Dimethylimidazoline with Various Benzoyl Chlorides

Guozhong Ye*^a, Chunlong Chen^b, Sabornie Chatterjee^a, Willard E. Collier^a, Aihua Zhou^c, Yingquan Song^a, Debbie J. Beard^a, Charles U. Jr. Pittman *^a
^a Department of Chemistry, Mississippi State University, Starkville, MS 39762, USA
Fax: +1(662)3257611; e-Mail: cpittman@chemistry.msstate.edu; e-Mail: gye001@gmail.com;
^b Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
^c Pharmacy School, University of Wisconsin-Madison, Madison, WI 53706, USA

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Publication History

Received 19 July 2009
Publication Date:
19 October 2009 (online)

Abstract
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Abstract

The reactions of 2-methylimidazoline with excess benzoyl chlorides under mild conditions generated N,N′-diacyl-β-keto cyclic ketene-N,N′-acetals. Conversely, the corresponding reactions of 1,2-dimethylimidazoline under the same conditions stereoselectively formed the ring-opened (Z)-vinyl benzoates. The latter reactions feature the formation of carbon-carbon bonds, carbon-nitrogen bonds, and carbon-oxygen bonds in one sequential cascade.

Key words

acyl ketene-N,N′-acetal - carbon-carbon bond formation - 2-methylimidazoline - 1,2-dimethylimidazoline

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