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Reactions of acid Chlorides/Ketenes with 2-substituted 4,5-Dihydro-4,4-dimethyl-1,3-thiazoles: Formation of Penam derivatives


Shi, Jungxing; Linden, Anthony; Heimgartner, Heinz (2013). Reactions of acid Chlorides/Ketenes with 2-substituted 4,5-Dihydro-4,4-dimethyl-1,3-thiazoles: Formation of Penam derivatives. Helvetica Chimica Acta, 96(8):1462-1481.

Abstract

Addition reactions of acid chlorides with various 2-substituted 4,5-dihydro-4,4-dimethyl-5-(methylsulfanyl)-1,3-thiazoles under basic conditions were studied. Two kinds of products were obtained from these additions, beta-lactams and non-beta-lactam adducts. When the reaction was carried out with 4,5-dihydro-1,3-thiazoles with a Ph substituent at C(2), the reaction proceeded via formal [2+2] cycloaddition and led to the correspoding beta-lactam. On the other hand, acid chlorides and 4,5-dihydro-1,3-thiazoles bearing an alpha-H-atom at the C(2)-substituent underwent C(alpha)- and/or N-addition reactions and furnished non-beta-lactam adducts, i.e., C(alpha)- and/or N-acylated 1,3-thiazolidines. The attempted transformations of sulfonyl esters of exo-6-hydroxy penams to endo-6-azido penams failed, although they were successful with mono-beta-lactams under the same conditions.

Abstract

Addition reactions of acid chlorides with various 2-substituted 4,5-dihydro-4,4-dimethyl-5-(methylsulfanyl)-1,3-thiazoles under basic conditions were studied. Two kinds of products were obtained from these additions, beta-lactams and non-beta-lactam adducts. When the reaction was carried out with 4,5-dihydro-1,3-thiazoles with a Ph substituent at C(2), the reaction proceeded via formal [2+2] cycloaddition and led to the correspoding beta-lactam. On the other hand, acid chlorides and 4,5-dihydro-1,3-thiazoles bearing an alpha-H-atom at the C(2)-substituent underwent C(alpha)- and/or N-addition reactions and furnished non-beta-lactam adducts, i.e., C(alpha)- and/or N-acylated 1,3-thiazolidines. The attempted transformations of sulfonyl esters of exo-6-hydroxy penams to endo-6-azido penams failed, although they were successful with mono-beta-lactams under the same conditions.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:August 2013
Deposited On:19 Aug 2013 06:32
Last Modified:05 Apr 2016 16:54
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.201300165

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