Publication: Reactions of acid Chlorides/Ketenes with 2-substituted 4,5-Dihydro-4,4-dimethyl-1,3-thiazoles: Formation of Penam derivatives
Reactions of acid Chlorides/Ketenes with 2-substituted 4,5-Dihydro-4,4-dimethyl-1,3-thiazoles: Formation of Penam derivatives
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Shi, J., Linden, A., & Heimgartner, H. (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. https://doi.org/10.1002/hlca.201300165
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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
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Shi, J., Linden, A., & Heimgartner, H. (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. https://doi.org/10.1002/hlca.201300165