Transformations of penicillins. Part V. Reactions of olefin and acetylene derivatives with the sulphenic acid intermediates from penicillin S-oxides

Autor:	Caroline A. Robson, Ian R. Ager, Brian Edgar Looker, Peter G. Sammes, Gino Lucente, Ann Mowatt, David G. T. Greig, Graham Hewitt, Derek H. R. Barton, William George Elphi Underwood, Michael V. Taylor
Rok vydání:	1973
Předmět:	Dimethyl acetylenedicarboxylate Substitution reaction Olefin fiber Dihydropyran Norbornadiene Substituent Pyrazoline Vinyl ether Medicinal chemistry chemistry.chemical_compound chemistry medicine Organic chemistry medicine.drug
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :1187
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19730001187
Popis:	Norbornadiene, dimethyl acetylenedicarboxylate, and vinyl ethers react with the sulphenic acids produced by heating penicillin S-oxides. Norbornadiene, diketen (4-methyleneoxetan-2-one), and dimethyl acetylenedicarboxylate react by addition, whereas vinyl ethers, such as dihydropyran, react by substitution with loss of water. Methanolysis of the vinyl ether products can be achieved with dilute methanolic hydrochloric acid. Removal of the nitrogen-containing substituent of the β-lactam ring from the vinyl ether products has been effected via the pyrazoline route. A novel substitution reaction occurs on heating the 3-hydroxypenam (22) with acrylaldehyde : methacrylaldehyde is displaced and the 4-hydroxycepham (25) is formed. Some reactions of this cepham are reported.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::73d9179789994dabf5d6303f9a69717a https://doi.org/10.1039/p19730001187 Zobrazit plný text záznamu