Syntheses based on 1,2-secopenicillins. Part III. Hydration of 4-(3-substituted prop-2-ynylthio)azetidin-2-ones and a new cephalosporin synthesis

Autor:	Michael J. Pearson, Neal F. Osborne, Robert Southgate, John H. C. Nayler
Rok vydání:	1976
Předmět:	medicine.drug_class Chemistry Isostere Cephalosporin Ring (chemistry) Triple bond Combinatorial chemistry Hydrolysis Intramolecular force Wittig reaction medicine Cephaloridine Organic chemistry medicine.drug
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :1615
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19760001615
Popis:	Addition of secondary amines to the triple bond of 4-(3-substituted prop-2-ynylthio)azetidin-2-ones or the derived sulphoxides, followed by very ready hydrolysis of the resulting enamines, provides a convenient route to the corresponding β-oxo-sulphides and -sulphoxides. Generation of the carbonyl group in this way, followed by an intramolecular Wittig reaction to close the dihydrothiazine ring, leads to a new synthesis of cephalosporins, illustrated by the preparation of an antibacterially active isostere of cephaloridine.
Databáze:	OpenAIRE
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