Syntheses based on 1,2-secopenicillins. Part 5. Penicillin analogues with electron-withdrawing 2-substituents
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 22,p. 2479-2487
- https://doi.org/10.1039/p19770002479
Abstract
6-Acylaminopenam-3-carboxylic esters substituted at C-2 by one or two alkoxycarbonyl groups or by an acetyl group have been prepared from penicillins. The azetidinone ring remained intact throughout the reaction sequence, and the thiazolidine ring was completed by intramolecular alkylation at an activated methylene or methine group adjacent to the sulphur atom. Only in the case of the 2-alkoxycarbonylpenams could stable carboxylic acids be liberated from the esters.This publication has 5 references indexed in Scilit:
- 1-Oxadethiapenicillins: synthesis and stereochemical assignments using lanthanide induced shiftsJournal of the Chemical Society, Chemical Communications, 1977
- Syntheses based on 1,2-secopenicillins. Part 4. A new tricyclic β-lactam derivativeJournal of the Chemical Society, Perkin Transactions 1, 1976
- Preparation and isomerization of 5-epibenzylpenicillinsThe Journal of Organic Chemistry, 1976
- Syntheses based on 1,2-secopenicillins. Part II. Preparation of 4-(3-substituted prop-2-ynylthio)azetidin-2-onesJournal of the Chemical Society, Perkin Transactions 1, 1976
- Syntheses based on 1,2-secopenicillins. Part I. OxidationJournal of the Chemical Society, Perkin Transactions 1, 1976