Dicarboxylic Acid Monoesters in β- and δ-Lactam Synthesis

Autor:	Anna Ananeva, Olga Bakulina, Dmitry Dar’in, Grigory Kantin, Mikhail Krasavin
Jazyk:	angličtina
Rok vydání:	2022
Předmět:	beta-lactams delta-lactams regioselectivity imines carboxylic acid activation cyclization Organic chemistry QD241-441
Zdroj:	Molecules, Vol 27, Iss 8, p 2469 (2022)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules27082469
Popis:	A N-(2-methoxy-2-oxoethyl)-N-(phenylsulfonyl)glycine monomethyl ester of the respective dicarboxylic acid was involved in a reaction with imines promoted by acetic anhydride at an elevated temperature. Instead of the initially expected δ-lactam products of the Castagnoli–Cushman-type reaction, medicinally important 3-amino-2-azetidinones were obtained as the result of cyclization, involving a methylene group adjacent to an acid moiety. In contrast, replacing alcohol residue with hexafluoroisopropyl in the same substrate made another methylene group (adjacent to the ester moiety) more reactive to furnishing the desired δ-lactam in the Castagnoli–Cushman fashion.
Databáze:	Directory of Open Access Journals
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