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Eine einfache Synthese von 2-Oxazolin-5-onen und verwandten Verbindungen via Amidcyclisierung


Obrecht, Daniel; Heimgartner, Heinz (1982). Eine einfache Synthese von 2-Oxazolin-5-onen und verwandten Verbindungen via Amidcyclisierung. CHIMIA International Journal for Chemistry, 36(2):78-81.

Abstract

A convenient synthesis of 2-oxazolin-5-ones and related compounds via amide cyclization
Acid catalyzed cyclization of diamides 3 leads to 2-oxazolin-5-ones of type 2 in high yield (Scheme 2). Resolution of racemic oxazolinone 2b is accomplished by reaction with (S)-phenylalanin dimethylamide ((S)-5) to yield a diastereomeric mixture of triamides 6 (Scheme 3) and cleavage of the diastereomers with HCl in toluene (cf. also Scheme 4). In an analogous reaction, monothio- and dithio-diamides 10, 12 and 14 have been cyclized to 2-thiazolin-5-ones 11, 2-thiazolin-5-thiones 13, and 2-oxazolin-5-thiones 15, respectively (Schemes 5 and 6).

Abstract

A convenient synthesis of 2-oxazolin-5-ones and related compounds via amide cyclization
Acid catalyzed cyclization of diamides 3 leads to 2-oxazolin-5-ones of type 2 in high yield (Scheme 2). Resolution of racemic oxazolinone 2b is accomplished by reaction with (S)-phenylalanin dimethylamide ((S)-5) to yield a diastereomeric mixture of triamides 6 (Scheme 3) and cleavage of the diastereomers with HCl in toluene (cf. also Scheme 4). In an analogous reaction, monothio- and dithio-diamides 10, 12 and 14 have been cyclized to 2-thiazolin-5-ones 11, 2-thiazolin-5-thiones 13, and 2-oxazolin-5-thiones 15, respectively (Schemes 5 and 6).

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1982
Deposited On:30 Jul 2014 15:01
Last Modified:08 Dec 2017 06:42
Publisher:Swiss Chemical Society
ISSN:0009-4293
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche & Co. AG, Basel
Official URL:https://chimia.ch

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