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Umsetzung von 3-(Dimethylamino)-2H-azirinen mit 1,3-Oxazolidin-2-thion zu 3-(2-Hydroxyethyl)-2-thiohydantoinen


Ametamey, Simon M; Heimgartner, Heinz (1990). Umsetzung von 3-(Dimethylamino)-2H-azirinen mit 1,3-Oxazolidin-2-thion zu 3-(2-Hydroxyethyl)-2-thiohydantoinen. Helvetica Chimica Acta, 73(3):594-598.

Abstract

The reaction of 3-(dimethylamino)-2H-azirines 1 and 1,3-oxazolidine-2-thione (6), in MeCN at room temperature, yields, after hydrolytic workup, 3-(2-hydroxyethyl)-2-thiohydantoins 7 (Scheme 2). In the case of the spirocyclic 1c , crystallization of the crude reaction mixture leads to spiro[cyclopentane-l,7'(7'aH)-imidazo[4.3-b]oxazole]-5'-thione 8c. The mechanism is discussed.

Abstract

The reaction of 3-(dimethylamino)-2H-azirines 1 and 1,3-oxazolidine-2-thione (6), in MeCN at room temperature, yields, after hydrolytic workup, 3-(2-hydroxyethyl)-2-thiohydantoins 7 (Scheme 2). In the case of the spirocyclic 1c , crystallization of the crude reaction mixture leads to spiro[cyclopentane-l,7'(7'aH)-imidazo[4.3-b]oxazole]-5'-thione 8c. The mechanism is discussed.

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Other titles:Reaction of 3-(Dimethylamino)-2H-azirines with 1,3-Oxazolidine-2-thione to 3-(2-Hydroxyethyl)-2-thiohydantoins
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1990
Deposited On:27 Mar 2014 15:34
Last Modified:05 Apr 2016 17:46
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche AG, Basel, Prof. Hans-E.-Schmid-Stiftung, Anna-Feddersen-Wagner-Fonds
Publisher DOI:https://doi.org/10.1002/hlca.19900730307

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