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Reaktionen von 3-Dimethylamino-2,2-dimethyl-2H-azirin mit aromatischen Carbonsäurehydraziden


Chaloupka, Stanislav; Heimgartner, Heinz (1978). Reaktionen von 3-Dimethylamino-2,2-dimethyl-2H-azirin mit aromatischen Carbonsäurehydraziden. CHIMIA International Journal for Chemistry, 32(9):332-333.

Abstract

Reaction of the 3-dimethylamino-2,2-dimethyl-2H-azirine (1) with salicylic acid hydrazide (2c) in acetonitrile at room temperature gives the amidrazone 3a as a primary product in 78% yield. Cyclization of 3c in methanol leads to the 1,2,5,6-tetrahydro-1,2,4-triazin-6-one 4, whereas the cyclization in DMSO gives a mixture of 4 and the 5-dimethylamino-2,4-dihydro-1,2,4-triazine 5. Benzoic acid hydrazides of type 6 react with 1 in acetonitrile at 80 °C to give the 1,3,4-oxadiazoles of type 7 in good yield.

Abstract

Reaction of the 3-dimethylamino-2,2-dimethyl-2H-azirine (1) with salicylic acid hydrazide (2c) in acetonitrile at room temperature gives the amidrazone 3a as a primary product in 78% yield. Cyclization of 3c in methanol leads to the 1,2,5,6-tetrahydro-1,2,4-triazin-6-one 4, whereas the cyclization in DMSO gives a mixture of 4 and the 5-dimethylamino-2,4-dihydro-1,2,4-triazine 5. Benzoic acid hydrazides of type 6 react with 1 in acetonitrile at 80 °C to give the 1,3,4-oxadiazoles of type 7 in good yield.

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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:September 1978
Deposited On:19 Aug 2014 14:15
Last Modified:05 Apr 2016 18:01
Publisher:Swiss Chemical Society
ISSN:0009-4293
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung

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