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Synthese von 1, 3, 4-Oxadiazolen und 4, 5-Dihydro-1, 2, 4-triazinen aus 3-Dimethylamino-2, 2-dimethyl-2 H-azirin und Carbohydraziden

✍ Scribed by Helmut Link

Publisher
John Wiley and Sons
Year
1978
Tongue
German
Weight
551 KB
Volume
61
Category
Article
ISSN
0018-019X

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✦ Synopsis

Synthesis of 1,3,4‐Oxadiazoles and 4,5‐Dihydro‐l,2,4‐triazines from 3‐Dimethylamino‐2,2‐dimethyl‐2 __H__azirine and Carbohydrazides

3‐Dimethylamino‐2, 2‐dimethyl‐2 H‐azirine (1) reacts with aromatic carbohydrazides to give 2‐(1‐amino‐1‐methylethyl)‐5‐aryl‐1, 3, 4‐oxadiazoles (7, 10, 11). With ethyl carbazate the azirine 1 forms the aminoester 15, which is easily cyclized to the 4, 5‐dihydro‐1, 2, 4‐triazin‐3 (2__H__)‐one 16. From the reaction of 1 with oxamohydrazide (17) and oxalodihydrazide 19 the 4, 5‐dihydro‐1, 2, 4‐triazin‐3‐carboxamide 18 and the symmetric compound 20, respectively, have been isolated. Reactions supporting the structures of the new compounds are described.

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