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Struktur des Hydrazinolyseproduktes von N-(3-Oxo-1-isoindolinyliden)alanin-äthylester


Chaloupka, Stanislav; Bieri, Jost H; Heimgartner, Heinz (1980). Struktur des Hydrazinolyseproduktes von N-(3-Oxo-1-isoindolinyliden)alanin-äthylester. Helvetica Chimica Acta, 63(7):1797-1804.

Abstract

Hydrazinolysis of N-(3-Oxo-1-isoindolinyliden)alanin Ethyl Ester, Structure of the Product
Treatment of N-(3-oxo-1-isoindolinyliden)alanin ethyl ester (6) with hydrazine hydrate leads to 4-methyl-2,3,4,6-tetrahydro[1,2,4]triazino[3,4-a]isoindole-3,6-dione (8, Scheme 3) and not to the previously postulated 6-hydroxy-2-methyl-2,3-dihydroimidazo [2,1-a]phthalazin-3-one (7, cf. [2]). The structure of 8 has been established by an independent synthesis as well as by the X-ray analysis of the reaction product 11 from 8 and 3-dimethylamino-2,2-dimethyl-2H-azirine (1, Scheme 4). A reaction mechanism for the formation of 8 from 6 is suggested in Scheme 5.

Abstract

Hydrazinolysis of N-(3-Oxo-1-isoindolinyliden)alanin Ethyl Ester, Structure of the Product
Treatment of N-(3-oxo-1-isoindolinyliden)alanin ethyl ester (6) with hydrazine hydrate leads to 4-methyl-2,3,4,6-tetrahydro[1,2,4]triazino[3,4-a]isoindole-3,6-dione (8, Scheme 3) and not to the previously postulated 6-hydroxy-2-methyl-2,3-dihydroimidazo [2,1-a]phthalazin-3-one (7, cf. [2]). The structure of 8 has been established by an independent synthesis as well as by the X-ray analysis of the reaction product 11 from 8 and 3-dimethylamino-2,2-dimethyl-2H-azirine (1, Scheme 4). A reaction mechanism for the formation of 8 from 6 is suggested in Scheme 5.

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Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1980
Deposited On:29 Jul 2014 11:03
Last Modified:05 Apr 2016 17:59
Publisher:Wiley-Blackwell
ISSN:0018-019X
Publisher DOI:https://doi.org/10.1002/hlca.19800630707

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