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New selenosemicarbazides derived from imidazole-based carbohydrazides


Pieczonka, Adam M; Ciepielowski, Krzysztof; Cebulska, Zofia; Mloston, Grzegorz; Linden, Anthony; Heimgartner, Heinz (2013). New selenosemicarbazides derived from imidazole-based carbohydrazides. Helvetica Chimica Acta, 96(3):397-407.

Abstract

Imidazole-based carbohydrazides, i.e., 3-oxidoimidazole-4-carbohydrazides 1 and 2-[(imidazol-2-yl)sulfanyl]acetohydrazides 6, react with aryl isoselenocyanates 4 in MeOH at room temperature to give the corresponding selenosemicarbazides 5 and 7, respectively, in good yields. On heating 7b in DMF in the presence of air to 100°, 1,3,4-oxadiazole 8a was formed via cyclization and formal elimination of H2Se. Product 8a was also obtained after heating of a mixture of 4a and 6b under the same conditions. On the other hand, on heating of a solution of 7c in MeOH at reflux, a cyclization occurred to give the corresponding 1,2,4-triazole-3-selone 9b. Again, the same product was formed when a mixture of 4b and 6b was heated in MeOH. Surprisingly, analogous cyclizations of selenosemicarbazides of type 5 under the same conditions failed, and only decomposition was observed. The structures of 7a, 7d, and 9b have been established by X-ray crystallography.

Abstract

Imidazole-based carbohydrazides, i.e., 3-oxidoimidazole-4-carbohydrazides 1 and 2-[(imidazol-2-yl)sulfanyl]acetohydrazides 6, react with aryl isoselenocyanates 4 in MeOH at room temperature to give the corresponding selenosemicarbazides 5 and 7, respectively, in good yields. On heating 7b in DMF in the presence of air to 100°, 1,3,4-oxadiazole 8a was formed via cyclization and formal elimination of H2Se. Product 8a was also obtained after heating of a mixture of 4a and 6b under the same conditions. On the other hand, on heating of a solution of 7c in MeOH at reflux, a cyclization occurred to give the corresponding 1,2,4-triazole-3-selone 9b. Again, the same product was formed when a mixture of 4b and 6b was heated in MeOH. Surprisingly, analogous cyclizations of selenosemicarbazides of type 5 under the same conditions failed, and only decomposition was observed. The structures of 7a, 7d, and 9b have been established by X-ray crystallography.

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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:English
Date:March 2013
Deposited On:15 Mar 2013 11:07
Last Modified:07 Dec 2017 20:47
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:European Social Fund 'HUMAN – BEST INVESTMENT!'
Publisher DOI:https://doi.org/10.1002/hlca.201200620

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