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Strained 1-Azabicyclo[1.1.0]butanes in the synthesis of Azetidinethiocarboxylate derivatives


Woznicka, M; Urbaniak, K; Mloston, G; Heimgartner, H (2006). Strained 1-Azabicyclo[1.1.0]butanes in the synthesis of Azetidinethiocarboxylate derivatives. Heterocycles, 69:351-364.

Abstract

The reaction of 3-phenyl-1-azabicyclo[1.1.0]butane (1a) with chlorodithio-formates (5) at room temperature yielded 3-chloro-3-phenylazetidine-1-carbodithioates (6). The same products were obtained in a two-step procedure by treatment of 1a with thiophosgene to give azetidine-1-carbothioyl chloride (7a), followed by treatment with the corresponding sulfane. 3-Chloro-3-phenylazetidine-1-thiocarbamides (8) and the corresponding O-methyl 1-carbothioates (9) were prepared by the reaction of compounds (7) with amines and methanol, respectively. These reactions open a new access to derivatives of azetidine-1-carboxylic acid.

Abstract

The reaction of 3-phenyl-1-azabicyclo[1.1.0]butane (1a) with chlorodithio-formates (5) at room temperature yielded 3-chloro-3-phenylazetidine-1-carbodithioates (6). The same products were obtained in a two-step procedure by treatment of 1a with thiophosgene to give azetidine-1-carbothioyl chloride (7a), followed by treatment with the corresponding sulfane. 3-Chloro-3-phenylazetidine-1-thiocarbamides (8) and the corresponding O-methyl 1-carbothioates (9) were prepared by the reaction of compounds (7) with amines and methanol, respectively. These reactions open a new access to derivatives of azetidine-1-carboxylic acid.

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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:2006
Deposited On:25 Nov 2011 10:20
Last Modified:05 Apr 2016 15:07
Publisher:Elsevier
ISSN:0385-5414
Funders:Polish State Committee for Scientific Research (grant 4T09A04625)), F. Hoffmann-La Roche AG, Basel

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