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Synthesis 2015; 47(19): 3036-3042
DOI: 10.1055/s-0034-1380447
DOI: 10.1055/s-0034-1380447
paper
Synthesis of Oxa-aza- and Bis-oxathiaaza[3.3.3]propellanes from Dicyanomethylene-1,3-indanedione and 2,5-Dithiobiureas
Further Information
Publication History
Received: 17 March 2015
Accepted after revision: 06 May 2015
Publication Date:
07 July 2015 (online)
Abstract
An efficient route for the synthesis of oxa-aza- and bis-oxathiaaza[3.3.3]propellanes via reactions of symmetrical and unsymmetrical N1,N2-disubstituted hydrazine-1,2-dicarbothioamides (2,5-dithiobiureas) with (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile in tetrahydrofuran is described. The rationale behind these conversions involving nucleophilic addition on the dicyanomethylene carbon atom is presented. The structures of these unusual products are confirmed by X-ray crystal structure analysis.
Key words
dicyanomethylene-1,3-indanedione - 2,5-dithiobiureas - oxa-aza[3.3.3]propellane - bis-oxathiaaza[3.3.3]propellanes - N2,N5-disubstituted 1,3,4-thiadiazolesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-34-1380447.
- Supporting Information
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