Synthesis 2015; 47(19): 3036-3042
DOI: 10.1055/s-0034-1380447
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Oxa-aza- and Bis-oxathiaaza[3.3.3]propellanes from Dicyanomethylene-1,3-indanedione and 2,5-Dithiobiureas

Alaa A. Hassan*
a   Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, A. R. of Egypt
,
Nasr K. Mohamed
a   Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, A. R. of Egypt
,
Maysa M. Makhlouf
a   Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, A. R. of Egypt
,
Stefan Bräse
b   Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
,
Martin Nieger
c   Laboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki, P.O. Box 55 (A. I. Virtasen aukio I), 00014 Helsinki, Finland   Email: alaahassan2001@mu.edu.eg
› Author Affiliations
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.

Supporting Information

 
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