Collect. Czech. Chem. Commun.
2003, 68, 1243-1263
https://doi.org/10.1135/cccc20031243
Syntheses and Structure Study on 3,3aλ4,4-Trithia-1-azapentalenes and Their 3-Oxa Analogues
Richard Čmelíka, Michal Čajanb, Jaromír Marekc and Pavel Pazderaa,*
a Department of Organic Chemistry, Faculty of Science, Masaryk University, Kotlářská 2, CZ-611 37 Brno, Czech Republic
b National Centre for Biomolecular Research, Faculty of Science, Masaryk University, Kotlářská 2, CZ-611 37 Brno, Czech Republic
c Laboratory of Functional Genomics and Proteomics, Masaryk University, Kotlářská 2, CZ-611 37 Brno, Czech Republic
Abstract
Reactions of nitrile, amide or ester of 5-amino-3-thioxo-3H-1,2-dithiole-4-carboxylic acid 1 with alkylation and acylation agents were studied. "Ionic" 1,2-dithiole amides 6 were formed in several ways. Treatment with phosphorus pentasulfide afforded the corresponding 3,3aλ4,4-trithia-1-azapentalenes 7. Structures of the synthesized heterocycles were studied using a combination of X-ray analysis, IR spectroscopy, and HF and DFT quantum-chemical calculations.
Keywords: Acylations; Alkylations; DFT calculation; Sulfur heterocycles; Trithiapentalenes; X-Ray diffraction; Disulfides; Cyclizations.
References: 22 live references.
