ISSN:
1434-4475
Keywords:
Keywords. Fused heterocycles; 4H-Imidazoles; Nucleophilic substitution; 1
;
3
;
5
;
7-Tetraazafulvalenes.
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary. Different reactivities towards the 4H-imidazoles 1 depending on the nature of the sulfur containing nucleophile were observed. Whereas H2S and aromatic thioles led to 4,5-diaminoimidazoles in the course of a reduction process, treatment with aliphatic mercaptanes resulted in a substitution-reduction-dimerization cascade which finally gave bis-imidazoles. Their oxidative modification in presence of m-chloroperbenzoic acid then allowed new 1,3,5,7-tetraazafulvalenes to be easily obtained. Treatment of the bis-imidazoles with acetylene dimethyldicarboxylate caused cleavage of the central bond, thus leading to the formation of derivatives which are of interest for the transformation into fused heterocycles such as imidazo[4,5-b]azepines.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/s007060070026
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