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A convenient synthesis of pyrrolo-annelated 1,3-diselenole-2-thione and 1,3-diselenol-2-one derivatives via dipyrrolo-annelated 1,2,5,6-tetraselenocine derivatives

✍ Scribed by Joon Bum Park; Ja Hong Kim; Kyukwan Zong

Publisher: Journal of Heterocyclic Chemistry
Year: 2011
Tongue: English
Weight: 202 KB
Volume: 48
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.676

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✦ Synopsis

Abstract

The reaction of 2,5‐dimethyl‐3,4‐diselenocyanato‐1__H__‐pyrrole by NaBH~4~ or NaOCH~3~ led to tetraselenide 7 in quantitative yield. Treatment of protected tetraselenide 8 with LiAlH~4~ afforded the aluminum complex intermediate that was converted into pyrrole‐annelated 1,3‐diselenolo‐2‐thione 9 in excellent yield. Similarly, treatment of tetraselenide 8 with LiAlH~4~ followed by TFA afforded 1,2‐diselenol intermediate that was converted into pyrrole‐annelated 1,3‐diselenolo‐2‐one 10 upon treatment of diimidazole carbonate. J. Heterocyclic Chem., (2011).

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