Premium
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
Author(s) -
Park Joon Bum,
Kim Ja Hong,
Zong Kyukwan
Publication year - 2011
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.676
Subject(s) - chemistry , pyrrole , yield (engineering) , medicinal chemistry , combinatorial chemistry , organic chemistry , metallurgy , materials science
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).