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Synthesis of 1‐Substituted Benzimidazoles from o ‐Bromophenyl Isocyanide and Amines
Author(s) -
Lygin Alexander V.,
de Meijere Armin
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900820
Subject(s) - chemistry , isocyanide , primary (astronomy) , medicinal chemistry , catalysis , organic chemistry , physics , astronomy
o ‐Bromophenyl isocyanide ( 1 ‐Br) reacts with various primary amines under Cu I catalysis to afford 1‐substituted benzimidazoles 4 in moderate to good yields (38–70 %, 13 examples). Analogously, 2‐bromo‐3‐isocyanothiophene ( 6 ) furnishes 3‐substituted 3 H ‐thieno[2,3‐ d ]imidazoles 7 (44–49 %, 3 examples). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)