Copper-catalyzed, one-pot, three-component synthesis of benzimidazoles by condensation and C-N bond formation.
Benzimidazoles were synthesized by the copper-catalyzed, one-pot, three-component reaction of 2-haloanilines, aldehydes, and NaN(3). The reaction was optimized when 2-iodo- or 2-bromoanilines (1.0 equiv), aldehydes (1.2 equiv), NaN(3) (2.0 equiv), 5 mol% of CuCl, and 5 mol % of TMEDA were reacted in DMSO at 120 °C for 12 h. Good yields resulted, and the reaction showed tolerance toward functional groups such as ester, nitro, and chloro. Aliphatic and heteroaromatic aldehydes also afforded the desired products in moderate to good yields.
Department of Chemistry, Institute of Basic Science, Chonnam National University, 300 Yongbong-dong, Buk-gu, Gwangju 500-757, Republic of Korea.
Yong
Y
Kim
Manian Rajesh
MR
Kumar
Namjin
N
Park
Yumi
Y
Heo
Sunwoo
S
Lee
D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D001562:Benzimidazoles; D009942:Organometallic Compounds; D003300:Copper