SYNTHESIS OF 1-ALKOXY-2-ALKYL-BENZIMIDAZOLES FROM 2-NITROANILINES VIATANDEM N-ALKYLATION-CYCLIZATION-O-ALKYLATION

Authors
GARDINER JM LOYNS CR SCHWALBE CH BARRETT GC LOWE PR
Citation
Jm. Gardiner et al., SYNTHESIS OF 1-ALKOXY-2-ALKYL-BENZIMIDAZOLES FROM 2-NITROANILINES VIATANDEM N-ALKYLATION-CYCLIZATION-O-ALKYLATION, Tetrahedron, 51(14), 1995, pp. 4101-4110
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
14
Year of publication
1995
Pages
4101 - 4110
Database
ISI
SICI code
0040-4020(1995)51:14<4101:SO1F2V>2.0.ZU;2-1
Abstract
Substituted 2-nitroanilines react with benzylic, allyl and alkyl halid es to give 2-aryl-1-benzyloxy-, 1-allyloxy-2-vinyl- and 1-alkoxy-2-alk yl-benzimidazoles, in a one-pot cascade process involving 1-alkylation -cyclization-O-alkylation. 2-Aryl-1-benzyloxy- and 1-allyloxy-2-vinyl- derivatives are obtained in high yields (79-98%), while with simple a lkyl halides, yields of the benzimidazoles are substrate dependent. An X-ray crystal structure of 2,4-dimethyl-1-ethoxybenzimidazole is pres ented.