A solid phase traceless synthesis of 2-arylaminobenzimidazoles

Authors
Krchnak, V Smith, J Vagner, J
Citation
V. Krchnak et al., A solid phase traceless synthesis of 2-arylaminobenzimidazoles, TETRAHEDR L, 42(9), 2001, pp. 1627-1630
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
9
Year of publication
2001
Pages
1627 - 1630
Database
ISI
SICI code
0040-4039(20010226)42:9<1627:ASPTSO>2.0.ZU;2-1
Abstract
A solid phase traceless synthesis of 2-arylaminobenzimidazoles in three com binatorial steps is reported that is based on acid lability of N-benzylanil ines. MBHA resin was reacted with o-nitrobenzenes, the nitro group was redu ced by tin(II) chloride, the resin-bound o-phenylene diamine was treated wi th isothiocyanates, and the resulting thiourea cyclized by carbodiimide. 2- Arylaminobenzimidazoles were further derivatized with alkyl halides. Target compounds were cleaved from the solid support by TFA or gaseous HF. (C) 20 01 Elsevier Science Ltd. AII rights reserved.