‘One-pot’ nitro reduction–cyclisation solid phase route to benzimidazoles

作者: Zemin Wu , Philip Rea , Geoffrey Wickham

DOI: 10.1016/S0040-4039(00)01732-9

关键词: BenzimidazoleSolid-phase synthesisNitro reductionChemistryOrganic chemistry

摘要: An improved solid phase synthesis of benzimidazoles is described. A polymer-bound o-nitroaniline was reacted with aldehydes in DMF the presence SnCl2·2H2O at 60°C for three hours to give excellent purity and good yield after TFA cleavage. library 25 prepared using this ‘one-pot’ procedure.

参考文章(14)
Jung Lee, Diane Gauthier, Ralph A. Rivero, Solid phase synthesis of 1-alkyl-2-alkylthio-5-carbamoylbenzimidazoles Tetrahedron Letters. ,vol. 39, pp. 201- 204 ,(1998) , 10.1016/S0040-4039(97)10525-1
Jennifer M. Smith, Viktor Krchňák, A solid phase traceless synthesis of benzimidazoles with three combinatorial steps Tetrahedron Letters. ,vol. 40, pp. 7633- 7636 ,(1999) , 10.1016/S0040-4039(99)01560-9
David Tumelty, Matthias K. Schwarz, Kathy Cao, Michael C. Needels, Solid-phase synthesis of substituted benzimidazoles Tetrahedron Letters. ,vol. 40, pp. 6185- 6188 ,(1999) , 10.1016/S0040-4039(99)01299-X
Wolin Huang, Robert M. Scarborough, A new “traceless” solid-phase synthesis strategy: Synthesis of a benzimidazole library Tetrahedron Letters. ,vol. 40, pp. 2665- 2668 ,(1999) , 10.1016/S0040-4039(99)00293-2
Qun Sun, Bing Yan, Single bead ir monitoring of a novel benzimidazole synthesis Bioorganic & Medicinal Chemistry Letters. ,vol. 8, pp. 361- 364 ,(1998) , 10.1016/S0960-894X(98)00024-9
David Tumelty, Matthias K. Schwarz, Michael C. Needels, Solid-phase synthesis of substituted 1-phenyl-2-aminomethyl-benzimidazoles and 1-phenyl-2-thiomethyl-benzimidazoles Tetrahedron Letters. ,vol. 39, pp. 7467- 7470 ,(1998) , 10.1016/S0040-4039(98)01672-4
Jennifer M. Smith, Jaime Gard, Wendy Cummings, Angelika Kanizsai, Viktor Krchňák, Necklace-Coded Polymer-Supported Combinatorial Synthesis of 2-Arylaminobenzimidazoles ACS Combinatorial Science. ,vol. 1, pp. 368- 370 ,(1999) , 10.1021/CC9900201
Gary B. Phillips, Guo Ping Wei, Solid phase synthesis of benzimidazoles Tetrahedron Letters. ,vol. 37, pp. 4887- 4890 ,(1996) , 10.1016/0040-4039(96)01002-7
Pi-Chi Pan, Chung-Ming Sun, High-throughput combinatorial synthesis of substituted benzimidazolones Tetrahedron Letters. ,vol. 40, pp. 6443- 6446 ,(1999) , 10.1016/S0040-4039(99)01276-9
Guillermo A. Morales, Jeffrey W. Corbett, William F. DeGrado, Solid-Phase Synthesis of Benzopiperazinones Journal of Organic Chemistry. ,vol. 63, pp. 1172- 1177 ,(1998) , 10.1021/JO971688+