Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 19, Pages 7841-7844Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo8014984
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Funding
- National Natural Science Foundation of China [20672065]
- Chinese 863 Project [2007AA02Z160]
- Programs for New Century Excellent Talents in University [NCET-05-0062]
- Changjiang Scholars and innovative Research Team in University (PCSIRT) in China [IRT0404]
- Key Subject Foundation from Beijing Department of Education [XK100030514]
- Beijing City Education Committee [KM20061000 5029]
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We have developed an efficient method for the synthesis of benzimidazoles via cascade reactions of o-haloacetoanilide derivatives with amidine hydrochlorides. The protocol uses 10 mol % CuBr as the catalyst, CS2CO3 as the base, and DMSO as the solvent, and no ligand is required. The procedure proceeds via the sequential coupling of o-haloacetoanilide derivatives with amidines, hydrolysis of the intermediates (amides), and intramolecular cyclization with the loss of NH3 to give 2-substituted 1H-benzimidazoles.
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