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Title: Synthesis of N-alkylated-2-(1,3-diphenyl-1H-pyrazol-4-ylsulfanyl)-1H- benzimidazoles by Vilsmeir-Haack reaction and by condensation with DMF-DMA
Authors: Rao, S Srinivas
Mahesh, Putluru
Reddy, Ch Venkata Ramana
Dubey, P K
Keywords: 2-Mercaptobenzimidazole;Phenacyl bromide;K2CO3;TBAB;Pyrazole
Issue Date: Apr-2015
Publisher: NISCAIR-CSIR, India
Abstract: 2-(1H-Benzimidazol-2-ylsulfanyl)-1-phenylethanone 3 on condensation with phenyl hydrazine under acidic conditions gives the corresponding hydrazone derivative which when subjected to Vilsmeir Hack formylation followed by alkylation under phase transfer catalyst (PTC) conditions gives N-alkylated-2-(1,3-diphenyl-1H-pyrazol-4-ylsulfanyl)-1H-benzimidazole 7a-d. Alternatively 7a-d can also be prepared by treatment of 3 with DMF-DMA at RT for 3 hr giving 2-(1H-benzimidazol-2-ylsulfanyl)-3-dimethylamino-1-phenylpropenone 10 followed by condensation with phenyl hydrazine under acidic conditions and subsequent alkylation with an alkylating agent under PTC conditions. Compound 3 itself has been prepared from the well known benzimidazole thiol 1 by condensation with phenacyl bromide 2.
Page(s): 531-537
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.54B(04) [April 2015]

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