Heterocyclic Communications p. 469 - 472 (2008)
Update date:2022-09-26
Topics:
Basha, N. Jeelan
Reddy, Ch. Upendar
Goudgaon
1-(2-Benzylthiopyrimiden-4-yl)-2-substituted benzimidazoles 6a-d were prepared efficiently in four steps. Reaction of 2-thiouracil with benzyl chloride in presence of base, furnishes 2-benzylthiouracil 2. This on chlorination with excess POCl3 furnishes 4-chloro-2- benzylthiopyrimidine 3. Compound 3 on reaction with ortho-phenylenediamine via aromatic nucleophilic displacement reaction yielded 4-(2-aminoanilino)-2- benzylthiopyrimidine 4. This on cyclization with CS2 in presence of base furnishes 1-(2-benzylthiopyrimidin-4-yl)-2-thiobenzimidazole 5. Compound 5 on reaction with alkyl, aryl halides and hydrazine hydrate yielded target compounds 6a-d in 52-62% yield.
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