RHC 3288 [1-methyl-2(1,3,4-oxadiazol-2(3H)-one-5-yl) benzimidazole] and related compounds

Khandwala, Atul; Coutts, Stephen M.; Dally-Meade, Vernetta; Jariwala, N.; Musser, John H.; Brown, R. W.; Jones, Howard; Loev, Bernard; Weinryb, Ira

doi:10.1016/0006-2952(83)90358-1

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Cited by 4 publications

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Organocatalytic Enantioselective α‐Amination of Thiazol‐4‐one‐5‐carboxylates with Azodicarboxylates

Wang

Fan

2018

Asian J Org Chem

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An effective method for the asymmetric synthesis of 5-hydrazinothiazol-4-one-5-carboxylates was developed. The tetrasubstituted chiral carbon center was generated by asymmetric amination of thiazol-4-one-5-carboxylate with azodicarboxylate catalyzed by a bifunctional squaramidebased (1R,2R)-cyclohexane-1,2-diamine backbone in good to excellent yields (40-96%) with high levels of enantioselectiv-ity (92-98% ee). A representative transformation of the amination product to a biologically important 1,3,4-oxadiazol-2(3H)-one is achieved without any appreciable loss in enantioselectivity. Additionally, upon treatment with NaBH 3 CN, the amination product could also be converted into a biologically important thiazolidin-4-one derivative in good yield without any loss of stereochemical integrity.

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