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Electrochemical synthesis of heterocyclic compounds—XIII. (1) Anodic synthesis of 1, 3-imidazoles and 1, 3-oxazoles derivatives

✍ Scribed by M. Laćan; V. Rogić; I. Tabaković; D. Galijaš; T. Solomun

Publisher
Elsevier Science
Year
1983
Tongue
English
Weight
754 KB
Volume
28
Category
Article
ISSN
0013-4686

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✦ Synopsis

Anodic oxidation of a series of structurally different Schiff bases (la-ISa), prepared from +phenylendiamine, o-aminophenol, 3-amino-4-hydroxycoumarine or 3, Cdiaminoco-rine and corresponding aromatic aldehyde, were performed in acetonitrile-tetraethylammonium perchlorate electrolyte solution at platinum using controlled potentials. As a result of two-electron oxidative cyclodehydrogenations several 1, Soxazoles derivatives (lb-lob) and 1,3-imidazoles derivatives (1 l&lSb) were prepared in the yields ranging from 60 to 90%. A mechanism rationalizing the formation of 2-anisylbenzimidazole, llb, and 2-anisyibenzoxazole, 3b, has been studied by Isv, cpsv, rde, coulommetry and preparative scale electrolysis.

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