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Paper | Regular issue | Vol 36, No. 10, 1993, pp.2335-2344
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6463
Application of the Photo-Fries Rearrangement of Aryl N-Chloroacetylanthranylates as Key Step in the Synthesis of 5-(2-Hydroxyphenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-ones

Felipe Algarra and Miguel A. Miranda*

*Departamento de Química/Instituto de Tecnología Química, UPV-CSIC, Universidad Politécnica de Valencia, Apartado 22012, E-46071 Valencia, Spain

Abstract

Condensation of isatoic anhydride with phenols, followed by treatment of the resulting aryl anthranylates (4) with chloroacetyl chloride gives aryl N-chloroacetylanthranylates (5). Their uv-irradiation results in photo-Fries rearrangement, to afford benzophenones (6). Direct treatment of the latter with ammonia gives rise to 1,3-quinazolines (7); by contrast, treatment of 6 with potassium iodide and subsequently with ammonia leads to 1,3-dihydro-2H-1,4-benzodiazepin-2-ones (1).