A novel and efficient iodine(III)-mediated access to 1,4-benzodiazepin-2-ones

✍ Scribed by M.Teresa Herrero; Imanol Tellitu; Esther Domı́nguez; Isabel Moreno; Raúl SanMartı́n

• Book ID: 104252227
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 126 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02019-1

✦ Synopsis

A novel access to 1,4-benzodiazepin-2-ones starting from glycine and alanine derivatives is described. The key cyclization step was performed by the action of phenyliodine(III)bis(trifluoroacetate) (PIFA) on the corresponding methoxyamide derivatives leading to the C(9a) N(1) bond construction. This strategy avoids the necessity of additional functionalization on the phenyl ring and facilitates the access to a number of 1,4-benzodiazepine derivatives. Additionally, no racemization in the cyclization step was observed starting from optically pure (S)-alanine ester.