A cascade of acid-promoted C-O bond cleavage and redox reactions: from oxa-bridged benzazepines to benzazepinones.

Yuewei Zhang, Fengzhi Yang, Lianyou Zheng, Qun Dang, Xu Bai

Organic letters 2014 Dec 5

filter terms:

A sequence of C-O bond cleavage and redox reactions in oxa-bridged azepines was realized under acid promoted conditions. This protocol provides an atom-economical and straightforward approach to access benzo[b]azepin-5(2H)-ones in high yields. The formal synthesis of tolvaptan was achieved by exploiting this new transformation.

Citation

Yuewei Zhang, Fengzhi Yang, Lianyou Zheng, Qun Dang, Xu Bai. A cascade of acid-promoted C-O bond cleavage and redox reactions: from oxa-bridged benzazepines to benzazepinones. Organic letters. 2014 Dec 5;16(23):6041-3