Access to Benzoxazepines and Fully Substituted Indoles via HDDA Coupling
Xiaojie Zheng, Baohua Liu, Feihu Yang, Qiong Hu, Liangliang Yao, Yimin Hu
Abstract
The HDDA-derived benzyne intermediate was captured by oxazolines based on the addition reaction of benzyne to the C═N double bond. Benzoxazepine derivatives, fused benzoxazepine derivatives, and fully substituted indoles are synthesized in one step. The reaction does not require any catalyst or additives. Possible reaction mechanisms are presented.
Topics & Concepts
AryneChemistryCatalysisCombinatorial chemistryCoupling reactionReaction conditionsCoupling (piping)Computational chemistryMedicinal chemistryOrganic chemistryEngineeringMechanical engineeringCyclization and Aryne ChemistrySynthesis and pharmacology of benzodiazepine derivativesBioactive Compounds and Antitumor Agents