A [4+3] Annulation Reaction of aza-o-Quinone Methides with Arylcarbohydrazonoyl Chlorides for Synthesis of 2,3-Dihydro-1H-benzo[e][1,2,4]triazepines

作者：Guo, Zhenyan; Jia, Hao; Liu, Honglei; Wang, Qijun; Huang, Jiaxing; Guo, Hongchao^*

来源：Organic Letters, 2018, 20(10): 2939-2943.

DOI：10.1021/acs.orglett.8b00990

• C,N-CYCLIC AZOMETHINE IMINES
• DIELS-ALDER REACTION
• ASYMMETRIC 1,3-DIPOLAR CYCLOADDITIONS
• ENANTIOSELECTIVE 3+3 CYCLOADDITION
• BAYLIS-HILLMAN CARBONATES
• CCK2 RECEPTOR ANTAGONISTS
• N-(ORTHO-CHLOROMETHYL)ARYL AMIDES
• PHTHALAZINIUM DICYANOMETHANIDES
• ACID CATALYSIS
• ACTIVATION STRATEGY

An unprecedented [4 + 3] annulation reaction of aza-ortho-quinone methides with arylcarbohydrazonoyl chlorides has been achieved under mild conditions. The annulation underwent a sequential conjugate addition/intramolecular annulation/rearrangement, providing a useful method for the synthesis of biologically interesting 2,3-dihydro-1H-benzo[e]-[1,2,4] triazepine.

• 出版日期2018-5-18
• 单位中国农业大学