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[4+2]‐Cycloaddition of para ‐Quinone Methides with Hexahydro‐1,3,5‐Triazines: Access to 1,3‐Benzoxazine Derivatives
Author(s) -
Cheng Xiao,
Zhou ShuangJing,
Xu GuoYong,
Wang Long,
Yang QingQing,
Xuan Jun
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901169
Subject(s) - chemistry , cycloaddition , quinone , combinatorial chemistry , substrate (aquarium) , functional group , catalysis , ligand (biochemistry) , scope (computer science) , surface modification , base (topology) , organic chemistry , receptor , mathematical analysis , biochemistry , oceanography , polymer , mathematics , computer science , programming language , geology
A [4+2]‐cycloaddition of para ‐quinone methides with hexahydro‐1,3,5‐triazines is reported. The reaction occurs under very mild conditions (catalyst‐, ligand‐, and base‐free), exhibits a broad substrate scope and excellent functional group tolerance, and affords a series of biologically important 1,3‐benzoxazine derivatives in good to excellent yields. Moreover, the successful late‐stage functionalization of pharmaceutically relevant compounds further renders the approach valuable.