Journal of Organic Chemistry p. 5114 - 5121 (2020)
Update date:2022-08-30
Topics:
Das, Tamal Kanti
Madica, Krishnaprasad
Krishnan, Jagadeesh
Marelli, Udaya Kiran
Biju, Akkattu T.
Although NHC-catalyzed umpolung of imines are known, the related reactions under oxidative conditions are limited. Described herein is the two-step process involving the initial formation of aldimines from the corresponding aldehydes and 2-amino benzyl alcohols followed by NHC-catalyzed cyclization proceeding via the imidoyl azoliums under oxidative conditions. The reaction allowed the synthesis of trifluoromethylated 3,1-benzoxazines in good yields and broad scope. The role of NHC in the intramolecular cyclization and preliminary mechanistic experiments are also provided.
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(2021)