Das, Tamal Kanti ; Madica, Krishnaprasad ; Krishnan, Jagadeesh ; Marelli, Udaya Kiran ; Biju, Akkattu T. (2020) N-Heterocyclic Carbene Catalysis Exploiting Oxidative Imine Umpolung for the Generation of Imidoyl Azoliums The Journal of Organic Chemistry, 85 (7). pp. 5114-5121. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/acs.joc.0c00360
Related URL: http://dx.doi.org/10.1021/acs.joc.0c00360
Abstract
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society |
| ID Code: | 128598 |
| Deposited On: | 03 Nov 2022 06:45 |
| Last Modified: | 03 Nov 2022 06:45 |
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