Sharma, Rohit ; Abbat, Sheenu ; Mudududdla, Ramesh ; Vishwakarma, Ram A. ; Bharatam, Prasad V. ; Bharate, Sandip B. (2015) ortho -Quinone methides: TFA-mediated generation in water and trapping with lactams and styrenes Tetrahedron Letters, 56 (27). pp. 4057-4059. ISSN 0040-4039
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Official URL: http://doi.org/10.1016/j.tetlet.2015.04.072
Related URL: http://dx.doi.org/10.1016/j.tetlet.2015.04.072
Abstract
A simple and efficient trifluoroacetic acid mediated protocol for ortho-amidomethylation of phenols in aqueous medium has been described. Developed protocol has a good substrate scope, involves mild reaction conditions, and products are obtained in good yields. The quantum chemical calculations were performed in implicit solvent (water) conditions, which helped in tracing the reaction mechanism and getting insights on the possible reaction pathway, which involves the Nsingle bondC bond formation and simultaneous hydrogen transfer to give final product. The applicability of this protocol for one-pot synthesis of flavans from phenols, formaldehyde and styrene has also been demonstrated.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier B.V. |
| Keywords: | DFT; TFA; Vinylbenzenes; Amidomethylation. |
| ID Code: | 116412 |
| Deposited On: | 12 Apr 2021 09:33 |
| Last Modified: | 12 Apr 2021 09:33 |
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