gamma-Al2O3/triflic acid as cooperative catalysts for the tandem Michael addition/carbocyclization: an easy access to 2-substituted pyrrolo[2,1-a]isoquinolines and 3-substituted pyrrolidine-2,5-diones
| Title | gamma-Al2O3/triflic acid as cooperative catalysts for the tandem Michael addition/carbocyclization: an easy access to 2-substituted pyrrolo[2,1-a]isoquinolines and 3-substituted pyrrolidine-2,5-diones |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Rao, RSreenivasa, Sahani, A, Ali, SHaider, Pradhan, S, Ramanathan, CRamaraj |
| Journal | Journal of Heterocyclic Chemistry |
| Volume | 58 |
| Issue | 7 |
| Pagination | 1415-1428 |
| Date Published | JUL |
| Type of Article | Article |
| ISSN | 0022-152X |
| Keywords | 1-a]isoquinolines, 3-substituted pyrrolidine-2, 5-diones, carbocyclization, gamma-Al2O3/TfOH binary system, Michael addition, pyrrolo[2 |
| Abstract | A tandem Michael addition/carbocyclization of 3,4-dimethoxyphenethyl maleimide with carbon and sulfur nucleophiles is accomplished via a relay catalysis using gamma-Al2O3/TfOH binary system. The X-ray Photoelectron Spectroscopy (XPS) analysis of binary system indicates the presence of AlF3, AlO(OH) species(.) This approach provides an easy access to 2-aryl or 2-thio aryl pyrrolo[2,1-a]isoquinolines in good yields in a tandem fashion. With suitable ratio of gamma-Al2O3/TfOH binary system, the Michael addition of N/C/S nucleophiles to N-benzyl maleimide is also achieved. A key to the success of these reactions would be the generation of AlF3, AlO(OH) species from gamma-Al2O3 and TfOH, which might have delineated the disadvantageous background reactions usually displayed by a strong Bronsted acid such as TfOH. |
| DOI | 10.1002/jhet.4266, Early Access Date = APR 2021 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.193 |
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