Nayak, Sanatan ; Ghosh, Nayan ; Prabagar, B. ; Sahoo, Akhila K. (2015) p-TsOH Promoted Au(I)-Catalyzed Consecutive Endo Cyclization of Yne-Tethered Ynamide: Access to Benzofused Dihydroisoquinolones Organic Letters, 17 (22). pp. 5662-5665. ISSN 1523-7060
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Official URL: http://doi.org/10.1021/acs.orglett.5b02946
Related URL: http://dx.doi.org/10.1021/acs.orglett.5b02946
Abstract
A novel synthetic route to benzo[f]dihydroisoquinolone through a p-TsOH promoted cascade cyclization of easily accessible diyne-tethered ynamides in the presence of a Au(I)-catalyst is described. This reaction unveils a broad substrate scope, constructing a wide range of benzo[f]dihydroisoquinolones in good yields. The diyne-tethered ynamides are synthesized from inexpensive o-iodoaniline through Sonogashira couplings and the Cu-mediated C–N bond formation. The role of p-TsOH is examined, and the reaction pathway is also deduced. The benzo[f]isoquinoline scaffold is constructed from benzo[f]dihydroisoquinolones.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 122437 |
| Deposited On: | 02 Aug 2021 13:58 |
| Last Modified: | 02 Aug 2021 13:58 |
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