Adepu, Raju ; Dhanaji, Jadhav Rahul ; Samatha, Polasani ; Mainkar, Prathama S. ; Chandrasekhar, Srivari (2020) Synthesis of 2-Amino-2′-hydroxy-1,1′-biaryls via Cascade Benzannulation and C–N Bond Cleavage Sequence Organic Letters, 22 (21). pp. 8224-8228. ISSN 1523-7060
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Official URL: http://doi.org/10.1021/acs.orglett.0c02749
Related URL: http://dx.doi.org/10.1021/acs.orglett.0c02749
Abstract
A serendipitous synthesis of N-substituted 2-amino-2′-hydroxy-1,1′-biaryls through an aryne annulation with indolyl β-ketonitrile/ester in a cascade manner is demonstrated. The reaction sequence involves benzyne-mediated [2 + 2] Stoltz-type cycloaddition–cleavage and intramolecular Michael addition followed by C–N bond cleavage under transition-metal-free reaction conditions. Interestingly, while [4 + 2] Diels–Alder reaction is a possible pathway, no traces of the regioisomer was isolated.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society |
| ID Code: | 131271 |
| Deposited On: | 06 Dec 2022 08:44 |
| Last Modified: | 06 Dec 2022 08:44 |
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