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Catalyst-free [3 + 2] cyclization of dihydroisoquinoline imines and isatin-derived Morita–Baylis–Hillman carbonates via 1,5-electrocyclization: synthesis of tetrahydroisoquinoline-fused spirooxindoles

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Abstract

We have developed a mild and scalable catalyst-free [3 + 2] cyclization of dihydroisoquinolines and isatin-derived Morita–Baylis–Hillman carbonates. The incorporation of tetrahydroisoquinoline and spirooxindole frameworks could be realized affording highly functionalized heterocycles in moderate to excellent yields with good diastereocontrols (up to 92% yields, >20 : 1 dr). The extension of this method to dihydro-β-carbolines has also been achieved. A gram-scale reaction could be performed successfully enabling the potential application for further biomedical research.

Graphical abstract: Catalyst-free [3 + 2] cyclization of dihydroisoquinoline imines and isatin-derived Morita–Baylis–Hillman carbonates via 1,5-electrocyclization: synthesis of tetrahydroisoquinoline-fused spirooxindoles

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Publication details

The article was received on 30 Mar 2018, accepted on 17 Apr 2018 and first published on 17 Apr 2018


Article type: Communication
DOI: 10.1039/C8OB00749G
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Catalyst-free [3 + 2] cyclization of dihydroisoquinoline imines and isatin-derived Morita–Baylis–Hillman carbonates via 1,5-electrocyclization: synthesis of tetrahydroisoquinoline-fused spirooxindoles

    X. Tang, Y. Gao, H. Deng, J. Lei, S. Liu, L. Zhou, Y. Shi, H. Liang, J. Qiao, L. Guo, B. Han and H. Cui, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00749G

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