Divergent synthesis of new naphtho-fused 2-aminoindolines and naphthoxindoles based on straightforward construction of phenanthrene

An environmentally friendly, highly atom-economical and operationally simple approach toward the synthesis of naphtho-fused 2-aminoindolines and naphthoxindoles starting from biaryl aldehydes and secondary amines has been developed. This notable methodology integrates consecutive intramolecular Mann...

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Bibliographic Details
Main Authors: Bin Qiu, Ya-Fei Shi, Xiao-De An, Shu-Kui Guo, Yao-Bin Shen, Jian Xiao
Format: Article
Language:English
Published: KeAi Communications Co. Ltd. 2025-02-01
Series:Green Synthesis and Catalysis
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Online Access:http://www.sciencedirect.com/science/article/pii/S2666554923000832
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Summary:An environmentally friendly, highly atom-economical and operationally simple approach toward the synthesis of naphtho-fused 2-aminoindolines and naphthoxindoles starting from biaryl aldehydes and secondary amines has been developed. This notable methodology integrates consecutive intramolecular Mannich-type cyclization triggered by the dearomatization of indole with subsequent aromatization via β-elimination and then amination or oxidation at the C2-position of the indole nucleus. The secondary amine-controlled divergent protocol together with an easy product isolation process provides a practical route for the first time to access naphtho-fused 2-substituted indoline.
ISSN:2666-5549