InCl3‐Driven Regioselective Synthesis of Functionalized/Annulated Quinolines: Scope and Limitations |
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Authors: | Tanmoy Chanda Rajiv Kumar Verma Dr Maya Shankar Singh |
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Institution: | Department of Chemistry, Faculty of Science, Banaras Hindu University, Varanasi‐221005 (India), Fax: (+91)?542‐2368127 |
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Abstract: | The efficient, regioselective synthesis of functionalized/annulated quinolines was achieved by the coupling of 2‐aminoaryl ketones with alkynes/active methylenes/α‐oxoketene dithioacetals promoted by InCl3 in refluxing acetonitrile as well as under solvent‐free conditions in excellent yields. This transformation presumably proceeded through the hydroamination–hydroarylation of alkynes, and the Friedländer annulation of active methylene compounds and α‐oxoketene dithioacetals with 2‐aminoarylketones. In addition, simple reductive and oxidative cyclization of 2‐nitrobenzaldehyde and 2‐aminobenzylalcohol, respectively, afforded substituted quinolines. Systematic optimization of the reaction parameters allowed us to identify two‐component coupling (2CC) conditions that were tolerant of a wide range of functional groups, thereby providing densely functionalized/annulated quinolines. This approach tolerates the synthesis of various bioactive quinoline frameworks from the same 2‐aminoarylketones under mild conditions, thus making this strategy highly useful in diversity‐oriented synthesis (DOS). The scope and limitations of the alkyne‐, activated methylene‐, and α‐oxoketene dithioacetal components on the reaction were also investigated. |
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Keywords: | annulation cyclization indium quinolines solvent‐free synthesis |
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