Camphorsulfonic Acid Catalyzed One-Pot Three-Component Reaction for the Synthesis of Fused Quinoline and Benzoquinoline Derivatives

A simple and an efficient one-pot three-component reaction of arylamines, aromatic aldehydes, and cyclic ketones was described for the synthesis of various fused quinoline, benzoquinoline, and naphthoquinoline derivatives by using camphorsulfonic acid as a catalyst. The exploitation of pregnenolone...

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Veröffentlicht in:Journal of organic chemistry 2017-12, Vol.82 (23), p.12416-12429
Hauptverfasser: Gattu, Radhakrishna, Bagdi, Prasanta Ray, Basha, R. Sidick, Khan, Abu T
Format: Artikel
Sprache:eng
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Zusammenfassung:A simple and an efficient one-pot three-component reaction of arylamines, aromatic aldehydes, and cyclic ketones was described for the synthesis of various fused quinoline, benzoquinoline, and naphthoquinoline derivatives by using camphorsulfonic acid as a catalyst. The exploitation of pregnenolone steroid for benzoquinolines and terephthalaldehyde for bis-benzoquinolines synthesis was achieved with 68–75% yields. The reactivity of arylamines and the mechanistic study for the formation of benzoquinoline was described precisely. The present protocol offers a great potential for atom-economy under mild conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02159