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

Author:
Gattu, Radhakrishna, Bagdi, Prasanta Ray, Basha, R. Sidick, Khan, Abu T.
Source:
Journal of organic chemistry 2017 v.82 no.23 pp. 12416-12429
ISSN:
1520-6904
Subject:
aldehydes, catalysts, chemical reactions, chemical structure, ketones, organic chemistry, pregnenolone, quinoline
Abstract:
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.
Agid:
5864544