An Yb(OTf)3‐catalyzed, convergent synthesis of new pyranyl‐ and chromenyl‐substituted quinolines through an eco‐friendly approach

A one‐pot, multicomponent, convergent microwave synthesis of some new pyranyl‐ and chromenyl‐substituted quinolines has been reported. Twenty compounds were prepared by the reaction of 2‐methoxy‐3‐formyl quinoline (1a‐d), malononitrile (2), and kojic acid (4a‐d)/1,3‐cyclohexadione or dimedone (6a‐h)...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2019-11, Vol.56 (11), p.2986-2992
Main Authors: Kumarasamy, Chandraprakash, Sundarasamy, Amsaveni, Mathan, Sankaran, Chokkalingam, Uvarani, Athar, Ata, Subramaniam, Mohan Palathurai, Thangaraj, Suresh
Format: Article
Language:English
Subjects:
Catalysts
Chemical synthesis
Convergence
Lewis acid
Malononitrile
Naphthol
NMR
Nuclear magnetic resonance
Organic compounds
Quinoline
Substitutes
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Summary:A one‐pot, multicomponent, convergent microwave synthesis of some new pyranyl‐ and chromenyl‐substituted quinolines has been reported. Twenty compounds were prepared by the reaction of 2‐methoxy‐3‐formyl quinoline (1a‐d), malononitrile (2), and kojic acid (4a‐d)/1,3‐cyclohexadione or dimedone (6a‐h)/α‐ or β‐naphthol (8a‐d, 8e‐h). The structures were confirmed by infrared (IR), 1H nuclear magnetic resonance (NMR), 13C NMR, mass, and single‐crystal X‐ray analyses. On comparison with the use of conventional Lewis acid catalysts and various metal triflates under microwave conditions, the latter contributed to good yields, in specific use of the recyclable Yb(OTf)3 catalyst attributed to high yields of the desired product. The protocol reported herein is solvent free, cost effective, and eco‐friendly.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.3692