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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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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cited_by cdi_FETCH-LOGICAL-c2122-8bb869bca1ecda8257515edd1761404334de487e5ccd09636a11293ef104bb233
cites cdi_FETCH-LOGICAL-c2122-8bb869bca1ecda8257515edd1761404334de487e5ccd09636a11293ef104bb233
container_end_page 2992
container_issue 11
container_start_page 2986
container_title Journal of heterocyclic chemistry
container_volume 56
creator Kumarasamy, Chandraprakash
Sundarasamy, Amsaveni
Mathan, Sankaran
Chokkalingam, Uvarani
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Subramaniam, Mohan Palathurai
Thangaraj, Suresh
description 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.
doi_str_mv 10.1002/jhet.3692
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subjects Catalysts
Chemical synthesis
Convergence
Lewis acid
Malononitrile
Naphthol
NMR
Nuclear magnetic resonance
Organic compounds
Quinoline
Substitutes
title An Yb(OTf)3‐catalyzed, convergent synthesis of new pyranyl‐ and chromenyl‐substituted quinolines through an eco‐friendly approach
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