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Synthesis 2018; 50(11): 2255-2265
DOI: 10.1055/s-0037-1609491
paper
© Georg Thieme Verlag Stuttgart · New York

Catalyst-Free Synthesis of 3-(2-Quinolinemethylene)-Substituted Isoindolinones in Water

Youping Tian
Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, Shaanxi 710062, P. R. of China   Email: fengxu@snnu.edu.cn
,
Jialin Sun
Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, Shaanxi 710062, P. R. of China   Email: fengxu@snnu.edu.cn
,
Kaihua Zhang
Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, Shaanxi 710062, P. R. of China   Email: fengxu@snnu.edu.cn
,
Gaoqiang Li
Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, Shaanxi 710062, P. R. of China   Email: fengxu@snnu.edu.cn
,
Feng Xu*
Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, Shaanxi 710062, P. R. of China   Email: fengxu@snnu.edu.cn
› Author AffiliationsWe are grateful for financial support from the National Natural Science Foundation of China (Nos. 21572123, 21172138 and 21302117), the Fundamental Research Funds for the Central Universities (GK201601003 and GK201603047) and the Distinguished Doctoral Research Funds from Shaanxi Normal University (S2011YB04).
Further Information

Publication History

Received: 05 November 2017

Accepted after revision: 05 March 2018

Publication Date:
28 March 2018 (online)

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Abstract

A facile and environmentally benign approach toward the synthesis of novel 3-alkyl-substituted isoindolinones by three-component reactions of 2-formylbenzoic acids, primary amines and 2-methyl­azaarenes in water under catalyst- and additive-free conditions is described. This protocol features the direct construction of multiple C–N and C–C bonds via a tandem Mannich-type reaction and intramolecular cyclization in a one-pot fashion, affording the desired 3-(2-quinolinemethylene)-substituted isoindolinones in high to excellent yields.

Key words

multicomponent reactions - isoindolines - catalyst-free - Mannich-type reaction - cyclization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609491.
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