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An efficient method for one-pot synthesis of 3-alkoxy-substituted chromeno[4,3-b]pyrrol-4(1H)-one derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

A one-pot two-step reaction of 4-aminocoumarin with arylglyoxal monohydrates and p-toluenesulfonates has been developed, which offers 3-alkoxy-substituted chromeno[4,3-b]pyrrol-4(1H)-ones in moderate to good yields. At first, arylglyoxal monohydrates and 4-aminocoumarin were converted into 3-hydroxychromeno[4,3-b]pyrrol-4(1H)-one intermediates in AcOH under reflux. Then the title compounds in an in situ reaction of the intermediates with p-toluenesulfonates catalyzed by DBU in refluxing toluene were obtained.

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Authors and Affiliations

  1. Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, P. R. China

    Xiaofeng Yang, Lei Jing & Zhiwei Chen

Authors
  1. Xiaofeng Yang
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  2. Lei Jing
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  3. Zhiwei Chen
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Correspondence to Zhiwei Chen.

Additional information

Supplementary information file containing reaction optimization data, as well as 1H and 13C NMR spectra of compounds 3a–o, 4a is available at the journal website at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(11), 1065–1069

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Yang, X., Jing, L. & Chen, Z. An efficient method for one-pot synthesis of 3-alkoxy-substituted chromeno[4,3-b]pyrrol-4(1H)-one derivatives. Chem Heterocycl Comp 54, 1065–1069 (2018). https://doi.org/10.1007/s10593-018-2393-9

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  • DOI: https://doi.org/10.1007/s10593-018-2393-9

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