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Issue 9, 2018
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Solid acid-catalyzed domino cyclization reaction: regio- and diastereoselective synthesis of pyrido[2,3-d]pyrimidine derivatives bearing three contiguous stereocenters

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Abstract

An efficient and green domino approach for the synthesis of 5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-4(3H)-one derivatives using a recoverable carbonaceous material as a catalyst has been established. The new domino reaction was conducted by reacting the readily available and inexpensive starting materials 2,6-diaminopyrimidin-4(3H)-one, nitroolefin and aldehyde in water. A total of 24 examples were examined, and showed a broad substrate scope and high yields. The carbonaceous material catalyst can be reused at least 5 times without obvious deactivation. The proposed mechanism has explained the reaction process and the resulting high regio- and diastereoselectivities. The present green strategy shows attractive characteristics such as using water as a green medium, using an inexpensive and recoverable solid acid catalyst, and having a simple work-up/purification, without generating any waste products or using any metal promoters.

Graphical abstract: Solid acid-catalyzed domino cyclization reaction: regio- and diastereoselective synthesis of pyrido[2,3-d]pyrimidine derivatives bearing three contiguous stereocenters

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Publication details

The article was received on 21 Dec 2017, accepted on 20 Mar 2018 and first published on 23 Mar 2018


Article type: Paper
DOI: 10.1039/C7GC03812G
Citation: Green Chem., 2018,20, 2057-2063
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    Solid acid-catalyzed domino cyclization reaction: regio- and diastereoselective synthesis of pyrido[2,3-d]pyrimidine derivatives bearing three contiguous stereocenters

    F. Zhang, C. Li and X. Liang, Green Chem., 2018, 20, 2057
    DOI: 10.1039/C7GC03812G

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