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Synlett 2021; 32(11): 1117-1122
DOI: 10.1055/a-1479-4420
letter

An Efficient Strategy for the Synthesis of Naphtho[2,3-b][1,6]naphthyridines Promoted by Acetic Acid

Chunmei Li
a   School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province 312000, P. R. of China
b   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032, P. R. of China
,
Furen Zhang∗
a   School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province 312000, P. R. of China
,
Zhenlu Shen  ∗
b   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032, P. R. of China
› Author AffiliationsWe are grateful for financial support from the National Natural Science Foundation of China (21776260) and the Key Research and Development Project of Zhejiang Province (2021C01079) for this research work.
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Abstract

A three-component domino reaction for the synthesis of naphtho[2,3-b][1,6]naphthyridine derivatives has been established. Such strategy exhibited excellent substrate scope including various enaminones and aldehydes that afforded a series of multifunctionalized naphtho[2,3-b][1,6]naphthyridine derivatives with 70–86% yields. The advantages of bond-forming efficiency, accessibility of starting materials, and water as sole byproducts provide invaluable access to biological 1,6-naphthyridines.

Key words

aminopyridinone - 2-hydroxynaphthalene-1,4-dione - naphtho[2,3-b][1,6]naphthyridines - acetic acid - synthesis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1479-4420.
  • Supporting Information


Publication History

Received: 05 March 2021

Accepted after revision: 10 April 2021

Accepted Manuscript online:
10 April 2021

Article published online:
22 April 2021

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