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Synthesis of novel and diverse naphtho[1,2-b]furans by phosphine-catalyzed [3+2] annulation of activated 1,4-naphthoquinones and acetylenecarboxylates

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Abstract

A new phosphine-catalyzed [3+2] annulation reaction between activated 1,4-naphthoquinones and acetylenecarboxylates is described. This reaction provides a facile and efficient route to a variety of biologically promising and novel naphtho[1,2-\(b\)]furans. This devised method provides a first example for the synthesis of diverse naphtho[1,2-\(b\)]furan derivatives from 1,4-naphthoquinones via phosphine-catalyzed [3+2] annulation.

Graphical Abstract

A variety of novel naphtho[1,2-\(b\)]furans were synthesized via the phosphine-catalyzed [3+2] annulation of activated 1,4-naphthoquinones and electron-deficient acetylenecarboxylates. In some reactions, both furannulation adducts and reductive/nucleophilic conjugate addition products were produced.

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Acknowledgments

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2012R1A1A4A01009620).

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Authors and Affiliations

  1. School of Chemical Engineering, Yeungnam University, Gyeongsan, 712-749, Republic of Korea

    Likai Xia, Krishna Bahadur Somai Magar & Yong Rok Lee

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  1. Likai Xia
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  2. Krishna Bahadur Somai Magar
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Correspondence to Yong Rok Lee.

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Xia, L., Somai Magar, K.B. & Lee, Y.R. Synthesis of novel and diverse naphtho[1,2-b]furans by phosphine-catalyzed [3+2] annulation of activated 1,4-naphthoquinones and acetylenecarboxylates. Mol Divers 19, 55–66 (2015). https://doi.org/10.1007/s11030-014-9555-1

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