Synthesis of novel imidazole-based triheterocycles via a domino Ugi/Michael reaction and silver-catalyzed heteroannulation

Zhenghua Li; Yaping Zhao; Guilong Tian; Yi He; Gonghua Song; Luc Van Meervelt; Erik V. Van der Eycken

doi:10.1039/C6RA23180B

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Synthesis of novel imidazole-based triheterocycles via a domino Ugi/Michael reaction and silver-catalyzed heteroannulation†

Zhenghua Li,‡^a Yaping Zhao,‡^ab Guilong Tian,^a Yi He,^a Gonghua Song,^ab Luc Van Meervelt

^c and Erik V. Van der Eycken*^a

Author affiliations

* Corresponding authors

^a Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), University of Leuven (KU Leuven), Celestijnenlaan 200F, B-3001 Leuven, Belgium
E-mail: erik.vandereycken@chem.kuleuven.be

^b Shanghai Key Laboratory of Chemical Biology, East China University of Science and Technology, Shanghai 200237, People's Republic of China

^c Biomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, Belgium

Abstract

An efficient and diversity-oriented synthetic strategy for novel triheterocyclic imidazo-pyrrolo-pyrazine/diazepine/diazocine derivatives is elaborated. The process utilizes a domino four-component Ugi reaction/Michael reaction of imidazole-2-carbaldehyde, propargyl amines, 2-alkynoic acids and isonitriles to deliver functionalized imidazole-pyrrolones, which upon a silver-catalyzed heteroannulation in aqueous medium under microwave irradiation furnishes the desired triheterocycles in good to excellent yields.

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Article information

DOI: https://doi.org/10.1039/C6RA23180B
Article type: Communication
Submitted: 17 Sep 2016
Accepted: 24 Oct 2016
First published: 26 Oct 2016

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RSC Adv., 2016,6, 103601-103605

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Synthesis of novel imidazole-based triheterocycles via a domino Ugi/Michael reaction and silver-catalyzed heteroannulation

Z. Li, Y. Zhao, G. Tian, Y. He, G. Song, L. Van Meervelt and E. V. Van der Eycken, RSC Adv., 2016, 6, 103601 DOI: 10.1039/C6RA23180B

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