Issue 5, 2016
From the journal:

Chemical Communications

Unexpected isocyanide-based three-component bicyclization for the stereoselective synthesis of densely functionalized pyrano[3,4-c]pyrroles†

Qian Gao,a   Wen-Juan Hao,a   Feng Liu,a   Shu-Jiang Tu,*a   Shu-Liang Wang,a   Guigen Li*bc  and  Bo Jiang*a  

* Corresponding authors

a School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China
E-mail: laotu@jsnu.edu.cn, jiangchem@jsnu.edu.cn
Fax: +86 51683500065
Tel: +86 51683500065

b Institute of Chemistry & BioMedical Sciences, Collaborative Innovation Center of Chemistry for Life Sciences, Nanjing University, Nanjing 210093, P. R. China

c Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA
E-mail: guigen.li@ttu.edu.cn

Abstract

A novel three-component bicyclization strategy for the efficient synthesis of densely functionalized pyrano[3,4-c]pyrroles has been established from readily accessible 3-aroylacrylic acids, dialkyl acetylenedicarboxylates and isocyanides. The reaction pathway involves Huisgen 1,3-dipole formation, Passerini-type reaction, Mumm rearrangement and an oxo-Diels–Alder reaction sequence, resulting in continuous multiple bond-forming events including C–N, C–O and C–H bonds to rapidly build up molecular complexity.

Graphical abstract: Unexpected isocyanide-based three-component bicyclization for the stereoselective synthesis of densely functionalized pyrano[3,4-c]pyrroles

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Article information

DOI
https://doi.org/10.1039/C5CC08071A
Article type
Communication
Submitted
26 Sep 2015
Accepted
06 Nov 2015
First published
06 Nov 2015

Chem. Commun., 2016,52, 900-903

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Unexpected isocyanide-based three-component bicyclization for the stereoselective synthesis of densely functionalized pyrano[3,4-c]pyrroles

Q. Gao, W. Hao, F. Liu, S. Tu, S. Wang, G. Li and B. Jiang, Chem. Commun., 2016, 52, 900 DOI: 10.1039/C5CC08071A

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