Base-controlled annulation of tryptamine-derived isocyanides with nitrile imines for access to polycyclic spiroindoline derivatives

Xiaofeng Wang; Luorong Yuan; Xiaoping Xu; Shunjun Ji

Green Synthesis and Catalysis (May 2023)

Base-controlled annulation of tryptamine-derived isocyanides with nitrile imines for access to polycyclic spiroindoline derivatives

Xiaofeng Wang,
Luorong Yuan,
Xiaoping Xu,
Shunjun Ji

Affiliations

Xiaofeng Wang: Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China
Luorong Yuan: Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China
Xiaoping Xu: Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China; Innovation Center for Chemical Science, Soochow University, Suzhou 215144, China; Corresponding authors. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China.
Shunjun Ji: Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China; Suzhou Baolidi Functional Materials Research Institute, Suzhou 215144, China; Corresponding authors. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China.

Journal volume & issue: Vol. 4, no. 2
pp. 181 – 185

Abstract

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An annulation reaction of tryptamine-derived isocyanides with hydrazonyl chlorides in the presence of bases was developed. Controlled by different bases, [1+ 2+3] annulation and [1+ 2+3]/[2 + 3] annulation cascade were realized. In the latter reaction, five new chemical bonds as well as three new heterocycles were formed in one step. It showed extremely high efficiency, relatively broad substrate scope, milder reaction conditions, good tolerance of functional groups and good chemoselectivity.

Published in Green Synthesis and Catalysis

ISSN: 2666-5549 (Online)
Publisher: KeAi Communications Co. Ltd.
Country of publisher: China
LCC subjects: Technology: Chemical technology; Science: Chemistry: Organic chemistry: Biochemistry
Website: https://www.keaipublishing.com/en/journals/green-synthesis-and-catalysis/

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