Issue 43, 2020

A formal [3 + 2] annulation reaction of propargyl sulfonium compounds and N-ylides: access to pyrrolo[2,1-a]quinolines, pyrrolo[2,1-a]phthalazines and indolizines

Abstract

A sequential [3 + 2] annulation of prop-2-ynylsulfonium salt and N-ylides was developed, leading to the formation of a series of pyrrolo[2,1-a]quinolines, pyrrolo[2,1-a]phthalazines and indolizines. The protocol featured the simultaneous one-pot formation of three new C–C bonds in moderate yields under mild conditions. In this reaction, the prop-2-ynylsulfonium salts acted as the C2 synthons and sulfide served as the leaving group. The resultant products could serve as useful precursors for the synthesis of diverse chemical compounds.

Graphical abstract: A formal [3 + 2] annulation reaction of propargyl sulfonium compounds and N-ylides: access to pyrrolo[2,1-a]quinolines, pyrrolo[2,1-a]phthalazines and indolizines

Supplementary files

Article information

Article type
Paper
Submitted
23 Aug 2020
Accepted
14 Oct 2020
First published
23 Oct 2020

Org. Biomol. Chem., 2020,18, 8867-8875

A formal [3 + 2] annulation reaction of propargyl sulfonium compounds and N-ylides: access to pyrrolo[2,1-a]quinolines, pyrrolo[2,1-a]phthalazines and indolizines

J. Zheng, X. He, H. Xu, H. Liu and W. Yang, Org. Biomol. Chem., 2020, 18, 8867 DOI: 10.1039/D0OB01739F

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