Cyclization reactions of homopropargyl azide derivatives catalyzed by PtCl4 in ethanol solution: synthesis of functionalized pyrrole derivatives

Kou Hiroya; Shigemitsu Matsumoto; Masayasu Ashikawa; Kentaro Ogiwara; Takao Sakamoto

doi:10.1021/ol062249c

Cyclization reactions of homopropargyl azide derivatives catalyzed by PtCl4 in ethanol solution: synthesis of functionalized pyrrole derivatives

Org Lett. 2006 Nov 9;8(23):5349-52. doi: 10.1021/ol062249c.

Authors

Kou Hiroya¹, Shigemitsu Matsumoto, Masayasu Ashikawa, Kentaro Ogiwara, Takao Sakamoto

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba-ku, Sendai 980-8578, Japan. hiroya@mail.tains.tohoku.ac.jp

PMID: 17078715
DOI: 10.1021/ol062249c

Abstract

[Structure: see text] PtCl4-catalyzed cyclization reactions of homopropargyl azide derivatives to pyrrole rings were investigated. Using ethanol as solvent with 2,6-di-tert-butyl-4-methylpyridine as the base was found to be the best set of conditions for effecting this ring-closing reaction. These reaction conditions can be applied to the preparation of functionalized pyrrole derivatives, with no effect on the functional groups.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Azides / chemistry*
Catalysis
Cyclization
Ethanol / chemistry*
Molecular Structure
Platinum Compounds / chemistry*
Pyrroles / chemistry*

Substances

Azides
Platinum Compounds
Pyrroles
Ethanol
platinum tetrachloride