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Updated: Sep 15, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Sulfoxide-Controlled Chlorination of Pyrrolo[2,1-a]isoquinoline with Acetyl Chloride
Man Jiang1, Jing Zhou1, Hai-Lei Cui1
1Laboratory of Asymmetric Synthesis, College of Chemistry and Environmental Engineering, Chongqing University of Arts and Sciences, 319 Honghe Ave., Yongchuan, Chongqing 402160, P. R. China.
Abstract:
A sulfoxide-controlled modification of pyrrolo[2,1-a]isoquinoline derivatives has been explored using acetyl chloride. In the presence of AcCl and PhSOPh, the dichlorination of methoxy-bearing pyrrolo[2,1-a]isoquinolines could be achieved at both the pyrrolic moiety and the phenolic ether moiety. Monochlorination of pyrrolo[2,1-a]isoquinoline derivatives occurred solely by the replacement of diphenyl sulfoxide with tetramethylene sulfoxide or dimethyl sulfoxide (3 equiv). In addition, methylenation was realized selectively by treating pyrrolo[2,1-a]isoquinolines with AcCl and an excess amount of dimethyl sulfoxide.
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