NIS-promoted carbochalcogenation of styrenes: regioselective C-3 alkylation of pyrazolo[1,5-a]pyrimidines

Abhinay S. Chillal; Varsha Kumari; Umesh A. Kshirsagar

doi:10.1039/d5ob00303b

NIS-promoted carbochalcogenation of styrenes: regioselective C-3 alkylation of pyrazolo[1,5-a]pyrimidines

Abhinay S. Chillal, Varsha Kumari, Umesh A. Kshirsagar

Research output: Contribution to journal › Article › peer-review

Abstract

An N-iodosuccinimide (NIS) mediated transition metal and solvent-free, regioselective multicomponent cascade reaction is developed for the C-3 alkylation of pyrazolo[1,5-a]pyrimidines via a three-component reaction of styrenes, diaryl dichalcogenides and pyrazolo[1,5-a]pyrimidines. This operationally simple, cost-effective and rapid reaction furnishes C-3 functionalized pyrazolo[1,5-a]pyrimidines in good to excellent yields. The reaction is scalable and operates via an electrophilic substitution mechanism.

Original language	English
Pages (from-to)	4365-4370
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	23
Issue number	18
DOIs	https://doi.org/10.1039/d5ob00303b
State	Published - 7 Apr 2025
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "An N-iodosuccinimide (NIS) mediated transition metal and solvent-free, regioselective multicomponent cascade reaction is developed for the C-3 alkylation of pyrazolo[1,5-a]pyrimidines via a three-component reaction of styrenes, diaryl dichalcogenides and pyrazolo[1,5-a]pyrimidines. This operationally simple, cost-effective and rapid reaction furnishes C-3 functionalized pyrazolo[1,5-a]pyrimidines in good to excellent yields. The reaction is scalable and operates via an electrophilic substitution mechanism.",

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AU - Kumari, Varsha

AU - Kshirsagar, Umesh A.

PY - 2025/4/7

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AB - An N-iodosuccinimide (NIS) mediated transition metal and solvent-free, regioselective multicomponent cascade reaction is developed for the C-3 alkylation of pyrazolo[1,5-a]pyrimidines via a three-component reaction of styrenes, diaryl dichalcogenides and pyrazolo[1,5-a]pyrimidines. This operationally simple, cost-effective and rapid reaction furnishes C-3 functionalized pyrazolo[1,5-a]pyrimidines in good to excellent yields. The reaction is scalable and operates via an electrophilic substitution mechanism.

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NIS-promoted carbochalcogenation of styrenes: regioselective C-3 alkylation of pyrazolo[1,5-a]pyrimidines

Abstract

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