Asian Journal of Organic Chemistry

C‐H Methylthiolation/d3‐ Methylthiolation of Pyrazole Skeleton via Interrupted Pummerer Reaction

Haofeng Shi ^{1, 2}

FENGXIA SUN ^{3, 4}

JIALIANG WU ^{1, 2}

Jiaxin He ^{1, 2}

Yuli Sun ^{1, 2}

Yunfei Du ²

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Tianjin University School of Pharmaceutical Science and Technology CHINA |

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency Faculty of Medicine School of Pharmaceutical Science and Technology Tianjin University Tianjin 300072 China |

Hebei University of Science and Technology Hebei Research Center of Pharmaceutical and Chemical Engineering 050018 Shijiazhuang CHINA |

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Hebei Research Center of Pharmaceutical and Chemical Engineering Hebei University of Science and Technology Shijiazhuang 050018 China |

Publication type: Journal Article

Publication date: 2025-01-08

Wiley

Journal: Asian Journal of Organic Chemistry

scimago Q2

SJR: 0.578

CiteScore: 4.7

Impact factor: 2.8

ISSN: 21935807, 21935815

DOI: 10.1002/ajoc.202400639

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Abstract

The reaction of a series of pyrazole derivatives with DMSO/ ‐DMSO‐d₆ and thionyl chloride conveniently afforded the 4‐thiolated pyrazole products under metal‐free conditions. This C−H functionalization/elelctrophilic thiolation process is postulated to involve the in situ generation of the electrophilic hypochlorothioite via interrupted Pummerer reaction, followed with the electrophilic methylthiolation of pyrazole skeleton.

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Publisher

Wiley

Journal

Asian Journal of Organic Chemistry

scimago Q2

SJR

0.578

CiteScore

4.7

Impact factor

2.8

ISSN

21935807 (Print, Electronic)

21935815 (Electronic)