Synthesis of N-Trifluoromethyl Thiocarbamates and Ureas from 3-Aminopyridine-Derived Carbamates

Xingjin He; Linbei Deng; Ying You; Yongxing Lai; Jianbo Liu

doi:10.1055/a-2290-6614

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(13): 2118-2126
DOI: 10.1055/a-2290-6614

paper

Synthesis of N-Trifluoromethyl Thiocarbamates and Ureas from 3-Aminopyridine-Derived Carbamates

Xingjin He

^aDepartment of Nuclear Medicine, The First Affiliated Hospital of Sun Yat-sen University, 58 Zhongshan Road 2, Guangzhou 510080, P. R. of China

,

Linbei Deng

^bFetal Medicine Center, Department of Obstetrics, The First Affiliated Hospital of Sun Yat-sen University, 58 Zhongshan Road 2, Guangzhou 510080, P. R. of China

,

Ying You

^aDepartment of Nuclear Medicine, The First Affiliated Hospital of Sun Yat-sen University, 58 Zhongshan Road 2, Guangzhou 510080, P. R. of China

,

Yongxing Lai

^aDepartment of Nuclear Medicine, The First Affiliated Hospital of Sun Yat-sen University, 58 Zhongshan Road 2, Guangzhou 510080, P. R. of China

,

Jianbo Liu∗

^aDepartment of Nuclear Medicine, The First Affiliated Hospital of Sun Yat-sen University, 58 Zhongshan Road 2, Guangzhou 510080, P. R. of China

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Abstract

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Abstract

The synthesis of N-trifluoromethyl thiocarbamates and ureas from 3-pyridyl isothiocyanates via the nucleophilic substitution reaction of perfluorophenyl pyridin-3-yl(trifluoromethyl)carbamate is described. Recently, Schoenebeck’s group reported a straightforward method to access N-trifluoromethyl analogues of amides and related carbonyl compounds. However, N-trifluoromethyl thiocarbamates and ureas derived from pyridine-containing amines remain a synthetic challenge. In this paper, the strategy relies on the operationally simple preparation of perfluorophenyl pyridin-3-yl(trifluoromethyl)carbamates, which can smoothly undergo nucleophilic substitution reactions with thiophenol, sodium mercaptide, and amine. Various functional groups such as amide, halogen, ether, and ester were tolerated under these reaction conditions. Notably, alkylamine structures containing pyridine heterocyclic rings are also compatible to access N-trifluoromethyl thiocarbamates.

Key words

N-trifluoromethyl thiocarbamate - N-trifluoromethyl urea - pyridine-containing amine - alkylamine - nucleophilic substitution

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Referenzen

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