Iodine-Mediated Heterocyclization for the Synthesis of 6-Alkylthio-1,3,5-triazine-2,4-diamines from N -Alkylpyridinium Salts and NH 4 SCN

An iodine-mediated method for the synthesis of 6-alkylthio-1,3,5-triazine-2,4-diamines by the reaction of -alkylpyridinium salts and NH SCN in air is reported. Twenty-seven compounds were obtained under the standard conditions. Pyridinium salts work as benzyl-group transfer reagents to promote the f...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 89; no. 1; pp. 676 - 680
Main Authors Liu, Zhiqi, Li, Yinghua, Fan, Weibin, Huang, Deguang
Format Journal Article
LanguageEnglish
Published United States 05.01.2024
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Summary:An iodine-mediated method for the synthesis of 6-alkylthio-1,3,5-triazine-2,4-diamines by the reaction of -alkylpyridinium salts and NH SCN in air is reported. Twenty-seven compounds were obtained under the standard conditions. Pyridinium salts work as benzyl-group transfer reagents to promote the formation of the C -S bond and thereby the construction of the triazine skeleton. A plausible mechanism is proposed based on the experimental results and literature survey.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02517