Iodine-Mediated Heterocyclization for the Synthesis of 6-Alkylthio-1,3,5-triazine-2,4-diamines from N-Alkylpyridinium Salts and NH4SCN

Zhiqi Liu; Yinghua Li; Weibin Fan; Deguang Huang

doi:10.1021/acs.joc.3c02517

Iodine-Mediated Heterocyclization for the Synthesis of 6-Alkylthio-1,3,5-triazine-2,4-diamines from N-Alkylpyridinium Salts and NH₄SCN

J Org Chem. 2024 Jan 5;89(1):676-680. doi: 10.1021/acs.joc.3c02517. Epub 2023 Dec 19.

Authors

Zhiqi Liu^{1

2}, Yinghua Li¹, Weibin Fan¹, Deguang Huang^{1

2}

Affiliations

¹ State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China.
² Fujian Normal University, College of Chemistry and Materials Science, Fuzhou 350007, China.

PMID: 38113931
DOI: 10.1021/acs.joc.3c02517

Abstract

An iodine-mediated method for the synthesis of 6-alkylthio-1,3,5-triazine-2,4-diamines by the reaction of N-alkylpyridinium salts and NH₄SCN 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_Bn-S_SCN bond and thereby the construction of the triazine skeleton. A plausible mechanism is proposed based on the experimental results and literature survey.