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

Zhiqi Liu,

Yinghua Li, Weibin Fan

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 89(1), С. 676 - 680

Опубликована: Дек. 19, 2023

An iodine-mediated method for the synthesis of 6-alkylthio-1,3,5-triazine-2,4-diamines by reaction N-alkylpyridinium salts and NH4SCN in air is reported. Twenty-seven compounds were obtained under standard conditions. Pyridinium work as benzyl-group transfer reagents to promote formation CBn–SSCN bond thereby construction triazine skeleton. A plausible mechanism proposed based on experimental results literature survey.

Язык: Английский

Iodine(I) and Silver(I) Complexes Incorporating 3-Substituted Pyridines DOI Creative Commons
Kari Rissanen, Jas S. Ward

ACS Omega, Год журнала: 2023, Номер 8(26), С. 24064 - 24071

Опубликована: Июнь 21, 2023

Building upon the first report of a 3-acetaminopyridine-based iodine(I) complex (1b) and its unexpected reactivity toward tBuOMe, several new 3-substituted complexes (2b-5b) have been synthesized. The were synthesized from their analogous silver(I) (2a-5a) via to cation exchange reaction, incorporating functionally related substituents as 3-acetaminopyridine in 1b; 3-acetylpyridine (3-Acpy; 2), 3-aminopyridine (3-NH2py; 3), 3-dimethylaminopyridine (3-NMe2py; 4), well strongly electron-withdrawing 3-cyanopyridine (3-CNpy; 5), probe possible limitations formation. individual properties these rare examples pyridines are also compared each other contrasted 4-substituted counterparts which more prevalent literature. While 1b etheric solvents could not be reproduced any analogues herein, was further expanded second solvent. Reaction bis(3-acetaminopyridine)iodine(I) iPr2O gave [3-acetamido-1-(3-iodo-2-methylpentan-2-yl)pyridin-1-ium]PF6 (1d), demonstrated potentially useful C-C C-I bond formation under ambient conditions.

Язык: Английский

Процитировано

4

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

Zhiqi Liu,

Yinghua Li, Weibin Fan

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 89(1), С. 676 - 680

Опубликована: Дек. 19, 2023

An iodine-mediated method for the synthesis of 6-alkylthio-1,3,5-triazine-2,4-diamines by reaction N-alkylpyridinium salts and NH4SCN in air is reported. Twenty-seven compounds were obtained under standard conditions. Pyridinium work as benzyl-group transfer reagents to promote formation CBn–SSCN bond thereby construction triazine skeleton. A plausible mechanism proposed based on experimental results literature survey.

Язык: Английский

Процитировано

1