50871-90-4Relevant academic research and scientific papers
An expedient route to the azoles through oxidative desulfurization using iodine reagent
Jadhav, Nikhil C.,Jagadhane, Prashant B.,Patel, Kavitkumar N.,Telvekar, Vikas N.
, p. 101 - 105 (2013)
A novel and expedient regioselective method for the synthesis of 5-aminotetrazoles and 3-amino-1,2,4-triazoles through oxidative desulfurization of corresponding 1,3-disubstituted thioureas has been discovered and optimized for the process conditions. The process is broadly applicable to structurally diverse 1,3-disubstituted thioureas.
Tandem synthesis of [1,2,4]-triazoles mediated by iodine - A regioselective approach
Guin, Srimanta,Rout, Saroj Kumar,Khatun, Nilufa,Ghosh, Tuhin,Patel, Bhisma K.
experimental part, p. 5066 - 5074 (2012/07/28)
A tandem regioselective one-pot synthesis of 3-amino-[1,2,4]-triazoles has been achieved from 1,3-disubstituted thioureas using molecular iodine. In this one-pot strategy, the intermediate carbodiimide generated in situ from thiourea upon reaction with HCONHNH2 gives diaryl/ alkylhydrazinecarboximidamide or acylureidrazone, which then undergoes an intramolecular cyclodehydration to afford the corresponding 3-amino-[1,2,4]- triazole. The product regioselectivity for unsymmetrical 1,3-disubstituted thioureas correlate well with the pKas of the parent amines attached, in which the amine having higher pKa goes to the ring nitrogen while the other nitrogen remains flanked as an exocyclic nitrogen of the triazole core. This method is milder and environmentally sustainable giving good to excellent yields of the desired products.
