A facile one-pot synthesis of 3-amino-[1,2,4]-triazolo[4,3-a]pyridines from thiosemicarbazides through anion mediated synthesis is reported. Thiosemicarbazides derived from 2-hydrazino pyridine, 5-chloro 2-hydrazino pyridine, and 2-hydrazine quinoline were formed in situ as anion receptors in the presence of TBAF. Under microwave heating, thiosemicarbazides furnished the triazolo pyridines in good to moderate yields. The formation of the thiosemicarbazides hydrogen bonding anion receptors was critical in cascading the reaction toward the formation of the triazolo pyridines.
Pandurangan, K., Aletti, A.B., Montroni, D., Kitchen, J.A., MartÃnez-Calvo, M., Blasco, S., et al. (2017). Supramolecular Anion Recognition Mediates One-Pot Synthesis of 3-Amino-[1,2,4]-triazolo Pyridines from Thiosemicarbazides. ORGANIC LETTERS, 19(5), 1068-1071 [10.1021/acs.orglett.6b03645].
Supramolecular Anion Recognition Mediates One-Pot Synthesis of 3-Amino-[1,2,4]-triazolo Pyridines from Thiosemicarbazides
MONTRONI, DEVIS;
2017
Abstract
A facile one-pot synthesis of 3-amino-[1,2,4]-triazolo[4,3-a]pyridines from thiosemicarbazides through anion mediated synthesis is reported. Thiosemicarbazides derived from 2-hydrazino pyridine, 5-chloro 2-hydrazino pyridine, and 2-hydrazine quinoline were formed in situ as anion receptors in the presence of TBAF. Under microwave heating, thiosemicarbazides furnished the triazolo pyridines in good to moderate yields. The formation of the thiosemicarbazides hydrogen bonding anion receptors was critical in cascading the reaction toward the formation of the triazolo pyridines.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
