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Dipyrido[1,2‐b:3′,4′‐e][1,2,4]triazine Scaffolds from Pentafluoropyridine
Author(s) -
RanjbarKarimi Reza,
Darehkordi Ali,
Bahadornia Fahimeh,
Poorfreidoni Alireza
Publication year - 2018
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3283
Subject(s) - chemistry , pyridine , ring (chemistry) , nucleophilic substitution , intramolecular force , triazine , annulation , stereochemistry , nucleophile , aryl , proton nmr , medicinal chemistry , organic chemistry , alkyl , catalysis
Annelation reaction between pentafluoropyridine and diaminodihydro substituted pyridine derivatives gave dipyrido[1,2‐b:3′,4′‐e][1,2,4]triazine systems as major products arising from the initial nucleophilic substitution of more nucleophilic N ‐amino group of pyridone ring at 4‐position of the pyridine ring followed by intramolecular cyclization at 3‐position of pyridine ring. Also, 6‐amino‐2‐oxo‐1‐((perfluoropyridin‐4‐yl)amino)‐4‐aryl‐1,2‐dihydropyridine‐3,5‐dicarbonitrile derivatives were obtained as side products. The structures of all the compounds were confirmed by IR, 1 H NMR, 13 C NMR, and 19 F NMR spectroscopy as well as elemental analysis.