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Synthesis and crystal structure of piperidinium 2‐aryl[1,2,4]triazolo[1,5‐ a ]pyridinides and their neutralization to 2‐aryl[1,2,4]triazolo[1,5‐ a ]pyridines
Author(s) -
Hadi Alí,
Martín Nazario,
Seoane Carlos,
Soto José L.,
Albert Armando,
Cano Félix
Publication year - 1992
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.5570290531
Subject(s) - chemistry , aryl , stacking , hydrochloric acid , hydrogen bond , crystal structure , medicinal chemistry , ion , solvent , crystallography , stereochemistry , molecule , organic chemistry , alkyl
A one step synthesis of novel piperidinium 2‐aryl[1,2,4]triazolo[1,5‐ a ]pyridinides 6 from 2′‐benzoyl‐2‐cyanoacetohydrazide (2) and α‐substituted cinnamonitriles 3 is described. The reaction takes place by 6‐exodig cyclization followed by an 5‐exo‐trig process to afford salts 6 . The X‐ray diffraction of compound 6a reveal that the cation is strongly linked to the anion by hydrogen bonds and a characteristic partial stacking motive. 2‐Aryl[1,2,4]triazolo[1,5‐ a ]pyridines were obtained from salts 6 by treatment with hydrochloric acid.