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On triazoles XXIV . Synthesis of cycloalka[1,2,4]triazolo[1,5‐ a ]pyrimidinones
Author(s) -
Reiter József,
Berecz Gábor,
Pallagi István
Publication year - 1991
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.5570280329
Subject(s) - chemistry , pyrimidinones , yield (engineering) , ring (chemistry) , d 1 , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , materials science , receptor , metallurgy
The uv and nmr spectral data of some 6,7,8,9,10,11‐hexahydrocyclohepta[ d ][1,2,4]triazolo[1,5‐ a ]pyrimidin‐5‐one, 5,6,7,8,9,11‐hexahydrocyclohepta[ e ][1,2,4]triazolo[1,5‐ a ]pyrimidin‐10‐one, 6,7,8,9,10,11‐hexahydrocycloocta[ d ][1,2,4]triazolo[1,5‐ a ]pyrimidin‐5(12 H )‐one, 5,6,7,8,9,10‐hexahydrocycloocta[ e ][1,2,4]triazolo[1,5‐ a ]‐pyrimidin‐11(12 H )‐one, 6,7,8,9,10,11,12,13,14,15‐decahydrocyclododeca[ d ][1,2,4]triazolo[1,5‐ a ]pyrimidin‐5(16 H )‐one and 5,6,7,8,9,10,11,12,13,14‐decahydrocyclododeca[ e ][1,2,4]triazolo[1,5‐ a ]pyrimidin‐15(16 H )‐one as well as their N ‐benzylated derivatives representing six novel ring systems were compared to prove their structure. The N ‐benzylation of the highly insoluble cyclic amides to yield the isomeric N ‐benzyl derivatives 3/1, 3/2 and 3/3 distinguished by INAPT was performed through their readily soluble tetrabutylammonium salts.