Premium
Substitution reactions of phenanthro[9,10‐ d ]triazole with benzyl chlorides
Author(s) -
Yasuda Goro,
Kimoto Hiroshi
Publication year - 1998
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.5570350218
Subject(s) - chemistry , yield (engineering) , medicinal chemistry , ring (chemistry) , 1,2,4 triazole , potassium , benzyl chloride , salt (chemistry) , nitro , triazole , chloride , organic chemistry , catalysis , alkyl , materials science , metallurgy
Abstract The reaction of the potassium salt of phenanthro[9,10‐ d ]triazole and benzyl chloride gave 2‐(benzyl)‐2 H ‐phenanthro[9,10‐ d ]triazole ( 2a ) in 15% yield. The other regio‐isomer, 1‐(benzyl)‐1 H ‐phenanthro[9,10‐ d ]‐triazole ( 1a ), was obtained as a by‐product in 3.9% yield. Similar reactions with benzyl chlorides having a methyl, a chloro or a nitro group on the aromatic ring gave the corresponding two products, 1b‐j and 2b‐j . In all cases, 2b‐j were major products in yields of 14–62%, 1b‐j were minor ones in yields of 1.4–7.6%. The structures of the isomers were confirmed by X‐ray crystal analyses.