Substitution reactions of phenanthro[9,10-d]triazole with benzyl chlorides

The reaction of the potassium salt of phenanthro[9,10-d]triazole and benzyl chloride gave 2-(benzyl)-2H-phenanthro[9,10-d]triazole (2a) in 15% yield. The other regio-isomer, 1-(benzyl)-1H-phenanthro[9,10-d]-triazole (la), was obtained as a by-product in 3.9% yield. Similar reactions with benzyl chlo...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 35; no. 2; pp. 365 - 369
Main Authors Yasuda, G, Kimoto, H
Format Journal Article
LanguageEnglish
Published ODESSA HETERO CORPORATION 01.03.1998
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
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Summary:The reaction of the potassium salt of phenanthro[9,10-d]triazole and benzyl chloride gave 2-(benzyl)-2H-phenanthro[9,10-d]triazole (2a) in 15% yield. The other regio-isomer, 1-(benzyl)-1H-phenanthro[9,10-d]-triazole (la), 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%, 1-bj were minor ones in yields of 1.4-7.6%. The structures of the isomers were confirmed by X-ray crystal analyses.
ISSN:0022-152X
DOI:10.1002/jhet.5570350218