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

✍ Scribed by Goro Yasuda; Hiroshi Kimoto

Publisher: Journal of Heterocyclic Chemistry
Year: 1998
Tongue: English
Weight: 390 KB
Volume: 35
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570350218

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✦ Synopsis

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.

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