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Furopyridines. XXX. Synthesis and reaction of difuro[3,2-c:- 3′,2′-e]pyridine, a new tricyclic heterocycle

✍ Scribed by Shunsaku Shiotani; Seiji Yamaguchi; Masahide Kurosaki; Hajime Yokoyama; Yoshiro Hirai

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
645 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Difuro[3,2‐c:3′,2′‐e]pyridine 1, a new tricyclic heteroaromatic, has been prepared for the first time. Bromination of 1 with molecular bromine gave 3‐bromo 7, 8‐bromo 7′ and 3,8‐dibromo derivative 8; nitration with fuming nitric acid yielded 2‐nitro compound 9, while nitration with a mixture of fuming nitric acid and sulfuric acid gave 2,7‐dinitro derivative 10; formylation with n‐butyllithium and dimethylformamide gave 2‐formyl 11, 7‐formyl 11′, and 2,7‐diformyl compound 12. The N‐oxide 14 of 1 afforded 4‐cyano compound 15 by cyanation with trimethylsilyl cyanide, 4‐chloro compound 16 by chlorination with phosphorus oxychloride, and 4‐acetoxyl compound 17 by acetoxylation with acetic anhydride.

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