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Furopyridines. XXX . Synthesis and reaction of difuro[3,2‐ c :‐ 3′,2′‐ e ]pyridine, a new tricyclic heterocycle
Author(s) -
Shiotani Shunsaku,
Yamaguchi Seiji,
Kurosaki Masahide,
Yokoyama Hajime,
Hirai Yoshiro
Publication year - 1999
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.5570360212
Subject(s) - chemistry , nitration , pyridine , formylation , halogenation , acetic anhydride , nitric acid , medicinal chemistry , derivative (finance) , bromine , sulfuric acid , organic chemistry , dimethylformamide , acetic acid , catalysis , solvent , financial economics , economics
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.