TY - JOUR
T1 - Furopyridines. XXX [1]. Synthesis and reaction of difuro[3,2-c:- 3',2'- e]pyridine, a new tricyclic heterocycle
AU - Shiotani, Shunsaku
AU - Yamaguchi, Seiji
AU - Kurosaki, Masahide
AU - Yokoyama, Hajime
AU - Hirai, Yoshiro
PY - 1999
Y1 - 1999
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0032922208&partnerID=8YFLogxK
U2 - 10.1002/jhet.5570360212
DO - 10.1002/jhet.5570360212
M3 - 学術論文
AN - SCOPUS:0032922208
SN - 0022-152X
VL - 36
SP - 403
EP - 412
JO - Journal of Heterocyclic Chemistry
JF - Journal of Heterocyclic Chemistry
IS - 2
ER -