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Furopyridines. XXVI. Reactions of cyanopyridine derivatives of furo[2,3-b]-, -[3,2-b]-, -[2,3-c]- and -[3,2-c]pyridine

✍ Scribed by Sciji Yamaguchi; Hideo Saitoh; Masahide Kurosaki; Hajime Yokoyama; Yoshiro Hirai; Shunsaku Shiotani

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

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✦ Synopsis

Abstract

Bromination of α‐cyanopyridine derivatives of furopyridines 1a‐d gave the 2,3‐dibromo‐2,3‐dihydro compounds 2a‐d in excellent yields. Treatment of 2a‐d with sodium hydroxide in methanol yielded compounds formed through the dehydrobromination and solvolysis of the nitrile. N‐Oxidation of 1a and 1b gave N‐oxide in much poor yield, while 1c and 1d gave the N‐oxide 13c and 13d in good yields. The nucleophilic reactions (cyanation, chlorination and acetoxylatoin) of 13c through a Reissert‐Henze type reaction gave poor results, which would be caused by the strong electron withdrawing effect of the cyano group.

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