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Furopyridines. XXV. Synthesis of 5-substituted furo [2,3-b]pyridines

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

Publisher
Journal of Heterocyclic Chemistry
Year
1998
Tongue
English
Weight
246 KB
Volume
35
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Derivatives (2–8) of furo[2,3‐b]pyridine having a substituent at the β‐position to the ring nitrogen were prepared from the 5‐nitro compound 1 via the Sandmeyer reaction.

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In a three-step sequence starting from readily available starting materials, 2,3-carbon disubstituted furo[2,3-b]pyridines can be accessed in good yields and purity. Furo[2,3-b]pyridines bearing ester, amide and ketone groups at the 2-position can be prepared with a variety of aryl and alkyl groups

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## Abstract Chlorination of the __N__‐oxides of furo[2,3‐__b__]‐ 1a, ‐[2,3‐__c__]‐ 1b and ‐[3,2‐c]pyridine 1c with phosphorus oxychloride afforded compounds substituted normally at the α‐ or λ‐position to the ring nitrogen, 2a, 2β€²a, 2b, 2c, 2β€²c and 2β€²c, and in addition, in the case of 1b, compounds

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## 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__‐Oxidatio