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Furopyridines. XXII. Elaboration of the C-substituents alpha to the heteronitrogen atom of furo[2,3-b] -, -[3,2-b] -, -[2,3-c]- and -[3,2-c]pyridine

✍ Scribed by Shunsaku Shiotani; Katsunori Tanigochi

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
523 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The Grignard reaction of fused ring cyanopyridine derivatives 1a‐d with methyl‐ and phenylmagnesium bromide yielded the corresponding acylpyridine compounds 2a‐d and 3a‐d. Furopyridine N‐oxides 4a‐d were converted into the compounds having a phenyl group at the α‐position to the ring nitrogen 5a‐d. Reduction of 1a‐d and the carboxylic esters 6a‐d with diisobutylaluminium hydride yielded the corresponding amines 7a‐d and aldehydes 9a‐d. The aldehydes were converted to nitroethanol derivatives 10a‐d by condensation with nitromethane and acrylic ester compounds 11a‐d by the Wittig‐Horner reaction with methyl diethyl phosphonoacetate.

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