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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
Author(s) -
Shiotani Shunsaku,
Tanigochi Katsunori
Publication year - 1997
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.5570340329
Subject(s) - chemistry , phenylmagnesium bromide , ring (chemistry) , nitrogen atom , grignard reaction , medicinal chemistry , nitromethane , magnesium bromide , hydride , bromide , stereochemistry , organic chemistry , hydrogen , magnesium , reagent
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.