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Paper | Regular issue | Vol 53, No. 1, 2000, pp.15-26
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8703
Cathylation of 4,6-Dimethyl-2-oxopyridine-3-carbonitrile Derivatives Leading to the Synthesis of Furo[2,3-b;4,5-b’]dipyridines and Novel Tricyclic Furo[2,3,4-ij][2,7]naphthyridine

Chyun-Feng Lin, Yi-Feng Lin, Yan-Chung Lo, Kuo-Tung Chen, and Tsann-Long Su*

*Institute of Biomedical Sciences, Academia Sinica, Nankang, Taipei 11529, Taiwan, R.O.C.

Abstract

Cathylation of ethyl 2-(3-cyano-4,6-dimethylpyridine-2-yloxy)acetate afforded a trace amount of new tricyclic furo[2,3,4-ij][2,7]naphthyridine derivative. An attempt was made for an alternate method for the synthesis this new tricyclic ring system. Treatment of 4,6-dimethyl-2-oxopyridine-3-carbonitrile (1) with various α-halocarbonyl compounds (such as chloropropanone or substituted 2-bromoacetophenones) gave a mixture of N- and O-alkylated compounds, which were readily converted into indolizines and 2-acetyl-3-amino- or 3-amino-2-benzoylfuro[2,3-b]pyridines. The 3-aminofuro[2,3-b]pyridine derivatives were further converted into furo[2,3-b;4,5-b’]dipyridines, but not the expected tricyclic furonaphthyridines, via N,O-acetylation and cyclization.