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Short Paper | Regular issue | Vol 98, No. 7, 2019, pp.966-976
Published online, 12th July, 2019
DOI: 10.3987/COM-19-14093
A Convenient Approach to the Synthesis of Novel Tricyclic Fused Furo[2,3-b]pyridine Derivatives

Fumi Okabe-Nakahara,* Kazuhiro Tomoike, Hayate Nagabuchi, Eiichi Masumoto, Hiroshi Maruoka, and Kenji Yamagata

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

The synthesis of novel tricyclic fused furo[2,3-b]pyridine derivatives is described. 3-Cyano-4,5-dihydro-2-furan(and 2-thiophene)acetonitriles 1,2 were reacted with phenacyl bromides to give 5'-arylfuran-2'-amines 3,4. Compounds 3,4 were intramolecularly cyclized in the presence of sodium ethoxide to yield tricyclic fused furo[2,3-b]pyridine derivatives 5,6. Furthermore, one-pot synthesis of compounds 5,6 from starting materials 1,2 is also developed.