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Paper | Regular issue | Vol 55, No. 4, 2001, pp.741-752
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9168
Polycyclic N-Heterocyclic Compounds. 57 Syntheses of Fused Furo(or Thieno)[2,3-b]pyridine Derivatives via Smiles Rearrangement and Cyclization

Takashi Hirota,* Kei-ichiroh Tomita, Kenji Sasaki, Kensuke Okuda, Masahiko Yoshida, and Setsuo Kashino

*Faculty of Pharmaceutical Science, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan


An efficient methodology for the synthesis of thieno[2,3-c][2,7]naphthyridine (6), thieno[2,3-c]isoquinoline (11), furo[2,3-c]isoquinoline (14), [1]benzothieno[3,2-d]thieno[2,3-b]pyridine (21), and [1]benzothieno[3,2-d]furo[2,3-b]pyridine (26) skeletons from 4-[o-cyanoarylthio(or oxy)]butyronitriles with base via Smiles type rearrangement reaction followed by the cyclization is described.