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Paper | Special issue | Vol 88, No. 1, 2014, pp.463-474
Published online, 14th August, 2013
DOI: 10.3987/COM-13-S(S)59
Synthesis of Novel Benzofuran Fused 1-Azaazulene Derivative by Tandem Intermolecular Suzuki Coupling/Intramolecular Buchwald-Hartwig Type Coupling

Hiroyuki Fujii,* Kazuya Sanada, Yu Kawai, Reiko Ikeda, Takeo Konakahara, and Noritaka Abe

*Department of Chemistry, Faculty of Science, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan


Synthesis of benzofuran fused 1-azaazulene derivative (cyclohepta[d]benzo[4,5]furano[2,3-b]pyrrole) (4) was achieved successfully by tandem intermolecular Suzuki coupling/intramolecular Buchwald-Hartwig type coupling of 2-chloro-3-iodo-1-azaazulene with 2-hydroxyphenylboronic acid pinacolate in the presence of Pd catalyst. The compound 4 was also obtained by the reaction of 2-chloro-1-azaazulene with 2-iodophenol in the presence of Pd catalyst in one pot. It was considered that the obtained tetra-cyclic heterocycles would consist 18π peripheral conjugated system by the studies of UV/Vis spectra and 1H NMR spectra, together with DFT calculation.