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Paper | Regular issue | Vol 57, No. 12, 2002, pp.2267-2277
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9604
Synthesis of Novel Tetra- and Pentacyclic Fused Benzimidazole Derivatives

Jae Sang Yi and Kyongtae Kim*

*School of Chemistry and Molecular Engineering, Seoul National University, Shillim-Dong, San 56-1, Seoul 151-742 , Korea


Treatment of 7,12-dihydro[5,6][1,3]thiazepino[3,2-a]benzimidazole 6,6-dioxide (1) with NaH (1.2 equiv.) for 30 min in THF at room temperature under nitrogen atmosphere, followed by addition of alkyl propiolate (4 equiv.) gave tetracyclic benzimidazole derivatives (7). Subsequent reactions of 7 with Na in p-xylene at reflux, followed by addition of HOAc at room temperature gave pentacyclic benzimidazole derivative (8) in good to excellent yields.