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Paper | Regular issue | Vol 36, No. 3, 1993, pp.507-518
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6199
Syntheses of 2-Azafluorenones from 3-Substituted 4-Arylpyridines

Min-Jen Shiao,* Kang-Hsiuan Liu, and Pen-Yuan Lin

*Institutue of Chemistry, Academia Sinica, 128, Yan-Chiu-Yuan Road, Sec II, Nankang, Taipei,11529, Taiwan, R.O.C.

Abstract

3-Substituted 4-arylpyridines (5a-i) were synthesized in good yields by reaction of mixed copper, zinc aryl organometallics (2a-e) with 1-ethoxycarbonylpyridinium chlorides (1a-d) followed by o-chloranil oxidation under reflux in toluene. The 4-arylpyridines (5a-i) are obtained predominantly. Having compounds (5a-i) in hand, a convenient method was developed for the synthesis of 2-azafluorenones (7a-f) by using cyclization of 4-arylpyridines (5a-i) with polyphosphoric acid.