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Communication | Regular issue | Vol 14, No. 1, 1980, pp.39-41
Published online, 1st January, 1970
DOI: 10.3987/R-1980-01-0039
The Reaction of Heteroaromatic Amine Oxides with TiCl4/NaBH4

Shinzo Kano,* Yasuyuki Tanaka, and Satoshi Hibino

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

Treatment of 2-, 3-, 4-picoline N-oxides and 2,6-dimethylpyridine N-oxide with TiCl4 /NaBH4 in dimethoxyethane afforded the corresponding picolines and 2,6-dimethylpyridine in acceptable yields. The same reaction of quinaldine N-oxide and benzo[h]quinoline N-oxide successfully gave quinaldine and benzo[h]quinoline, respectively. In the case of quinoline N-oxide, 1,2,3,4-tetrahydroquinoline and quinoline were obtained. On the other hand, lepidine N-oxide and isoquinoline N-oxide afforded the corresponding 1,2-dihydro derivatives. Similarly, papaverine N-oxide gave 1,2-dihydropapaverine as a major product accompanying with papaverine.