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Paper | Regular issue | Vol 27, No. 9, 1988, pp.2213-2217
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4634
The Effects of Solvent and Temperature on the Orientation of Cycloaddition Reaction of 1,2,3-Triazine Enamines: Its Application to the Synthesis of Alkaloids, Onychine and 6-Methoxyonychine

Teruyo Okatani,* Junko Koyama, Yukio Suzuta, and Kiyoshi Tagahara

*Kobe Women’s College of Pharmacy, Motoyamakita, Higashinad, Kobe, Hyogo 658, Japan

Abstract

4-Methyl-1,2,3-triazine was treated with several enamines in chloroform to afford 2,5,6-trisubstituted pyridines. In each case, cycloaddition occurs N-3/C-6 of the 1,2,3-triazine nucleus. On the other hand, when high boiling solvent was employed, cycloaddition took place involving the N-3/C-6 cycloadduct and N-1/C-4 cycloadduct. As application of synthetic method, we accomplished the synthesis of alkaloids, onychine and 6-methoxyonychine.