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Paper | Regular issue | Vol 29, No. 9, 1989, pp.1809-1814
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5054
Modified Synthesis of Monocyclic 1,2,3-Triazine and Cycloaddition Reaction with Enamine: The Application to the Synthesis of Alkaloids, Tortuosamine, N-Formyltortuosamine and N-Acetyltortuosamine

Teruyo Okatani,* Junko Koyama, and Kiyoshi Tagahara

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


Monocyclic 1,2,3-triazines were obtained by periodate oxidation of 1-aminopyrazoles in good reproducibilities and yields. The Diels-Alder reaction of 1,2,3-triazine with several enamines was carried out to afford 2,3-disubstituted pyridines. As an application of this method, we accomplished the synthesis of alkaloids, tortuosamine, N-formyltortuosamine and N-acetyltortuosamine.