Diels-Alder Reaction of 1, 2, 3-Benzotriazine with Enamine : Application to the Synthesis of Alkaloids, 2-Propylquinoline and 2-Pentylquinoline

Junko KOYAMA; Izumi TOYOKUNI; Kiyoshi TAGAHARA

doi:10.1248/cpb.46.332

Junko KOYAMA, Izumi TOYOKUNI, Kiyoshi TAGAHARA

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Keywords: Diels-Alder reaction, 1, 2, 3-benzotriazine, quinoline derivative, 1, 2, 3, 4-tetrahydroacridine, 2-propylquinoline, 2-pentylquinoline

JOURNAL FREE ACCESS

1998 Volume 46 Issue 2 Pages 332-334

DOI https://doi.org/10.1248/cpb.46.332

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Abstract

The Diels-Alder reaction of 1, 2, 3-benzotriazine with several pyrrolidine enamines of carbonyl compounds was carried out in chloroform in the presence of zinc bromide to afford 2- or 3-mono-, or 2, 3-disubstituted quinolines. This method was applied to the synthesis of the alkaloids, 2-propylquinoline and 2-pentylquinoline.

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