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

J Koyama, I TOYOKUNI, K Tagahara

Index: Koyama, Junko; Toyokuni, Izumi; Tagahara, Kiyoshi Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 2 p. 332 - 334

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Citation Number: 17

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.

 Related Synthetic Route

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