Diels-Alder reaction of 1,2,3-benzotriazine with enamine: Application to the synthesis of alkaloids, 2-propylquinoline and 2-pentylquinoline

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 2, 1998, Pages 332-334

  Koyama, Junko ^a   Toyokuni, Izumi ^a   Tagahara, Kiyoshi ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

1,2,3,4 tetrahydroacridine; 1,2,3 benzotriazine; 2 pentylquinoline; 2 propylquinoline; Diels Alder reaction; Quinoline derivative

Indexed keywords

1,2,3 BENZOTRIAZINE DERIVATIVE; 2 PENTYLQUINOLINE; 2 PROPYLQUINOLINE; ALKALOID; ENAMINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; SPECTROSCOPY; SYNTHESIS;

EID: 0031892142     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.332     Document Type: Article

References (19)

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18. The 2-pentanone enamine was prepared from 2-pentanone and pyrrolidine in benzene in the presence of p-toluenesulfonic acid for about 1 h. The Diels-Alder reaction of 1 and the above enamine gave 4k-1, but 4g could not be detected by TLC. The reaction of 2-heptanone enamine (reaction time: 1 h) and 1 gave only 4l-1. The preparation time of enamines (of 2-pentanone or 2-heptanone) was over 10 h, so that the Diels-Alder reaction of 1 and enamines gave 4k-1 or 4l-1 as the main product (30, 32%) and 4g or 4l-2 as the minor product (5, 9%). The Diels-Alder reaction of 3f and 1 gave only 4f whether the preparation time of enamine was short or long.
19. 3c) But the yields of the Diels-Alder reaction of 1 and the enamines of other carbonyl compounds were rather similar in the presence and in the absence of zinc bromide.