Reactions of 5-Hydroxymethyl-1H-indole-4,7-dione with Enamines for the First Construction of 1H,5H-Pyrano[3,4-f]indole-4,9-dione Derivatives
摘要:
5-Hydroxymethyl-1-methyl-2,3-diphenyl-IH-indole-4,7-dione (4) was synthesized and the tandem Michael addition/cyclization sequence between this indolequinone and enamines has been used to construct title pyranoindolequinone derivatives (6), (7), and (9).
Diels-Alder Reaction of 1,2,3-Benzotriazine with Enamine: Application to the Synthesis of Alkaloids, 2-Propylquinoline and 2-Pentylquinoline.
作者:Junko KOYAMA、Izumi TOYOKUNI、Kiyoshi TAGAHARA
DOI:10.1248/cpb.46.332
日期:——
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.
2-Acetyl-1,4-naphthoquinone was treated with pyrrolidine (or morpholine) enamines, derived from cyclic and acyclic ketones, in DMF at room temperature for 24-72 h to afford 3,4-disubstituted 1-pyrrolidino(or morpholino)-9,10-anthraquinones. On the other hand, when the treatment of 2-acetyl-1,4-naphthoquinone with enamines for 2 min was followed by addition of water and heating at 100 degrees C for 2 h, the corresponding 1-hydroxy-9,10-naphthoquinone derivatives were obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.