Indole, 6. Mitt. Lactamisierung von 4,9‐Dihydropyrano[3,4‐b]indol‐1(3H)‐onen mit Methylamin. – Ein neuer Syntheseweg zu Strychnocarpin und seinen Derivaten

Abstract

Stry chnocarpin-S y nthese 411 Indole, 6. Mitt. ' ) Lactamisierung von 4,9-Dihydropyrano[3,4-b]indol-1( 3H)-onen mitMethylamin. -Ein neuer Syntheseweg zu Strychnocarpin und seinen Die Lactamisierung der sowohl aus 1 als auch aus 2 zuganglichen Pyranoindolone 3a-g stellt eine einfache Synthese von Strychnocarpin (4a) und seinen substituierten Derivaten 4b-g, 5b, c dar. Die Reduktion fuhrt zu den Tetrahydro-P-carbolinen 6a-d, f, h.Arch. Pharm. (Weinheim) 321,411-414 (1988) 0 VCH Verlagsgesellschafl mbH, 0 -6 9 4 0 Weinheim. 1988 0365-6233/88/0707-0411 $02.50/0

Pd/Cu Cocatalyzed Oxidative Tandem C–H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones

“…2l was synthesized according to general procedure A from 1l (0.2 mmol, 37.8 mg). The title compound was isolated as a light yellow solid (24.4 mg, 57% yield) …”

“…The title compound was isolated as a light yellow solid (24.4 mg, 57% yield). 34 R f (petroleum ether/EtOAc 2:1): 0.3; 1 H NMR (400 MHz, DMSO-d 6 ) δ 11.44 (brs, 1H), 7. 34 (s,1H),7.26 (d,J = 8.4 Hz,1H),7.03 (d,J = 8.4 Hz, 1H), 3.64 (t, J = 8.0 Hz, 2H), 2.99 (s, 3H), 2.96 (t, J = 6.8 Hz, 2H), 2.37 (s, 3H); HRMS(ESI) calcd for C 13 H 15 N 2 O (M+H) + 215.1179+ 215. , found 215.1177indol-1-one 2m.…”

New IndoleN-Oxide Alkaloids fromEvodia fargesii

“…Up to now, few phytochemical studies on this plant have been reported, with the exception of the essential oil analysis of its seeds [1]. Due to our continuing interest in the genus Evodia [2], [3], [4], we conducted an investigation of the chemical constituents of the title plant, leading to the isolation of three novel indole N-oxide alkaloids, fargesine (1), plectocomine 12-methyl-5-O-b-D-glucopyranoside N 12 -oxide (2) and bufotenine 5-O-b-D-glucopyranoside N 12 -oxide (3), together with five known compounds: 10,11,12,13-tetrahydro-b-carboline (4) [5], N,N-dimethyltryptamine (5) [6], bufotenine (6) [7], N,N-dimethyltryptamine N 12 oxide (7) [8], and bufotenine N 12 -oxide (8) [9]. In the present paper, we describe the isolation and structural elucidation of these new compounds (Fig.…”