Synthesis of 3-(indol-2-yl)-propenoate derivatives of tryptamine, valuable intermediates for the preparation of indole alkaloids

PD Bailey, SP Hollinshead - Tetrahedron letters, 1987 - Elsevier
Tetrahedron Letters,Vol.28,No.25,pp 2879-2882,1987 0040-4039/87 $3.00 + .OO Printed in
Great Britain Pergamon Journals Ltd. SYNT Page 1 Tetrahedron Letters,Vol.28,No.25,pp …

A direct synthesis of 3-(pyrrolidin-3-yl) indoles for use as conformationally restricted analogs of tryptamines

JE Macor, DH Blank, K Ryan, RJ Post - Synthesis, 1997 - thieme-connect.com
An efficient, two step synthesis of 3-(pyrrolidin-3-yl) indoles 4 is described. Indoles react with
maleimides in refluxing acetic acid affording 3-(indol-3-yl) succinimides 6. Reaction times …

C (2)-Functionalized tryptophans from 3-acetoxyindoles and their possible implication in indole alkaloid biosynthesis

R Plate, AWG Theunisse… - The Journal of Organic …, 1987 - ACS Publications
The acetoxyindoles 10 and 11 are efficiently converted (85-95%) into the dihydro-1, 2-
oxazines 13 and 14, respectively, by reaction with the transient nitroso olefin 2, prepared in …

Chemistry of the Hexahydropyrrolo[2,3-b]indoles:  Configuration, Conformation, Reactivity, and Applications in Synthesis

D Crich, A Banerjee - Accounts of chemical research, 2007 - ACS Publications
The stereoselective formation of 2-endo-substituted hexahydropyrrolo [2, 3-b] indoles from 2-
substituted tryptamine derivatives, especially tryptophan, is discussed. Parallels are drawn …

Efficient synthesis of tryptamine

S Takano, T Nishimura, K Ogasawara - Heterocycles, 1977 - chemistry.mdma.ch
Of various methods available 1, the decarboxylation of tryptophan (1) is the simplest way to
the synthesis of tryptamine (3) which is a very important starting material in the synthesis of …

Synthesis of a conformationally restricted Tryptamine analog via an improved reduction of a derivative of Uhle's Ketone

EW Taylor - Synthetic Communications, 1989 - Taylor & Francis
Synthesis of a Conformationally Restricted Tryptamine Analog via an Improved Reduction of a
Derivative of Uhle's Ketone Page 1 SYNTHETIC COMMUNICATIONS, 19(3&4), 369-372 …

Synthesis and reactions of N-indol-3-ylmethylalkylammes and related compounds

ESM Afsah, AH Jackson - Journal of the Chemical Society, Perkin …, 1984 - pubs.rsc.org
A series of new N-indol-3-ylmethylalkylamines (1) have been synthesized in excellent yields
via transamination between gramine and the appropriate primary alkylamine. The use of …

Synthetic studies on indole alkaloids. VII. Effect of the piperidine ring substitution on intramolecular KtBuO/BF3. Et2O cyclization of N-(2-hydroxyethyl)-2-[1 …

A Diez, C Villa, M Rubiralta - Tetrahedron, 1993 - Elsevier
3, 3-Disubstituted N-(2-hydroxyethyl)-2-[1-(phenylsulfonyl)-3-indolyl]-piperidine 4 shows a
particular reactivity in front of KtBuO/BF3. Et2O: the intermediate spiroindolenine 15 evolves …

Electrophilic substitution in indoles—II: The formation of 3, 3-spirocyclic indole derivatives from tryptamines and their rearrangement to β-carbolines

AH Jackson, AE Smith - Tetrahedron, 1968 - Elsevier
Attempts to isolate 3, 3-spiro-cyclicindolenines thought to be intermediates in the cyclization
of benzylidenetryptamines to tetrahydro-β-carbolines are described. One such spiro …

Novel Products from Bischler-Napieralski Reaction of Arylacetyl-Tryptophan Esters. Synthesis of Spiropentacyclic Indolines Structurally Related to Indole Alkaloids

KM Biswas, RN Dhara, S Halder, H Mallik… - Synthetic …, 1993 - Taylor & Francis
Novel Products from Bischler-Napieralski Reaction of Arylacetyl-Tryptophan Esters. Synthesis of
Spiropentacyclic Indolines Struc Page 1 SYNTHETIC COMMUNICATIONS, 23(3), 379-388 (1993) …