Journal ArticleDOI
Cyclizaticn of 3-formyl-2-acetylenylindole oximes
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TLDR
3-Formyl-2-acetylenyl-1-methylindole oximes readily undergo intramolecular heterocyclization with closure of a pyridine ring and formation of substitutedγ-carboline N-oxides as discussed by the authors.Abstract:
3-Formyl-2-acetylenyl-1-methylindole oximes readily undergo intramolecular heterocyclization with closure of a pyridine ring and formation of substitutedγ-carboline N-oxides.read more
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Journal ArticleDOI
Synthesis of β- and γ-Carbolines by the Palladium/Copper-Catalyzed Coupling and Cyclization of Terminal Acetylenes
Haiming Zhang,Richard C. Larock +1 more
TL;DR: In this article, a variety of 3-substituted β- and γ-carbolines have been synthesized from 3-iodoindole-2-carboxaldehydes and 2-bromoindoles-3-carboardaldehyde, respectively, using PdCl2(PPh3)/CuI as the catalyst.
Journal ArticleDOI
Synthesis of Annulated γ-Carbolines and Heteropolycycles by the Palladium-Catalyzed Intramolecular Annulation of Alkynes
Haiming Zhang,Richard C. Larock +1 more
TL;DR: A variety of N-substituted 2-bromo-1H-indole-3-carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, subjected to palladium-catalyzed intramolecular iminoannulation, affording various gamma-carboline derivatives with an additional ring fused across the 4- and 5-positions in good to excellent yields.
Journal ArticleDOI
Rapid access to amino-substituted quinoline, (di)benzofuran, and carbazole heterocycles through an aminobenzannulation reaction.
Martin Tiano,Philippe Belmont +1 more
TL;DR: An interesting range of disubstituted quinolines, dibenzofurans, and carbazoles are obtained along with enamine formation in some cases, which differs from classical heterocyclic methods which go through closure at the heteroatom-containing ring instead of benzene ring formation.
Journal ArticleDOI
Synthesis of β- and γ-carbolines by the palladium/copper-catalyzed coupling and copper-catalyzed or thermal cyclization of terminal acetylenes
Haiming Zhang,Richard C. Larock +1 more
TL;DR: In this paper, a variety of 3-substituted β- and γ-carbolines have been synthesized from 3-iodoindole-2carboxaldehydes and 2-bromoindoles-3-carboxldehydes, respectively.
Journal ArticleDOI
Synthesis of annulated gamma-carbolines by palladium-catalyzed intramolecular iminoannulation.
Haiming Zhang,Richard C. Larock +1 more
TL;DR: In this paper, a variety of N-substituted 2-bromo-1H-indole-3 carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, which have been subjected to palladium-catalyzed intramolecular iminoannulation, affording various annulated γ-carbolines in excellent yields.
References
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Journal ArticleDOI
The reactions of 2-alkynylbenzaldehydes with hydrazides: a route to isoquinoline N-imines
TL;DR: In this article, the authors proposed a nucleophilic attack on the alkyne bond of 2-ethynylbenzaldehyde to give Isoquinoline N-imines in moderate yield.
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