Journal ArticleDOI
Divergent reactions of indoles with aminobenzaldehydes: indole ring-opening vs. annulation and facile synthesis of neocryptolepine
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TLDR
Indoles display a diverse pattern of reactivity upon reaction with different classes of aminobenzaldehydes as discussed by the authors, showing that the acid-promoted reaction with secondary amnobenzaldehyde leads to indole annulation followed by spontaneous oxidation to neocryptolepine and analogues.Abstract:
Indoles display a diverse pattern of reactivity upon reaction with different classes of aminobenzaldehydes. Whereas the acid-promoted reaction with secondary aminobenzaldehyde leads to indole annulation followed by spontaneous oxidation to neocryptolepine and analogues, the reaction with primary aminobenzaldehydes results in the formation of synthetically useful quinolinesvia a remarkably facile indole ring-opening.read more
Citations
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Advances in dearomatization strategies of indoles
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Access to Structurally Diverse Quinoline-Fused Heterocycles via Rhodium(III)-Catalyzed C-C/C-N Coupling of Bifunctional Substrates.
TL;DR: Rhodium(III)-catalyzed C-H activation of heteroarenes and functionalization with bifunctional substrates such as anthranils allows facile construction of quinoline-fused heterocycles under redox-neutral conditions.
Journal ArticleDOI
Redox-neutral α-oxygenation of amines: reaction development and elucidation of the mechanism.
Matthew T. Richers,Martin Breugst,Martin Breugst,Alena Yu. Platonova,Alena Yu. Platonova,Anja Ullrich,Anja Ullrich,Arne Dieckmann,Kendall N. Houk,Daniel Seidel +9 more
TL;DR: This overall redox-neutral amine α-C–H functionalization features a combined reductive N-alkylation/oxidative α-functionalization and is catalyzed by acetic acid, in contrast to previous reports.
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Tandem Rh(III)-Catalyzed C-H Amination/Annulation Reactions: Synthesis of Indoloquinoline Derivatives in Water.
Liangliang Shi,Baiquan Wang +1 more
TL;DR: An efficient Rh(III)-catalyzed synthetic method for indoloquinoline derivatives from readily available indoles and isoxazoles was developed and a catalytically competent five-membered rhodacycle has been isolated and characterized, thus revealing a key intermediate in the catalytic cycle.
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Redox-Neutral Copper (II) Carboxylate Catalyzed α-Alkynylation of Amines
TL;DR: A new strategy for iminium ion isomerization was applied to the direct, redox-neutral α-alkynylation of amines in Cu(II) 2-ethylhexanoate as the optimal catalyst for this three-component coupling reaction of secondary amines, aldehydes and alkynes.
References
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Journal ArticleDOI
Practical methodologies for the synthesis of indoles.
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Synthesis and functionalization of indoles through palladium-catalyzed reactions
Sandro Cacchi,Giancarlo Fabrizi +1 more
TL;DR: P palladium-catalyzed synthesis can provide access to fine chemicals, agrochemical and pharmaceutical intermediates, and active ingredients in fewer steps and with less waste than classical.
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Marine indole alkaloids: potential new drug leads for the control of depression and anxiety
TL;DR: Information is provided on current and potential pharmaceuticals including small molecule natural indole alkaloids to their biological properties, structure-activity relationship studies, and especially their potential for the treatment of neurological disorders, including depression.
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Privileged Scaffolds for Library Design and Drug Discovery
TL;DR: This review explores the concept of using privileged scaffolds to identify biologically active compounds through building chemical libraries by revealing through four selected examples the present state of the art in privileged scaffold library synthesis.