Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones

Tetrahedron Letters, Год журнала: 2023, Номер 130, С. 154766 - 154766

Опубликована: Сен. 26, 2023

Язык: Английский

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[4 + 2] Cyclization or Lossen Rearrangement: Rhodium-Catalyzed Divergent Synthesis of Carboline Derivatives with Anticancer Activity

Organic Letters, Год журнала: 2024, Номер 26(20), С. 4212 - 4217

Опубликована: Май 14, 2024

An unusual rhodium-catalyzed C–H activation/Lossen rearrangement/oxa-Michael addition tandem cyclization has been achieved along with a tunable well-known activation/[4 + 2] annulation, leading to regio-, chemo-, and diastereoselective access diverse pentacyclic α-carbolines β-carboline-1-one derivatives in moderate good yields significant anticancer activity.

Язык: Английский

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Lewis‐Base Dependent (3+3) Annulations of Acetoxy Allenoates with Iminoindolines: α‐Carboline Scaffolds with Varied Substituents

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(24), С. 4316 - 4332

Опубликована: Ноя. 12, 2022

Abstract Lewis base dependent (3+3) annulations of β′ / δ ‐acetoxy allenoates with iminoindolines offer α ‐carbolines varying substituents depending on the used as well subtle changes in reaction conditions. The phosphine‐catalyzed annulation δ‐ acetoxy involves 6‐ exo‐trig cyclization, tosyl anion elimination/trapping, and ethyl acetate elimination key steps delivering β ‐H γ ‐tosyl containing ‐carbolines. An unobvious (by C ‐C bond cleavage) −CH 2 CO Et moiety is observed here. same reactants under DBU catalysis that retain but are devoid −Ts group via 6‐exo‐dig cyclization. β′‐ allenoate completely tertiary amine dependent; use DABCO affords tetrahydro‐ exclusively excellent stereoselectivity while offers substituted distinct from those using DABCO. Several control experiments HRMS studies have been done support a plausible mechanism. magnified image

Язык: Английский

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Carboline Regioisomers Based on Unified Synthetic Approaches

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(13), С. 2126 - 2146

Опубликована: Май 31, 2023

Abstract Carbolines are a prominent class of tricyclic alkaloids omnipresent in natural products and bioactive compounds. Four different carboline regioisomers known (α‐, β‐, γ‐, δ‐carbolines), which can be classified according to the nitrogen atom position inside pyridine ring. As an emerging structural motif drug discovery, multitude synthetic methods have been established for construction frameworks, general requires customized approaches assembly each regioisomer. Distinguishingly, their frameworks also accessible from unified approaches, capable generating multiple regioisomers, thus suitable introducing diversity isomeric carbolines. In this review, carbolines based on is summarized.

Язык: Английский

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Recent Strategies in Transition-Metal-Catalyzed Sequential C–H Activation/Annulation for One-Step Construction of Functionalized Indazole Derivatives

Molecules, Год журнала: 2022, Номер 27(15), С. 4942 - 4942

Опубликована: Авг. 3, 2022

Designing new synthetic strategies for indazoles is a prominent topic in contemporary research. The transition-metal-catalyzed C-H activation/annulation sequence has arisen as favorable tool to construct functionalized indazole derivatives with improved tolerance medicinal applications, functional flexibility, and structural complexity. In the current review article, we aim outline summarize most common protocols use synthesis of target via one-step derivatives. We categorized text according metal salts used reactions. Some were catalysts, others may have been oxidants and/or activation precatalysts. roles some corresponding reaction mechanisms not identified. It can be expected that synopsis will provide accessible practical guidance colleagues interested subject.

Язык: Английский

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Novel access to α-carbolines with biological applications

European Journal of Medicinal Chemistry, Год журнала: 2024, Номер 276, С. 116700 - 116700

Опубликована: Июль 20, 2024

Язык: Английский

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Easy one-pot synthesis of multifunctionalized indole–pyrrole hybrids as a new class of antileishmanial agents

RSC Advances, Год журнала: 2024, Номер 14(22), С. 15713 - 15720

Опубликована: Янв. 1, 2024

A chemoselective one-pot synthesis of indole–pyrrole hybrids has been developed. The new were phenotypically screened for efficacy against L. infantum promastigotes. Compound 3d was the most active with IC 50 = 9.6 μM and a selectivity index 5.

Язык: Английский

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