Indole frameworks via transition-metal-free annulation: a current perspective

New Journal of Chemistry, Год журнала: 2023, Номер 47(29), С. 13729 - 13775

Опубликована: Янв. 1, 2023

The present review summarizes recent (2019–mid-2023) efforts towards the construction of indole core via transition-metal-free methods.

Язык: Английский

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Indoles in Drug Design and Medicinal Chemistry

European Journal of Medicinal Chemistry Reports, Год журнала: 2025, Номер unknown, С. 100252 - 100252

Опубликована: Фев. 1, 2025

Язык: Английский

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Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis

Molecules, Год журнала: 2022, Номер 27(19), С. 6708 - 6708

Опубликована: Окт. 9, 2022

Many heterocyclic compounds can be synthetized using diaza-1,3-butadienes (DADs) as key structural precursors. Isolated and in situ diaza-1,3-butadienes, produced from their respective precursors (typically imines hydrazones) under a variety of conditions, both react with wide range substrates many kinds reactions. Most these reactions discussed here include nucleophilic additions, Michael-type reactions, cycloadditions, Diels–Alder, inverse electron demand aza-Diels–Alder This review focuses on the reports during last 10 years employing 1,2-diaza-, 1,3-diaza-, 2,3-diaza-, 1,4-diaza-1,3-butadienes intermediates to synthesize heterocycles such indole, pyrazole, 1,2,3-triazole, imidazoline, pyrimidinone, pyrazoline, -lactam, imidazolidine, among others. Fused heterocycles, quinazoline, isoquinoline, dihydroquinoxaline derivatives, are also included review.

Язык: Английский

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Easy Access to Indole‐based Bi‐Sulfurylate‐Heterocyclic Scaffolds

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 11(9)

Опубликована: Июнь 9, 2022

Abstract New and valuable indole based sulfurylated bi‐heterocyclic systems such as 4‐((1 H ‐indol‐2‐yl)thio)‐5‐oxo‐4,5‐dihydro‐1 ‐pyrazoles 3,3‐dimethyl‐3′ ‐spiro‐indoline‐2,2′‐thiazoles are regioselectively obtained under very mild conditions employing 1,2‐diaza‐1,3‐dienes not smelly indoline 2‐thiones starting materials.

Язык: Английский

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Straightforward Access to Pyrazine‐(2,3)‐diones through Sequential Three‐Component Reaction

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(6)

Опубликована: Янв. 13, 2023

Abstract A novel protocol for the assembly of polysubstituted 2,3‐dioxo‐1,4,5,6‐tetrahydropyrazines and 2,3‐dioxo‐hydro‐1 H ‐cycloalkyl[ b ]pyrazines has been developed by sequential three‐component reaction primary aliphatic amines, 1,2‐diaza‐1,3‐dienes (DDs) oxalyl chloride. This synthetic sequence proceeds initial aza‐Michael addition amine to azo‐ene compounds subsequent ring closure involving The ready availability starting materials as well high level practicability work‐up make this approach an attractive opportunity towards these uncommon systems.

Язык: Английский

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FeCl₃‐Catalyzed Formal [3+2] Cyclodimerization of 4‐Carbonyl‐1,2‐diaza‐1,3‐dienes

European Journal of Organic Chemistry, Год журнала: 2021, Номер 2021(37), С. 5202 - 5208

Опубликована: Сен. 7, 2021

Abstract Substituted 1‐aminopyrroles are easily accessible by iron‐catalyzed cascade reaction of 1,2‐diaza‐1,3‐dienes. Mechanistically, a formal [3+2] cyclodimerization is hypothesized to proceed through [4+2] 4‐substitued 1,2‐diaza‐1,3‐dienes followed intramolecular ring closure fused diaziridin‐pyrrolines which successively opened undergo contraction process and consequently generate the desired pyrrole moiety. The presence activated hydrogen in terminal position azo‐enic moiety crucial for synthesis pyrroles.

Язык: Английский

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Experimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones

Molecules, Год журнала: 2021, Номер 26(21), С. 6557 - 6557

Опубликована: Окт. 29, 2021

Here we report the synthesis of interesting 3-alkyl-4-hydroxy-1-aryl-4-(propa-1,2-dienyl)1

Язык: Английский

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1,2‐Diaza‐1,3‐dienes as a Multifaceted Synthon for the Synthesis of Heterocycles: A Fifteen‐Years Update

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(44)

Опубликована: Авг. 9, 2024

Abstract The discovery of structurally unique scaffolds entities with increased complexity and balanced physicochemical properties has the potential to allow synthetic chemists exploit areas chemical space that were previously inaccessible. Among different strategies employed for generating N ‐heterocycles, cyclization cycloaddition reactions represent a valuable tool. purpose this minireview is summarize recent advances (2009‐present) from our laboratory on generation intriguing five‐, six‐ seven‐membered mono‐ or poly‐heterocyclic architectures (linear, fused spiro) employing 1,2‐diaza‐1,3‐dienes (DDs) as key synthons.

Язык: Английский

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Chemo- and regioselective oxidation of substituted 2,3,4,9-tetrahydro-1H-carbazoles

Chemistry of Heterocyclic Compounds, Год журнала: 2022, Номер 58(8-9), С. 403 - 411

Опубликована: Сен. 1, 2022

Язык: Английский

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