TBAI‐Promoted Electrochemical Cyclization: Synthesis of Quinazolines Using Cascade C—N Bond Generation

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(1)

Published: Jan. 1, 2025

Abstract An electrochemical cyclization strategy is employed herewith for the eco‐friendly and cost‐effective synthesis of 2‐substituted quinazolines by using 2‐aminobenzylamines aldehydes or alcohols as starting substrates. The reactions were conducted under two distinct reaction temperatures: 25 °C 60 alcohols. Tetra‐ n ‐butylammonium iodide (TBAI) participates in dual roles such as, an electrolyte a mild reagent to facilitate formation at constant current 30 mA graphite electrode anode platinum cathode dimethyl sulfoxide (DMSO) solvent. Under devised process, accomplished with broad substrate scope excellent yields (up 90%), which reduces toxic side products. plausible mechanistic pathways have been formulated, are supported control experiments cyclic voltammetry studies. findings demonstrate that conditions, iodonium ions generated, play crucial role enhancing efficacy described method.

Language: Английский

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Electrochemical Cyclization–Desulfurization Approach for the Synthesis of 1,3-Benzoxazines Using Cascade C–O and C–N Bond Formation

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 29, 2025

A cost-effective, eco-friendly, and highly efficient one-pot electrochemical process has been described for the synthesis of 4H-1,3-benzoxazine 4,5-dihydro-1,3-benzoxazepine derivatives by employing 2-aminobenzyl alcohols, 2-(2-aminophenyl)ethan-1-ol, isothiocyanate derivatives, TBAPF6 as an electrolyte. The developed method is accomplished at 25 °C with a constant current 20 mA. Utilizing graphite anode platinum cathode in dimethyl sulfoxide solvent, devised metal-free approach minimizes production waste eliminates need external oxidizing agents. Furthermore, these valuable molecules significantly enhances ongoing trends synthetic organic chemistry.

Language: Английский

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Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(47)

Published: Dec. 13, 2023

Abstract Nitrogen‐containing heterocycles such as imidazoles, thiazoles, and oxazoles play a significant role in the fields of biological pharmaceutical chemistry. These compounds were widely used for agrochemical, pesticide, medicinal, industrial applications. Due to wide spectrum structural diversity well activity N ‐heterocycles, plethora reports on their synthesis have appeared last few decades. However, developments various bond‐forming strategies C−C, C−N, C−O, C−S, N−N, C−H activation, been powerful synthetic tool derive copious ‐heterocycles. The most prominent fascinating imidazole, thiazole, oxazoles, benzimidazole moieties by C−C C−N coupling reactions, multi‐component cycloaddition etc. are discussed this study. studies demonstrated enormous potential methods accelerating modern chemical establishing molecular beauty through bonding. aspects methodologies, like optimized conditions, substrate scope, mechanistic investigations, detail.

Language: Английский

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Masters of Mediation: MN(SiMe₃)₂ in Functionalization of C(sp³)−H Latent Nucleophiles

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(29)

Published: March 18, 2024

Abstract Organoalkali compounds have undergone a far‐reaching transformation being coupling partner to mediator in unusual organic conversions which finds its spot the field of sustainable synthesis. Transition‐metal catalysis has always been priority C( sp 3 )−H bond functionalization, however alternatively, recent times this seriously challenged by earth‐abundant alkali metals and their complexes arriving at new organometallic reagents. In line, importance MN(SiMe ) 2 (M=Li, Na, K & Cs) reagent revived functionalization over years synthesis is showcased minireview. with higher reactivity, enhanced stability, bespoke cation‐π interaction shown eye‐opening mediated processes such as )−C( cross‐coupling, radical‐radical aminobenzylation, annulation, aroylation, other transformations utilize readily available petrochemical feedstocks. This article also emphasizes reactivity unreactive robust C−X (X=O, N, F, C) cleavage reactions that occurred alongside functionalization. Overall, review encourages community exploit untapped potential inspires them take up subject even greater heights.

Language: Английский

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Skeletal Editing Through Single Atom Insertion and Transmutation: An Insight into A New Era of Synthetic Organic Chemistry

Synthesis, Journal Year: 2024, Volume and Issue: 56(24), P. 3793 - 3814

Published: Aug. 20, 2024

Abstract Considering the importance of heterocycles, significantly represented in medicinal chemistry and drug development, single-atom insertion technique transmutation strategy provide productive approaches towards complicated molecular structures through heterocycle diversification. It shows a potentially powerful approach for modifying complex substrates concisely chemospecifically. Although skeletal editing applies to cyclic acyclic compounds, this review focuses on diversification carbo- heterocyclic compounds synthesizing various medicinally important molecules via technique. The classification system is based recent critical historical methods as applied aromatic rings. 1 Introduction 2 Skeletal Editing Carbon-Atom Insertion 2.1 Indoles Pyrroles Derivatives: into C=C Bond 2.2 Pyrazole Indazole an N–N 2.3 CF3 Group Heteroarenes 2.4 Imidazole C–N 2.5 Atom-to-Atom Transmutation 3 N-Atom 3.1 Nitrogen-Atom Carbocycles 3.2 Heterocycles 3.3 Carbon Nitrogen Molecular Isotopic 4 Conclusion

Language: Английский

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A Metal‐Free KO^tBu‐Mediated Protocol towards the Synthesis of Quinolines, Indenoquinolines and Acridines

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(4)

Published: Jan. 23, 2024

Abstract An expeditious strategy has been developed for the synthesis of diverse quinolines, indenoquinolines and acridines using KO t Bu‐mediated reaction conditions. The designed process utilizes 2‐aminoaryl carbaldehydes/2‐aminoaryl ketones methyl/methylene group containing as readily available feedstock. chemical transformation was affected at room temperature within a short duration time to obtain N ‐heterocycles yields up 92 %. established also exhibits considerable functional tolerance with an operational simplicity.

Language: Английский

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Desymmetric [3+3] Cyclization of p-Quinamines for the Synthesis of 1,2,4-Oxadiazines and Hydroquinoxalines

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1770 - 1774

Published: Feb. 14, 2024

General and efficient strategies for highly diastereoselective synthesis of divergent heterocyclic scaffolds through desymmetric [3+3] cycloaddition p-quinamines with 1,3-dipole surrogates hydroximoyl halides α-halohydroxamates have been developed. This synthetic protocol provided a variety architectures containing 1,2,4-oxadiazine hydroquinoxaline skeletons in good yields wide substrate scope.

Language: Английский

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Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(3)

Published: Jan. 17, 2024

Abstract Organic synthesis involves the production of important chemical structures using scalable and cost‐effective methods that are also environmentally friendly. In this review, a detailed analysis use iodine DMSO in various synthetic routes for preparation valuable targets presented. These reduce acceptance on expensive additives reagents, offer more sustainable solution these scaffolds.

Language: Английский

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ortho-Halobenzyl Halides as Precursors for the Synthesis of Five- to Nine-Membered Ring Structures Employing Transition Metals as Catalysts

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: April 22, 2024

Abstract This review highlights the multifaceted usefulness of o-halobenzyl halides as pivotal substrates for construction five- to nine-membered cyclic structures with aid transition metals catalysts. These privileged entities engage dual active sites, enabling combination both intermolecular benzylation and intramolecular arylation strategies that directs formation a diverse repository structures. The introduction transition-metal catalysis in cross-coupling transformations sparked revolution forging aryl–heteroatom bonds, culminating evolution more potent methodologies synthesis wide spectrum valuable compounds. Furthermore, associated pharmaceutical biological attributes these augment their significance medicinal chemistry research. aims showcase importance this synthetic methodology its far-reaching applications synthesis. 1 Introduction 2 Synthesis Five-Membered Rings 3 Six-Membered 4 Seven-Membered 5 Eight- Nine-Membered 6 Conclusion

Language: Английский

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Alkali Metal-Ion Binding by a Model Macrocycle Containing a C-I···N Halogen Bonded Network: A DFT Study of C-I···M+ and N···M+ Binding Interactions, M+ = Li+, Na+, K+, and Rb+

Inorganics, Journal Year: 2024, Volume and Issue: 12(6), P. 161 - 161

Published: June 6, 2024

The complexation of an alkali metal ion by a model macrocycle is examined using the M05-2X/DGDZVP DFT method. built connecting three cyclopenta[b]pyrrole motifs with alternating acetylene and ethylene linkages. Replacing one C-H bonds in each motif C-I bond allows for formation intramolecular C-I···N halogen bonds. Two distinct binding modes were found ion. In mode, occurs solely iodine atoms, via I···M+ interactions, while maintaining integrity energies are range −66 to −35 kcal/mol. other includes nitrogen atom as well, −71 −38 this network weakened. presence strength interactions further AIM NBO calculations. Lastly, geometries transition state structures linking less stable more complexes obtained, their calculated Gibbs free energy barriers 1.6 1.9

Language: Английский

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