The Renaissance of Organo Nitriles in Organic Synthesis

Chemistry - An Asian Journal, Journal Year: 2022, Volume and Issue: 17(21)

Published: Sept. 1, 2022

In the arena of functional group-oriented organic synthesis, nitrile or cyano functionality is immense importance. The presence nucleophilic N-atom, π-coordinating ability triple bond, and electrophilic C-center imparts unique interesting reactivities. Owing to transform into various other groups intermediates, chemistry very rich diverse. particular, involvement in numerous reactions such as inter- intramolecular alkyne insertion, [2+2+2] cycloaddition with alkynes, [3+2] azides, [4+2] dienes allow synthesis many important carbo- heterocycles. Furthermore, serves a directing group C-H bond functionalization introduce diverse functionalities participate radical acceptor cascade strategies obtain large variety molecules. This review mainly focuses on reactivity synthetic application including functionalization, cycloaddition, thermal photochemical strategy. objective current aims at bringing out striking collection nitrile-triggered transformations.

Language: Английский

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Visible-light driven electron–donor–acceptor (EDA) complex-initiated synthesis of thio-functionalized pyridines

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(51), P. 7990 - 7993

Published: Jan. 1, 2023

A visible/solar-light-induced electron-donor-acceptor (EDA)-aggregated/mediated radical cyclization between (E)-2-(1,3-diarylallylidene)malononitriles and thiophenols leads to poly-functionalized pyridines. The two reacting partners form an EDA complex that absorbs light triggers the single-electron transfer (SET) generate a thiol radical, which undergoes addition/cyclization with dicyanodiene through formation of C-S C-N bonds.

Language: Английский

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Intrinsic mechanism of improving the anti-oxidation activity by increasing the molecular weight via alkyl chain grafted on p -phenylenediamine-based structure

Molecular Simulation, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 7

Published: March 10, 2025

Language: Английский

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Regioselective Access to 1,2,4-Triazole-Fused N-Heterocycle, Pyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, via Double Dehydrative Cyclizations

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(16), P. 11748 - 11761

Published: Aug. 1, 2023

A highly efficient and regioselective approach to a novel 1,2,4-triazole-fused N-heterocyclic scaffold, pyrrolo[1,2-a][1,2,4]triazolo[3,4-c]pyrazine, was established by base-promoted reaction of pyrrole-2-carbonitrile-derived substrate with acyl hydrazide where domino double ring closures comprised enamine formation, attack on nitrile, cyclodehydration enabled sequential construction pyrazine 1,2,4-triazole systems formation three C-N bonds.

Language: Английский

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Visible/solar-light-driven thiyl-radical-triggered synthesis of multi-substituted pyridines

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(8), P. 1680 - 1691

Published: Jan. 1, 2023

A light-triggered synthesis of thio-functionalized pyridines is demonstrated using γ-ketodinitriles, thiols, and eosin Y as the photocatalyst. The reaction proceeds via selective attack on one cyano groups by an in situ generated thiyl radical. also with nearly equal efficiency direct sunlight. Large-scale a few useful synthetic transformations substituted are performed.

Language: Английский

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Organic Base-Promoted C–N- and C–O-Coupled Domino Cyclization Strategy: Syntheses of Oxazine-6-ones and 4-Pyrimidinols

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5650 - 5664

Published: April 5, 2024

Oxazine-6-one and 4-pyrimidinol are two important frameworks in pharmaceutical production. Herein, we disclosed a simple, efficient, inexpensive organic base-promoted additive-stimulated protocol for the syntheses of variably functionalized oxazine-6-ones 4-pyrimidinols employing acetonitrile solvent under conventional heating conditions using an oil bath through C–N C–O coupled domino steps. This simple practicable productive utilizes easily producible cheap precursors, namely, benzimidates or benzamidines, with differently substituted dicyano-olefins, it comprises step economy, robustness, moisture insensitive affording high yield that avoids use transition-metal catalysts, multistep multicomponent strategy, harsh reaction involving hazardous chemicals. method is scalable into gram-scale production good yield.

Language: Английский

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Synthetic Approaches Toward Imidazo‐Fused Heterocycles: A Comprehensive Review

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 24, 2024

ABSTRACT Imidazole moiety when fused with other heterocyclic system form numerous compounds different types of pharmacological and biological activities. In this review, we discussed a comprehensive analysis the synthetic methodologies reaction mechanisms for imidazo‐fused molecules. These molecules represent crucial class due to their significant applications versatile chemical reactivity. This article meticulously examined various routes construction heterocycles, ranging from traditional methods modern approaches such as microwave‐assisted reactions, NPs‐catalyzed light‐mediated synthesis, electrochemical transition metal‐free synthesis routes. By consolidating current knowledge highlighting future directions, review aims serve treasure research community in fields organic chemistry, medicinal material science.

Language: Английский

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Transformable Transient Directing Group-Assisted C(sp²)–H Activation: Synthesis and Late-Stage Functionalizations of o-Alkenylanilines

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(19), P. 13383 - 13388

Published: Sept. 14, 2022

The isocyanate group in aryl isocyanates serves as a transformable transient directing Ru(II)-catalyzed ortho olefination leading to o-alkenylanilines. In alcoholic solvents, are transformed into carbamates, which initiate the insertion of acrylates via o-C-H activation. particular, tAmOH dual role solvent-cum mediator. o-alkenylanilines converted azacoumarins and subsequently C-4 aryl-substituted using iodides coupling partners Pd(II)-catalyzed C-H functionalizations.

Language: Английский

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Five-membered ring systems: with more than one N atom

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 255 - 304

Published: Jan. 1, 2023

Language: Английский

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Cu‐promoted Access to 1,4‐Diazine‐fused Isoindoles Through Concomitant Csp3‐N and Csp2‐N Bonds Formation Starting from Constrained N,O‐acetals

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(24), P. 5089 - 5099

Published: Aug. 28, 2024

Abstract Scarce dihydro‐1,4‐diazinoisoindole framework bearing two points of diversity was prepared through a cascade process based on concomitant C sp 3 − N and 2 bond formation. This approach consists an amidation in basic medium tosyl group by nucleophilic substitution followed Cu‐mediated Goldberg reaction the same operation. The required β‐bromoenamide obtained tosylation fused brominated N,O ‐acetals for first time acidic using submolar amounts PTSA. piperazines are useful building blocks as illustrated formation pentacyclic product via intramolecular interception enamide function.

Language: Английский

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