Facile approach to multifunctionalized 5-alkylidene-3-pyrrolin-2-ones via regioselective oxidative cyclization of 2,4-pentanediones with primary amines and sodium sulfinates

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(15), С. 4078 - 4084

Опубликована: Янв. 1, 2022

Highly functionalized 5-alkylidene-3-pyrrolin-2-ones were efficiently synthesized via a four-component cascade cyclization/sulfonylation reaction between readily available 2,4-pentanediones, primary amines and sodium sulfinates under mild conditions.

Язык: Английский

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Synthesis of 4-Alkylated 1,4-Dihydropyridines: Fe(II)-Mediated Oxidative Cascade Cyclization Reaction of Cyclic Ethers with Enaminones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 11627 - 11636

Опубликована: Авг. 9, 2023

Syntheses of highly functionalized 4-alkylated 1,4-dihydropyridines (1,4-DHPs) from cyclic ethers and enaminones via iron(II)-mediated oxidative free radical cascade C(sp3)-H bond functionalization/C(sp3)-O cleavage/cyclization reaction have been first developed. This novel synthetic strategy offers an alternative method for the construction 1,4-DHPs by using esters as C4 sources, well expands application in heterocycle synthesis.

Язык: Английский

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Copper(II)‐Mediated Intermolecular Radical [3+2]‐Annulation of N,N‐Dimethyl Enaminones: Direct Access to 5‐Acyl‐3‐Furancarboxaldehydes

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(18), С. 4354 - 4359

Опубликована: Июль 26, 2021

Abstract Copper(II)‐mediated unprecedented intermolecular radical [3+2] annulation of N , ‐dimethyl enaminones has been developed. The protocol is promoted simply by copper(II) chloride to access 5‐acyl‐3‐furancarboxaldehydes with acceptable good yields and broad substrate scope. This reaction allows the formation multiple new bonds, including C( sp 2 )−O bond between two nucleophilic sites, )−C( ) C=O bond, through a cyclization process. Moreover, gram‐synthesis application research show potential value this transformation in industry. magnified image

Язык: Английский

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Base-Promoted [4 + 1 + 1] Multicomponent Tandem Cycloaddition of Ortho-Substituted Nitroarenes, Aldehydes, and Ammonium Salts To Access 2,4-Substituted Quinazoline Frameworks

The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(5), С. 1982 - 1995

Опубликована: Янв. 23, 2025

We report a base-promoted, metal-free multicomponent tandem reaction, involving [4 + 1 1] cycloaddition process between ortho-substituted nitroarenes, aldehydes, and ammonium salts. Modifying the substituents on nitroaromatic compounds effectively provides structurally diverse 2-substituted 4-alkenylquinazolines with good to excellent yields (77%-90% quinazoline 51 examples) high tolerance for various inorganic salts (13 examples, such as NH3·H2O, NH4Cl, NH4HF2). A new method constructing 2,4-substituted selectivity from simple nitrogen source was developed, reaction can be scaled up gram scale. Additionally, this also facilitates preparation of organic molecules photophysical properties, offering insights into further transformation quinazolines.

Язык: Английский

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Photocatalytic Three-Component Assemblies of Enaminones, α-Diazo Esters, and Nitriles for the Synthesis of N,N-Diacylated Glycine Esters

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 21, 2025

A facile method with simple starting materials, including enaminones, α-diazo esters, and nitriles, has been developed for the direct synthesis of N,N-diacyl glycine esters via visible light photocatalysis. The reaction involves a novel carbon-carbon bond cleavage in leading to products high tolerance variability substructures among all three components.

Язык: Английский

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Chemoselective synthesis of α-carboline derivatives via hypervalent iodine-catalyzed [3+3] annulation under metal-free conditions

Green Synthesis and Catalysis, Год журнала: 2023, Номер 5(2), С. 112 - 116

Опубликована: Янв. 5, 2023

A strategy for the synthesis of α-carboline derivatives from indole-3-carboxaldehydes and 3-aminocyclohex-2-enones under metal-free conditions has been developed. The combination use phenyliodine (III) diacetate (PIDA) benzoic acid could significantly facilitate corresponding [3 ​+ ​3] annulation process. This newly developed featured unextraordinary chemoselectivity, good functional group tolerance preservation carbonyl ketone substrates, which offers possibility further transformation products.

Язык: Английский

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Switchable Skeletal Rearrangement of Hexahydro-4H-indol-4-ones: Divergent Synthesis of Dihydroxy-4H-cyclopenta[b]pyridin-4-ones and 8-Alkenyl Oxepane-2,6-diones

Organic Letters, Год журнала: 2024, Номер 26(20), С. 4205 - 4211

Опубликована: Май 14, 2024

An unprecedented base-controlled selective skeletal rearrangement reaction of hexahydro-4

Язык: Английский

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β-Enaminones from cyclohexane-1,3-diones: Versatile precursors for nitrogen and oxygen-containing heterocycles synthesis

Synthetic Communications, Год журнала: 2023, Номер 53(13), С. 953 - 993

Опубликована: Апрель 21, 2023

Abstractβ-Enaminones derived from cyclohexane-1,3-diones reveal a vast variety of bioactivities including anticonvulsant, anti-inflammatory, analgesic, etc. Further, these β-Enaminones are versatile precursors for the synthesis several other important heterocycles that illustrates antimicrobial, antibacterial, antifungal, antitumor, calcium channel antagonist, cardiovascular, antiviral activities, Recently, reactions various β-enaminones with their counterpart example aldehydes, Meldrum's acid, N-arylitaconimides, malononitriles, cyanoacetamide, arylglyoxals, ortho-hydroxybenzyl alcohols, o-hydroxystyrenes, and acenaphthoquinone have been recognized different nitrogen oxygen involving 2-quinolone, 1,4-dihydropyridine, acridine-1,8-dione, indoles, xanthenes, chromenones, These significances enthused us to assemble all newly developed methods creation oxygen-containing heterocycles, which chief attraction this review article.Keywords: Acridine-1cyclohexane-1dihydropyridine3-dione8-dioneβ-enaminonesxanthenes AcknowledgmentsD. S. would like acknowledge support Principal, Jagdish Chandra DAV College, Dasuya, Dist. Hoshiarpur, Punjab, India-144205. M. K. has special thanks Principal Swami Vivekanand Govt College Ghumarwin, HP, India; especially vice-chancellor Lovely Professional University, Phagwara, providing basic amenities during work. P. D. is grateful Director CSIR-IHBT necessary facilities

Язык: Английский

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Arylazo under Extreme Conditions: [2 + 2] Cycloaddition and Azo Metathesis

The Journal of Physical Chemistry C, Год журнала: 2023, Номер 127(18), С. 8482 - 8492

Опубликована: Апрель 26, 2023

The four-membered nitrogen ring (N4-ring) is predicted to be a high-energy density moiety and has been the target of chemical synthesis for quite long time. Here, by compressing 1:1 co-crystal trans-azobenzene trans-perfluoroazobenzene up ∼40 GPa, azo groups were restrained closely in parallel crystal underwent two competitive addition reactions. One [4 + 2] cycloaddition with group as part diene phenyl dienophile. other [2 between groups, which produced an unprecedented N4-ring structure evidenced metathesis product. content significantly increases under higher pressure, we found that it was external pressure decreased kinetic barrier realized such high-tensile moiety. Our work shows high alternative synthetic strategy these structures, can very effective cooperation engineering.

Язык: Английский

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Nickel‐Catalyzed Tandem Ring Contraction of TEMPO and C−N Bond Transamination of Enaminones toward Amino Diversity of Enaminones

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(26)

Опубликована: Июнь 22, 2022

Abstract The reactions of N,N ‐substituted enaminones with TEMPO leading to the synthesis 2,2‐dimethyl pyrrolidine functionalized new have been established by Ni(II) catalysis. interesting ring contraction on as well enaminone C−N bond amination bring tool for generating molecular diversity in amino group fragment.

Язык: Английский

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