Microwave-Mediated, Catalyst-Free Synthesis of 1,2,4-Triazolo[1,5-a]pyridines from Enaminonitriles

Molecules, Год журнала: 2024, Номер 29(4), С. 894 - 894

Опубликована: Фев. 18, 2024

A catalyst-free, additive-free, and eco-friendly method for synthesizing 1,2,4-triazolo[1,5-a]pyridines under microwave conditions has been established. This tandem reaction involves the use of enaminonitriles benzohydrazides, a transamidation mechanism followed by nucleophilic addition with nitrile, subsequent condensation to yield target compound in short time. The methodology demonstrates broad substrate scope good functional group tolerance, resulting formation products good-to-excellent yields. Furthermore, scale-up late-stage functionalization triazolo pyridine further demonstrate its synthetic utility. plausible pathway, based on our findings, proposed.

Язык: Английский

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Access to 8-Aminoindolizine Fused with Quinone via Cu(OAc)2-Catalyzed Domino [4+2] Annulation

Synthesis, Год журнала: 2024, Номер 56(11), С. 1799 - 1806

Опубликована: Фев. 1, 2024

Abstract Cu(OAc)2-catalyzed [4+2] annulation of N-substituted pyrrole-2-carbonitriles with quinones allowed access to a wide range 8-aminoindolizines fused through domino process involving sequence intermolecular Michael addition, Thorpe–Ziegler type cyclization, and aromatization. Biological evaluation the resulting quinone-8-aminoindolizine hybrids revealed significant anticancer effects these compounds in human hepatocellular cells (HepG2) prostate adenocarcinoma (PC-3).

Язык: Английский

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Catalyst-free assembly of a polyfunctionalized 1,2,4-triazole-fused N-heterocycle, 6-acylated pyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 22(2), С. 320 - 336

Опубликована: Ноя. 29, 2023

Highly efficient access to a 1,2,4-triazole-fused pyrrolo[1,2- ]pyrazine skeleton with various substituents at the C2 and C6 sites was achieved from N -substituted pyrrole-2-carbonitrile under catalyst-free conditions leading consecutive formation of pyrazine 1,2,4-triazole rings.

Язык: Английский

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Ligand-Promoted Palladium-Catalyzed β-C(sp3)–H Arylation of Ketones Using Acetohydrazide as a Transient Directing Group

Synlett, Год журнала: 2024, Номер unknown

Опубликована: Апрель 20, 2024

Abstract A palladium-catalyzed β-C(sp3)–H arylation of aliphatic ketones by using acetohydrazide as a transient directing group has been developed. The reaction proceeds through less-favored [5,5]-bicyclic palladacycle intermediate and is promoted pyridine ligand.

Язык: Английский

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Ir-Catalyzed Asymmetric Hydrogenation of N-Fused Heteroarenes with High Nitrogen Density: An Access to Chiral 2,5-Disubstituted 5,6-Dihydropyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazines

Organic Letters, Год журнала: 2024, Номер 26(35), С. 7363 - 7369

Опубликована: Авг. 23, 2024

A highly enantioselective Ir-catalyzed asymmetric hydrogenation of 2,5-disubstituted pyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazines containing four nitrogen atoms has been first realized. Under additive-free conditions, a variety chiral 5,6-dihydropyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazines can be afforded in high yields (86–98%) with excellent enantioselectivities up to 99% ee. This method provides straightforward strategy for the efficient synthesis multinitrogen polyheterocyclic compounds.

Язык: Английский

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Five-membered ring systems: With more than 1 N atom

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 211 - 257

Опубликована: Янв. 1, 2024

Язык: Английский

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Catalyst-Free Construction of Imidazole-Pyrrolo[1,2-a]pyrazine Hybrid, 2,6-Disubstituted Imidazo[1,2-a]pyrrolo[2,1-c]pyrazine via Regioselective Annulative Functionalizations

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 26, 2024

Highly efficient catalyst-free annulative functionalization approaches to a novel imidazole-pyrrolo[1,2-

Язык: Английский

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