Ru(II)-Catalyzed One-Pot Synthesis of 1,2-Hydropyridines via a Three-Component Reaction DOI
Juntao Yang, Bingxian Liu, Junbiao Chang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(9), P. 1476 - 1480

Published: March 1, 2023

A ruthenium(II)-catalyzed one-pot synthesis of highly substituted 1,2-dihydropyridines (DHPs) via a three-component reaction system has been realized. The is conducted using simple Ru(II) catalyst without the addition specific ligands. catalytic exhibits good functionality tolerance with wide range starting materials. DHPs obtained can be easily converted into tetrahydropyridines and azabicyclo[4.2.0]octa-4,7-dienes by subsequent reduction or [2 + 2] cycloaddition reaction.

Language: Английский

Research on catalytic application of Fe3O4@AAPA-AP-CuCl2 nanocomposite: First nanomagnetic copper catalyst for preparation of aryl nitriles from aldehydes DOI
Ali Noory Fajer, Hussein Ali Al‐Bahrani,

Abud Amir Hussan Kadhum

et al.

Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1296, P. 136800 - 136800

Published: Oct. 11, 2023

Language: Английский

Citations

23
“In-Water” Three-Component One-Pot Reaction for the Facile Synthesis of Densely Functionalized 2,3-Dihydro-1H-pyrrol-2-ols and Mechanistic Insight DOI

Saigal Saigal,

Nallakantham Sudheer,

Subash C. Sahoo

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2024, Volume and Issue: 12(35), P. 13336 - 13351

Published: Aug. 22, 2024

An environmentally friendly multicomponent reaction strategy for the synthesis of functionally rich all-carbon substituted 2,3-dihydro-1H-pyrrol-2-ols "in-water" at room temperature has been reported. Water plays an indispensable role in presence readily available catalytic surfactants sodium dioctylsulfosuccinate and dodecyl sulfate to effectuate transformation, as proved by inferior results obtained organic solvents. A wide display substrate scope functional group compatibility permits diversity generation a mild operationally simple fashion. High product yields, fast rate, recoverability/recyclability catalysts, high TON/TOF, ease purification final products filtration, AE values, excellent E-factor count with score low possible highlight "greenness" this approach. Feasibility "gram-scale" synthetic elaboration offer notable advantages. The mechanistic understanding intercepting labile "imine" intermediate realized through sequence imine formation Mannich-type followed intramolecular N-cyclization.

Language: Английский

Citations

2
Asymmetric [5+1] Annulation via C–H Activation/1,4-Rh Migration/Double Bond Shift Using a Transformable Pyridazine Directing Group DOI

Man Zhu,

Yuyao Zhao,

Xingwei Li

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(11), P. 1839 - 1844

Published: March 13, 2023

N-Heterocycle-assisted C-H activation/annulation reactions have provided new concepts for the construction and transformation of azacycles. In this work, we disclose a [5+1] annulation reaction using novel transformable pyridazine directing group (DG). The DG-transformable mode led to heterocyclic ring accompanied by original via activation/1,4-Rh migration/double bond shift pathway, affording skeleton pyridazino[6,1-b]quinazolines with good substrate scope under mild conditions. Diverse fused cyclic compounds can be achieved derivatization product. asymmetric synthesis was also realized afford enantiomeric products stereoselectivity.

Language: Английский

Citations

5
Research on the catalytic activity of MNP-[Dop-OH]-CuBr2 nanocomposites: novel and stable reusable nanocatalysts for the synthesis of 1,3,5-triazine derivatives DOI Creative Commons

Shouchun Feng,

Jinwang Tan,

Yufan Ma

et al.

RSC Advances, Journal Year: 2023, Volume and Issue: 13(24), P. 16078 - 16090

Published: Jan. 1, 2023

In recent years, magnetic nanocatalysts have been recommended as one of the best catalysts by chemists. Among nanoparticles, Fe3O4 nanoparticles are highly suitable due to their properties, chemical stability and low toxicity. These can be separated via separation after process is over reused regeneration. Owing importance 1,3,5-triazine derivatives in pharmaceutical medicinal chemistry, synthesis these compounds always important goals organic this research work, we first successfully synthesized CuBr2 immobilized on functionalized with Dop-OH (prepared reaction MNP-dopamine 2-phenyloxirane) nanocomposites then investigated catalytic application an oxidative coupling amidine hydrochlorides alcohols air. Recycling experiments clearly revealed that MNP-[Dop-OH]-CuBr2 could for at least 8 times without much loss activity.

Language: Английский

Citations

3
Construction of Nitrogen Spirocycles in a Tandem Co(III)‐catalyzed C−H Activation/Dipolar Cycloaddition Reaction DOI
Jakub Brześkiewicz, Rafał Loska

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(23), P. 4241 - 4247

Published: Oct. 30, 2023

Abstract Complex spirocyclic isoindolines and pyrrolidines are formed in a tandem process involving Co(III)‐catalyzed dienylation of cyclic C‐aryl nitrones with 2,3‐butadien‐1‐ol carbonates, followed by intramolecular 1,3‐dipolar cycloaddition. The nitrone moiety serves both as directing group for the C(aryl)−H activation dipole cycloaddition step. High regioselectivity fused vs. bridged product can be obtained adjusting reaction temperature. Reactions substituted allenic substrates provide heterocycles additional stereocenters usually complete diastereoselectivity. products were readily transformed further into other complex nitrogen‐containing systems.

Language: Английский

Citations

3
Dirhodium-Catalyzed Transannulation ofN-Sulfonyl-1,2,3-triazoles to 2,3-Dehydropiperazines DOI
Michael J. Nutt,

Jack W. Annear,

Kieran D. Jones

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(16), P. 11968 - 11979

Published: July 31, 2023

The dirhodium(II)-catalyzed synthesis of a range C2-substituted 2,3-dehydropiperazines using 1-mesyl-1,2,3-triazoles and β-haloalkylcarbamates is reported. reaction proposed to proceed through an α-imino rhodium carbene 1,3-insertion into N-H followed by base-mediated cyclization. C-Substituted dehydropiperazines can also be conducted directly from terminal alkynes in three-step, one-pot operation, forming the triazole situ. This methodology has been expanded afford several 2,5-disubstituted as well larger 4,5,6,7-tetrahydro-1H-1,4-diazepine derivative.

Language: Английский

Citations

2
Recent Breakthroughs in Ring-Opening Annulation Reactions of Aziridines DOI
Deepak Ranjan Mishra, Nilima Priyadarsini Mishra

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 27, 2024

Aziridine is a fascinating core which enables synthesis of diverse N-heterocycles comprising natural product analogs and pharmaceutical candidates.

Language: Английский

Citations

0
Advances in Selected Heterocyclization Methods DOI
Vladimir Gevorgyan, Mónica Rivas

Synlett, Journal Year: 2023, Volume and Issue: 34(13), P. 1554 - 1562

Published: March 10, 2023

Abstract This Account summarizes efforts in our group toward synthesis of heterocycles the past decade. Selected examples transannulative heterocyclizations, intermediate construction reactive compounds en route to these important motifs, and newer developments a radical approach are outlined. 1 Introduction 2 Transannulative Heterocyclization 2.1 Rhodium-Catalyzed 2.2 Copper-Catalyzed 3 Synthesis Heterocycles from Reactive Precursors 3.1 Diazo Compounds 3.2 Alkynones 4 Radical 4.1 Light-Induced 4.2 Light-Free 7 Conclusion

Language: Английский

Citations

1
Synthesis of 2,4‐dihydrochromeno[3,4‐d][1,2,3]triazoles and 5‐(2H‐chromen‐3‐yl)‐1H‐tetrazoles via regioselective 1,3‐dipolar cycloaddition of 2H‐chromene‐3‐carbonitriles with NaN3 DOI
Deepak Ranjan Mishra, Bhabani Shankar Panda, Mohammed Ansar Ahemad

et al.

ChemistrySelect, Journal Year: 2022, Volume and Issue: 7(46)

Published: Dec. 8, 2022

Abstract Conjugated cyano cyclo‐olefins modified as highly regioselective dipolarophiles in 1,3‐dipolar cycloaddition with NaN 3 to synthesize corresponding fused 1,2,3‐triazole and 1 H ‐tetrazole derivatives. The first example of catalytic 2 ‐chromene‐3‐carbonitriles subsequent elimination/cyclization functionality is designated. In presence amount p ‐TSA or AgNO , react discretely producing 2,4‐dihydrochromeno[3,4‐d][1,2,3]triazoles 5‐(2 ‐chromen‐3‐yl)‐1 ‐tetrazoles respectively, good excellent yields (i. e. 51–88 % 85–97 %) high regioselectivity wide substrate scope adequacy.

Language: Английский

Citations

2
Ru(II)-Catalyzed One-Pot Synthesis of 1,2-Hydropyridines via a Three-Component Reaction DOI
Juntao Yang, Bingxian Liu, Junbiao Chang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(9), P. 1476 - 1480

Published: March 1, 2023

A ruthenium(II)-catalyzed one-pot synthesis of highly substituted 1,2-dihydropyridines (DHPs) via a three-component reaction system has been realized. The is conducted using simple Ru(II) catalyst without the addition specific ligands. catalytic exhibits good functionality tolerance with wide range starting materials. DHPs obtained can be easily converted into tetrahydropyridines and azabicyclo[4.2.0]octa-4,7-dienes by subsequent reduction or [2 + 2] cycloaddition reaction.

Language: Английский

Citations

0