Synthesis of pyrazolines via 1,3-dipolar cycloaddition reactions DOI
Himanshu Singh, Rajnish Kumar, Avijit Mazumder

et al.

Synthetic Communications, Journal Year: 2023, Volume and Issue: 53(11), P. 755 - 770

Published: April 19, 2023

Among the large number of reports published on strategies applicable to synthesis pyrazolines and its analogs, The 1,3-dipolar cycloaddition offers a remarkably wide range utility. Many reactions used for provide better selectivity, eco-friendly, less expensive chemical processes. In presented study, we have reviewed various recently adopted pyrazoline which followed mechanism classified them based starting materials.

Language: Английский

Transition-metal-free oxindole synthesis: quinone–K2CO3 catalyzed intramolecular radical cyclization DOI
Shiyuan Wu,

Qiuting Zhao,

Chao Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(10), P. 2593 - 2599

Published: Jan. 1, 2022

A highly efficient transition-metal-free radical cyclization route for the synthesis of oxindoles was developed, using readily available 9,10-phenanthrenequinone (PQ) catalyst together with K 2 CO 3 .

Language: Английский

Citations

12
Asymmetric α-Regioselective [3 + 2] Annulation of Morita–Baylis–Hillman Carbonates: Construction of Three Contiguous Stereocenters with Vicinal Quaternary Carbon Centers DOI
Xiaochen Tian, Yongxing Zhang, Hao Dong

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(15), P. 9593 - 9606

Published: July 14, 2022

Asymmetric α-regioselective annulation of MBH carbonates with 4-arylmethylisoxazol-5-ones has been developed to afford spirocyclic oxindole derivatives containing three contiguous stereogenic centers and vicinal all-carbon quaternary chiral centers. This reaction exhibits a broad substrate scope excellent functional group tolerance. Excellent yields high diastereo- enantioselectivities were obtained in this efficient organocatalytic reaction.

Language: Английский

Citations

11
Organocatalysis in 1,3-Dipolar Cycloaddition Reactions (A Review) DOI

Yulia A. Pronina,

L. A. Teglyai,

A. I. Ponyaev

et al.

Russian Journal of General Chemistry, Journal Year: 2024, Volume and Issue: 94(1), P. 1 - 44

Published: Jan. 1, 2024

Language: Английский

Citations

2
1,3‐Dipolar Cycloaddition of 3‐Chromonyl‐Substituted Glycine Imino Esters with Arylidenes and in situ Diastereodivergent via Retrocycloaddition DOI

Mohammed F. Radwan,

Elghareeb E. Elboray, Hemat M. Dardeer

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(10)

Published: April 3, 2023

1,3-Dipolar cycloaddition through in situ generation of azomethine ylide provides a straightforward and critically important sustainable approach for access to diverse pyrrolidine chemical space. Herein, we developed metal-free AcOH-activated 1,3-dipolar protocol that permits the synthesis uncommon cycloadducts with excellent diastereoselectivity. The challenging substrates 3-formylchromone, glycine ester.HCl arylidene dipolarophile were reacted presence AcONa, which played dual role as base AcOH source, deliver firstly endo-cycloadduct. Under prolonged reaction time at room temperature or heating; endo-adduct underwent diastereodivergent via sequence retro-cycloaddition, stereomutation generated syn-dipole into anti-dipole recycloaddition; furnish scarcely known exo'-cycloadduct high diastereodivergency. worked well broad range stereochemistry obtained was determined without ambiguity using NMR- X-ray analysis. Experimental theoretical DFT calculation studies performed support proposed mechanism elucidate key process seems more beneficial than other transition metal-catalyzed processes.

Language: Английский

Citations

6
An expedient synthesis of C3-arylidene-oxindole derivatives using calcite nanoflowers as an efficient heterogeneous catalyst DOI
Dnyaneshwar Sanap,

Lata Avhad,

Suresh Ghotekar

et al.

Inorganic Chemistry Communications, Journal Year: 2023, Volume and Issue: 149, P. 110387 - 110387

Published: Jan. 2, 2023

Language: Английский

Citations

5
Stereoselective Synthesis of Highly Functionalized Aminobenzothiazole-Fused Spirooxindole Derivatives: in silico and in vitro Anti-Diabetic Studies DOI
Sivan Velmathi,

Narayanasamy Nivetha,

Shashank M. Patil

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(24), P. 4145 - 4162

Published: Aug. 28, 2023

Abstract A series of highly functionalized spirooxindole pyrro­lizidine/pyrrolothiazole derivatives have been synthesized by the three-component 1,3-dipolar cycloaddition reaction benzothiazolyl amides with isatin-based azomethine ylides. The pharmacologically significant bearing one quaternary carbon and four stereocenters were obtained in excellent yields (up to 93%). compounds screened for their anti-diabetic activity against two enzymes, α-glucosidase α-amylase. results exhibited potent inhibitory these especially N-(benzo[d]thiazol-2-yl)-5-fluoro-2-oxo-7′-phenyl-1′,6′,7′,7a′-tetrahydro-3′H-spiro[indoline-3,5′-pyrrolo[1,2-c]thiazole]-6′-carboxamide (6b), which showed compared standard acarbose. Molecular docking receptors interactions a similar way Further, pyrrolothiazole (6b) evinced strong binding compound receptors. Additionally, molecular dynamics simulations carried out confirmed stability active pockets enzymes over 100 ns.

Language: Английский

Citations

5
Enantioselective organocatalytic formal [3+2]-cycloaddition of isatin-derived ketimines with benzylidenemalononitriles and benzylidineindanones DOI

Conor Duffy,

William E. Roe,

Aislinn M. Harkin

et al.

New Journal of Chemistry, Journal Year: 2021, Volume and Issue: 45(47), P. 22034 - 22038

Published: Jan. 1, 2021

Electron-deficient alkenes undergo organocatalysed formal [3+2]-cycloaddition with isatin-derived imines, generating complex spirocyclic products high yield and stereoselectivity.

Language: Английский

Citations

11
Pseudo-multicomponent 1,3-dipolar cycloaddition involving metal-free generation of unactivated azomethine ylides DOI

Asmaa Belabbes,

María de Gracia Retamosa, Francisco Foubelo

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(9), P. 1927 - 1936

Published: Jan. 1, 2023

Thermal C–H activation of imines as a useful tool for the synthesis potential bioactive drugs.

Language: Английский

Citations

4
Copper-Catalyzed Chemoselective O-Arylation of Oxindoles: Access to Cyclic Aryl Carboxyimidates DOI

Prasoon Raj Singh,

Manisha Lamba, Avijit Goswami

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 2926 - 2938

Published: Feb. 14, 2024

We have developed a highly efficient base- and additive-free chemoselective CuO-catalyzed strategy for the O-arylation of 2-oxindoles to synthesize 2-phenoxy-3H-indole 2-phenoxy-1H-indole derivatives in presence diaryl iodonium salts. This method offers variety O-arylated oxindoles good excellent yields under relatively milder reaction conditions. Furthermore, this methodology was extended 2-pyridinone isoindoline-1-one as well.

Language: Английский

Citations

1
Metal-Free Switchable Chemo- and Regioselective Alkylation of Oxindoles Using Secondary Alcohols DOI
Manisha Lamba,

Prasoon Raj Singh,

Tanmay

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11244 - 11260

Published: Aug. 6, 2024

In this study, we have disclosed N-alkylation and C-alkylation reactions of 2-oxindoles with secondary alcohols. Interestingly, these chemoselective are tunable by changing the reaction conditions. Utilization protic solvent Brønsted acid catalyst afforded C-alkylation, whereas, aprotic Lewis in good to excellent yields. Regioselectivity is achieved protecting N-center oxindole C5 alkylated product furnished exclusively. This protocol notable because it demonstrates functionalization at C7 position without need for any directing group N-center. Further, a new has been reported C-H oxygenation benzylic one derivative.

Language: Английский

Citations

1