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

Expeditious entry into carbocyclic and heterocyclic spirooxindoles DOI

Madhu Ganesh,

Shammy Suraj

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(29), P. 5651 - 5693

Published: Jan. 1, 2022

Recent advances in the chemistry of base-, metal-, nano-metal and organo-catalyst mediated achiral chiral versions structurally diverse pharmaceutically relevant spirooxindoles are gently reviewed.

Language: Английский

Citations

48

Azomethine Ylides—Versatile Synthons for Pyrrolidinyl-Heterocyclic Compounds DOI Creative Commons
Siva S. Panda, Marian N. Aziz, Jacek Stawiński

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(2), P. 668 - 668

Published: Jan. 9, 2023

Azomethine ylides are nitrogen-based three-atom components commonly used in [3+2]-cycloaddition reactions with various unsaturated 2π-electron components. These highly regio- and stereoselective have attracted the attention of organic chemists respect to construction diverse heterocycles potentially bearing four new contiguous stereogenic centers. This review article complies most important azomethine olefinic, (acyclic, alicyclic, heterocyclic, exocyclic ones) reported over past two decades.

Language: Английский

Citations

22

Unraveling the mechanism, regioselectivity, and stereoselectivity of [3 + 2] cycloaddition reactions for anticancer spirooxindole derivatives: A density functional theory study DOI

Khadija Zaki,

Mohamed Ouabane,

Abdelouahid Sbai

et al.

Computational and Theoretical Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 115086 - 115086

Published: Jan. 1, 2025

Language: Английский

Citations

0

Structural insights into 2-oxindole-forming monooxygenase MarE: Divergent architecture and substrate positioning versus tryptophan dioxygenases DOI Creative Commons
Inchul Shin,

Romie C. Nguyen,

Samuel R. Montoya

et al.

Journal of Biological Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 108241 - 108241

Published: Jan. 1, 2025

Language: Английский

Citations

0

Morphological Profiling Identifies the Motor Protein Eg5 as Cellular Target of Spirooxindoles DOI Creative Commons
Jie Liu,

Shubhadip Mallick,

Yusheng Xie

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(21)

Published: March 16, 2023

Oxindoles and iso-oxindoles are natural product-derived scaffolds that provide inspiration for the design synthesis of novel biologically relevant compound classes. Notably, spirocyclic connection oxindoles with has not been explored by nature but promises to structurally related compounds endowed bioactivity. Therefore, methods their efficient conclusive discovery cellular targets highly desirable. We describe a selective RhIII -catalyzed scaffold-divergent spirooxindole-isooxindoles spirooxindole-oxindoles from differently protected diazooxindoles N-pivaloyloxy aryl amides which includes functional group-controlled Lossen rearrangement as key step. Unbiased morphological profiling corresponding collection in Cell Painting assay efficiently identified mitotic kinesin Eg5 target spirooxindoles, defining unique inhibitor chemotype.

Language: Английский

Citations

10

1-Styryl-1,3-diketones in the synthesis of spiro[oxindole-3,2′-pyrrolidines] with notable anticancer activity DOI
Nikolay S. Zimnitskiy, Vladislav Yu. Korotaev,

Maria V. Ulitko

et al.

Molecular Diversity, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 4, 2025

Language: Английский

Citations

0

Synthesis of spiroisoxazoline oxindoles by base-promoted annulation of oxime esters and isatins DOI
Si-Wei Chen,

Xu‐Hua Hu,

Ling Wu

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: 159, P. 155506 - 155506

Published: March 6, 2025

Language: Английский

Citations

0

Graphene oxide decorated N-heterocyclic carbene–nickel complex with pendant caffeine for C–H arylation of benzoxazole DOI

Taha Aalhusaini,

Dattaprasad M. Pore, Gajanan Rashinkar

et al.

Journal of Organometallic Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 123637 - 123637

Published: April 1, 2025

Language: Английский

Citations

0

Substrate‐Controlled Regioselectivity Switch in a Three‐Component 1,3‐Dipolar Cycloaddition Reaction to Access 3,3′‐Pyrrolidinyl‐Spirooxindoles Derivatives DOI
Kai‐Kai Wang, Yan‐Li Li, Rongxiang Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(12), P. 2047 - 2052

Published: May 12, 2022

Abstract The additive‐free 1,3‐dipolar cycloaddition reaction of isatin‐derived azomethine ylides with α‐cyano‐α,β‐unsaturated compounds was developed, which enabled diversity‐oriented synthesis a series novel and structurally complex 3,3′‐pyrrolidinyl‐spirooxindoles derivatives containing four contiguous two quaternary stereogenic centers in high yields (up to 92%) excellent diastereoselectivities >25:1 dr). displays switchable regioselectivity depending on the steric effect substrates. magnified image

Language: Английский

Citations

15

Recent Progress in Heterocycle Synthesis: Cyclization Reaction with Pyridinium and Quinolinium 1,4-Zwitterions DOI Creative Commons
Zhen‐Hua Wang, Yong You, Jian‐Qiang Zhao

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(7), P. 3059 - 3059

Published: March 29, 2023

Heteroarene 1, n-zwitterions are powerful and versatile building blocks in the construction of heterocycles have received increasing attention recent years. In particular, pyridinium quinolinium 1,4-zwitterions been widely studied used a variety cyclization reactions due to their air stability, ease use, high efficiency. Sulfur- nitrogen-based 1,4-zwitterions, types emerging heteroatom-containing synthons, attracted much from chemists. These which contain multiple reaction sites, successfully synthesis three- eight-membered cyclic compounds over last decade. this review, we present exciting progress made field sulfur- 1,4-zwitterions. Moreover, mechanistic insights, transition states, some synthetic applications, challenges opportunities also discussed. We hope provide an overview for chemists who interested heterocycle with

Language: Английский

Citations

7