Enantioselective synthesis of 3-hydroxy- and 3-amino-3-alkynyl-2-oxindoles by the dimethylzinc-mediated addition of terminal alkynes to isatins and isatin-derived ketimines

Prieto, Elena; Martin, John D.; Nieto, Javier; Andrés, Celia

doi:10.1039/d3ob01023f

Cited by 3 publications

References 80 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Incredible Indolinedione Derivatives Nucleus in the Development of Anti‐Diabetic Drugs: Exploring the Mechanistic Studies, Design, and Structure‐Activity Relationship

Khanna,

Jyoti,

Kumar

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

Diabetes mellitus, a prevalent metabolic disorder, necessitates continuous exploration for innovative therapeutic agents. Indolinedione has garnered attention for its potential as an antidiabetic scaffold for its structurally diverse nucleus. The search for novel and effective antidiabetic agents has led to the exploration of natural compounds and synthetic derivatives. The review commences with an in‐depth exploration of the biochemical underpinnings of diabetes mellitus, emphasizing rational design strategies employed for modifying the indolinedione nucleus, encompassing various synthetic methodologies aimed at enhancing its pharmacological properties and docking studies. The multifaceted pharmacological properties and diverse synthetic derivatives of indolinedione offer a fertile ground for further exploration in preclinical and clinical studies. As research in this field progresses, indolinedione may emerge as a valuable addition to the arsenal of antidiabetic therapeutics, providing new avenues for the effective management of diabetes mellitus.

show abstract

Incredible Indolinedione Derivatives Nucleus in the Development of Anti‐Diabetic Drugs: Exploring the Mechanistic Studies, Design, and Structure‐Activity Relationship

Khanna,

Jyoti,

Kumar

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

show abstract

Five-membered ring systems: Pyrroles and benzo analogs

Shan,

Lopchuk

2024

Progress in Heterocyclic Chemistry

View full text Add to dashboard Cite

Recent Advances in Asymmetric Addition Reactions to Isatins

Xie,

Li,

Chen

et al. 2024

Synthesis

View full text Add to dashboard Cite

The 3-substituted-3-hydroxy-2-oxindole scaffolds are not only widely encountered in bioactive compounds but also serve as versatile building blocks for the construction of diverse valuable architectures. Although numerous synthetic methodologies have been developed over the past decades, the asymmetric addition of nucleophiles or their equivalents to isatin substrates has proved to be one of the most efficient strategies for the synthesis of chiral 3-substituted-3-hydroxy-2-oxindoles. This Short Review aims to summarize the significant progress achieved in this field in recent years, with particular attention paid to reaction development, mechanism, and stereo-induction models.

show abstract

Enantioselective synthesis of 3-hydroxy- and 3-amino-3-alkynyl-2-oxindoles by the dimethylzinc-mediated addition of terminal alkynes to isatins and isatin-derived ketimines

Abstract: A common protocol for enantioselective alkynylation of isatins and isatin-derived ketimines using terminal alkynes and Me2Zn in the presence of a catalytic amount of a chiral perhydro-1,3-benzoxazine with moderate to...

Cited by 3 publications

References 80 publications

Incredible Indolinedione Derivatives Nucleus in the Development of Anti‐Diabetic Drugs: Exploring the Mechanistic Studies, Design, and Structure‐Activity Relationship

Incredible Indolinedione Derivatives Nucleus in the Development of Anti‐Diabetic Drugs: Exploring the Mechanistic Studies, Design, and Structure‐Activity Relationship

Five-membered ring systems: Pyrroles and benzo analogs

Recent Advances in Asymmetric Addition Reactions to Isatins

Contact Info

Product

Resources

About