An easy and practical approach to access multifunctional cylcopentadiene- and cyclopentene-spirooxindoles <i>via</i> [3 + 2] annulation

Warghude, Prakash K.; Sabale, Abhijeet S.; Dixit, Ruchi; Vanka, Kumar; Bhat, Ramakrishna G.

doi:10.1039/d1ob00514f

Cited by 14 publications

(3 citation statements)

References 74 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Finally, this intermediate undergoes protonation, leading to the desired compound 50, while also regenerating DMAP to complete the catalytic cycle ( Scheme 18 ). 56 …”

Section: [3 + 2] Cycloaddition Reactions (32ca)mentioning

confidence: 99%

A concise update on the synthetic transformation of aurones via asymmetric cycloaddition, annulation, and Michael/Mannich reactions

John,

George,

Radhakrishnan

2024

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…Finally, this intermediate undergoes protonation, leading to the desired compound 50, while also regenerating DMAP to complete the catalytic cycle ( Scheme 18 ). 56 …”

Section: [3 + 2] Cycloaddition Reactions (32ca)mentioning

confidence: 99%

A concise update on the synthetic transformation of aurones via asymmetric cycloaddition, annulation, and Michael/Mannich reactions

John,

George,

Radhakrishnan

2024

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…(Scheme 8). [18] The authors proposed a plausible reaction mechaism. As shown in Scheme 9, initially, nucleophilic attack of DMAP to the MBH carbonate gave the quaternary ammonium salt 25.…”

Section: Tertiary Amine-catalyzed [3 + 2] Cyclo-additionsmentioning

confidence: 99%

Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles

Li,

Ma,

Meng

et al. 2023

Adv Synth Catal

View full text Add to dashboard Cite

Spirooxindoles are privileged scaffolds in diverse bioactive natural products and pharmaceuticals, significant achievements for the construction of these molecules have thus been made in the past years. Among them, organocatalysis, in particular, nucleophilic Lewis base catalysis, has recently emerged as an efficient and reliable method for the preparation of diverse and valuable functionalized spirooxindoles. According to different kinds of nucleophilic catalysts, we summarize and classify three catalytic strategies; these are tertiary amine‐catalyzed cycloadditions, NHC‐catalyzed cycloadditions, and tertiary phosphine‐catalyzed cycloadditions, respectively. Through these methods, potential bioactive spirooxindole skeletons owning various functional groups can be produced to enrich the small organic molecule library. In this review, we describe a comprehensive and updated advances of nucleophilic Lewis base catalytic cycloaddition reactions for the construction of spirooxindoles. Meanwhile, the related mechanism and the application of these annulation strategies in natural product total synthesis will be highlighted in detail.

show abstract

“…Initially, we chose isatin-derived MBH carbonate 1a with high reactivity and N -(benzoylmethyl)pyridinium bromide 2a as the model substrates to explore the (3 + 1 + 1) carboannulation reaction. Pleasingly, by using DMAP as the base, the generation of the desired spiro-cyclopentadiene oxindole product 3a was observed (49% yield, Table , entry 1) . No (2 + 1) annulation product was observed in the reaction system.…”

mentioning

confidence: 99%

Formal (3 + 1 + 1) Carboannulation of Morita–Baylis–Hillman Carbonates with Pyridinium Ylides: Access to Spiro-Cyclopentadiene Oxindoles

Tang

Jiang

et al. 2021

Org. Lett.

View full text Add to dashboard Cite

An efficient formal (3 + 1 + 1) carboannulation strategy of Morita–Baylis–Hillman (MBH) carbonates with pyridinium ylides was developed for constructing diversely functionalized spiro-cyclopentadiene oxindoles. The reaction initiates with an SN2′ olefination of MBH carbonates with pyridinium ylides. The in situ generated dienes then engage in a challenging (4 + 1) ylide carboannulation, which has been rarely reported before. The reaction features broad substrate scope as well as high chemo- and regioselectivity. (3 + 1 + 1) carboannulation products could be easily transformed into interesting spiro-cyclopenta[c]furan oxindoles.

show abstract

An easy and practical approach to access multifunctional cylcopentadiene- and cyclopentene-spirooxindoles via [3 + 2] annulation

Abstract: A highly regioselective [3+2] annulation of Morita-Baylis-Hillman (MBH) carbonates of isatin with aurone/thioaurone is developed. Spiroheterocycles such as spirooxindole cyclopentadiene and spirooxindole fused hydroxy cyclopentene derivatives are constructed in one...

Cited by 14 publications

References 74 publications

A concise update on the synthetic transformation of aurones via asymmetric cycloaddition, annulation, and Michael/Mannich reactions

A concise update on the synthetic transformation of aurones via asymmetric cycloaddition, annulation, and Michael/Mannich reactions

Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles

Formal (3 + 1 + 1) Carboannulation of Morita–Baylis–Hillman Carbonates with Pyridinium Ylides: Access to Spiro-Cyclopentadiene Oxindoles

Contact Info

Product

Resources

About