Ethylbenzene Hydroperoxide: An efficient oxidizing agent for diastereoselective synthesis of Spiroepoxy oxindoles

Valmiki, Praveen K.; Banyangala, Mohan; Varughese, Sunil; Somappa, Sasidhar B.

doi:10.1016/j.tetlet.2022.154126

Cited by 3 publications

(1 citation statement)

References 62 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Particularly, Lewis bases such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-, bicyclic guanidine 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD)-, 1,4-diazabicyclo[2.2.2]octane (DABCO)-, and β-isocupreidine (β-ICD)-catalyzed oxetane ring constructions are well documented for their enantioselectivity and diastereoselectivity. Considering the aforementioned literature reports and our interest in the synthesis of spirocycles and heterocycles, we have developed operationally simple diastereo- and regioselective methods for the construction of spiro-oxetane oxindoles (Scheme D).…”

Section: Introductionmentioning

confidence: 99%

DBU-Catalyzed Diastereo/Regioselective Access to Highly Substituted Spiro-oxetane Oxindoles via Ring Annulation of Isatins and Allenoates

Durugappa,

C S,

Doddamani

et al. 2023

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

A facile and efficient method for the diastereo/regioselective synthesis of highly functionalized spiro-oxetane oxindoles has been described. The 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed reaction proceeds via spiro-annulation of isatins and allenoates. The reaction is compatible with a wide range of isatins containing electron-donating groups (EDGs) and electron-withdrawing groups (EWGs) with various allenoates affording the corresponding products in acceptable yields. It is noteworthy that this is the first protocol for constructing structurally diverse motifs of highly functionalized spiro-oxetane oxindoles of pharmaceutical relevance.

show abstract

Section: Introductionmentioning

confidence: 99%

DBU-Catalyzed Diastereo/Regioselective Access to Highly Substituted Spiro-oxetane Oxindoles via Ring Annulation of Isatins and Allenoates

Durugappa,

C S,

Doddamani

et al. 2023

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

Organic Peroxides

Muianga,

Lasee

2024

Patty's Toxicology

View full text Add to dashboard Cite

Organic peroxides (ROOR′), solid or liquid with the bivalent OO structure. Relatively unstable and highly reactive molecules due to the presence of an oxygen–oxygen linkage. The oxygen–oxygen bond may be cleaved to form highly reactive free radicals and react with many substances (e.g., metals, acids, and bases). ROORs are used in plastics, rubbers, and many industries as initiators, accelerators, promoters, catalysts, activators, and more. Major concerns with ROORs are associated with fires, explosions, and corrosiveness. Reactive oxygen species and free radicals may lead to DNA damage and mutagenesis. Recent work from government agents, academic research laboratories, and manufacturing organizations have focused on physical hazards classification and categorization; and producing best practice protocols for safe handling and storage, control of temperatures, self‐accelerating decomposition temperatures, spills cleaning, disposal, and treatment of ROORs residues. These efforts allow compliance with countries and international regulations. Potential health hazards are associated with eye and skin contact, inhalation, and ingestion. Acute exposure may lead to irritation, allergic response, and potential damage to the eye and skin. As with any irritant or corrosive, dose is a critical consideration with respect to understanding the risk. Chronic exposures, mostly understood in animals but there are human data, can cause a myriad of effects. These may range from respiratory illnesses, to liver, kidney damage, and cancer. The manufacturer's SDS of individual chemical may provide toxicity information. This chapter summarizes chemical‐specific toxicity information on 77 organic peroxide compounds grouped in eight physical hazard categories. NIOSH has fully validated the method for benzoyl peroxide. NTP has released a report on the toxic effects of t ‐butyl perbenzoate and it deserves to be considered. Exposure assessment methods when available were presented. Future research needs to focus on epidemiological and toxicological studies of ROORs.

show abstract

Construction of a highly stable natural silicate-supported molybdenum catalyst for efficient epoxidation of olefins

Yu,

Xiong,

Liang

et al. 2024

Journal of Colloid and Interface Science

View full text Add to dashboard Cite

Ethylbenzene Hydroperoxide: An efficient oxidizing agent for diastereoselective synthesis of Spiroepoxy oxindoles

Cited by 3 publications

References 62 publications

DBU-Catalyzed Diastereo/Regioselective Access to Highly Substituted Spiro-oxetane Oxindoles via Ring Annulation of Isatins and Allenoates

DBU-Catalyzed Diastereo/Regioselective Access to Highly Substituted Spiro-oxetane Oxindoles via Ring Annulation of Isatins and Allenoates

Organic Peroxides

Construction of a highly stable natural silicate-supported molybdenum catalyst for efficient epoxidation of olefins

Contact Info

Product

Resources

About