Oxidative Cleavage of C2–C3 Bond in Isatin Using (Diacetoxyiodo)benzene: A Facile Synthesis of Carbamates of Alkyl Anthranilates

Kalbandhe, Amit H.; Kavale, Ashish C.; Thorat, Prerana B.; Karade, Nandkishor N.

doi:10.1055/s-0035-1560990

Cited by 6 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The ring opening of isatin can proceed through divergent pathways to synthesise derivatives of N ‐heterocycles and various benzamides as well, i. e., through N1−C2 cleavage, C2−C3 cleavage, [18] and insertion of other atoms in between C2−C3 bond. Among them, the C3 carbonyl group is the most reactive moiety in isatin compared to the other C2 carbonyl group and N1 amino group and serves as the main entrance to construct spiro heterocycles [19] .…”

Section: Introductionmentioning

confidence: 99%

Single Step Upgradation of Isatin to Bioactive Fused Heterocycles via Ring Expansion Reactions

Chandramani,

Nair,

Sreekumar

et al. 2023

Eur J Org Chem

View full text Add to dashboard Cite

Isatin, also known as indoline‐2,3‐dione, is a fused, N‐heterocyclic aromatic compound first isolated and purified in 1841. Since then, isatin and its derivatives emerged as a hot research topic for the scientific community. The number of research publications on isatin justifies their popularity. Researchers explored isatins and their derivatives as potential candidates in multidisciplinary research areas, including medicinal chemistry, synthetic organic chemistry, and polymer science. Synthetic chemists’ perspective of tailoring isatin and its family members led to more efficient synthesis strategies in which ring‐opening reactions of isatins were particularly significant due to the product's importance. Our investigation aims to group the different types of cascade ring expansion reactions of isatin to synthesise fused heterocyclic compounds such as derivatives of quinolines, quinazolinones, acridines, acridones, and few spiro heterocyclic compounds, all of which highlight an inevitable role in the field of medicinal chemistry.

show abstract

Section: Introductionmentioning

confidence: 99%

Single Step Upgradation of Isatin to Bioactive Fused Heterocycles via Ring Expansion Reactions

Chandramani,

Nair,

Sreekumar

et al. 2023

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

An Electrochemical Route for Special Oxidative Ring‐Opening of Indoles

Qin

Zhao

Zhang

et al. 2021

Chemistry A European J

View full text Add to dashboard Cite

A novel electrochemical protocol for the oxidative cleavage of indoles has been developed, which offers a simple way to access synthetically useful anthranilic acid derivatives. In undivided cells, a wide variety of indoles and alcohol compounds are examined to afford amide ester aromatics without using extra oxidants and stoichiometric metal catalysts, which avoids the formation of undesired byproducts and exhibits high atom economy. The products we described in this perspective represent a synthetic intermediate in numerous drug molecules and industrial chemical reagents and remarkably show potential application in the future.

show abstract

ChemInform Abstract: Oxidative Cleavage of C2—C3 Bond in Isatin Using (Diacetoxyiodo)benzene: A Facile Synthesis of Carbamates of Alkyl Anthranilates.

et al. 2016

View full text Add to dashboard Cite

show abstract

Oxidative Cleavage of C2–C3 Bond in Isatin Using (Diacetoxyiodo)benzene: A Facile Synthesis of Carbamates of Alkyl Anthranilates

Abstract: MS (ESI): m/z (M +) calculated for C 12 H 13 81 Br 2 NO 4 : 394.9211 Found [M + 23]: 418. Methyl 2-(methoxycarbonylamino)-5-nitrobenzoate (2m) 2 :

Cited by 6 publications

References 0 publications

Single Step Upgradation of Isatin to Bioactive Fused Heterocycles via Ring Expansion Reactions

Single Step Upgradation of Isatin to Bioactive Fused Heterocycles via Ring Expansion Reactions

An Electrochemical Route for Special Oxidative Ring‐Opening of Indoles

ChemInform Abstract: Oxidative Cleavage of C2—C3 Bond in Isatin Using (Diacetoxyiodo)benzene: A Facile Synthesis of Carbamates of Alkyl Anthranilates.

Contact Info

Product

Resources

About