‘On water synthesis’ of oxindoles bearing quaternary carbon center through C–H (sp3) functionalization of methyl azaarenes

Yaragorla, Srinivasarao; Singh, Garima; Dada, Ravikrishna

doi:10.1016/j.tetlet.2015.12.096

Cited by 33 publications

(12 citation statements)

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“…Another approach of all‐carbon‐quaternary center creation was reported through three‐component on water reaction of 2‐methyl azaarene with isatin and malononitrile at 120 °C for 3–6 h (Scheme ) . A total of 23 examples were made with yields ranging from 73–91 %.…”

Section: Alkylationmentioning

confidence: 99%

“…Various azaarenes were treated with different isatins under standard conditions and afforded different adducts with good yields. Interestingly, when 2‐methyl quinoxaline was used, the desired products 41b were isolated by simple filtration without any column chromatography . 41c was obtained when 2‐methyl pyridine and 2,6‐dimethyl pyridine was treated with isatin and malononitrile with yields 78 % (5 h) and 80 % (5.5 h).…”

Section: Alkylationmentioning

confidence: 99%

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C(sp³)‐H Functionalization of 2‐Methyl Azaarenes: Highly Facile Approach to Aza‐Heterocyclic Compounds

Latha

Yaragorla

2020

Eur J Org Chem

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Quinolines and their derivatives have always been promising leads for drug discovery, material applications and designing new catalysts. In the past decade, C(sp 3 )-H functionalization of 2-methyl azaarenes, particularly 2-methyl quinol- [a] ACYLATIONAlmost the early report of C(sp 3 )-H functionalization of 2methyl quinoline was performed by treating with esters using sodamide or potassium amide as the base. This reaction followed the nucleophilic substitution at the sp 2 center of the ester by the benzylic carbanion which was formed by the base treatment (Scheme 2). A total of 15 compounds were made using this method with the yields ranging from 14-62 %. [11] After a couple of years, another report [12] appeared for this transformation, where 2-methyl quinoline and esters were reacted in the presence of phenyllithium to give corresponding acylated quinolines in 36-80 % yields. Later in 1974, J. F. Wolfe reported another approach by treating 2-methyl quinoline with esters refluxed in dimethoxyethane (DME) using sodium hydride for 1-48 h to obtain the corresponding acylated quinolines in 44-98 % yields. [13] Scheme 2. Minireview

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Section: Alkylationmentioning

confidence: 99%

Section: Alkylationmentioning

confidence: 99%

C(sp³)‐H Functionalization of 2‐Methyl Azaarenes: Highly Facile Approach to Aza‐Heterocyclic Compounds

Latha

Yaragorla

2020

Eur J Org Chem

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“…A one pot three component synthesis of oxindole derivatives by sp3 C–H functionalization of methyl azaarenes with malononitrile and isatins was developed, employing a catalyst‐free on water approach. ( Scheme ) . Two mechanistic pathways were proposed for the reaction.…”

Section: Michael Additions On Watermentioning

confidence: 99%

Recent Advances and Prospects of Organic Reactions “On Water”

et al. 2019

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Organic reactions “On water” is a rapidly developing area over the past few years. Many important classes of reactions like cross‐coupling reactions, pericyclic reactions, C−H activations etc. were performed on water and have shown tremendous increase in the reaction rates due to the potential hydrogen bonding capacity of water. This review focuses on the recent trends and developments in the field of on water reactions applied to organic synthesis and covers literature from 2016–2019.

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“…Therefore, integrating these two structural motifs becomes an interesting topic to synthetic and medicinal chemists, anticipating the better activity . Several synthetic efforts have been accomplished for the nucleophilic addition of 2‐methyl quinolines to α‐keto compounds as shown in Scheme .…”

Section: Introductionmentioning

confidence: 99%

Alkylation of α‐Oxo‐Compounds through C(sp³)‐H Functionalization of 2‐Methyl Quinolines Under Catalyst‐ and Solvent‐Free Conditions

et al. 2020

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Highly facile approach of chemoselective alkylation of α‐oxo compounds such as α‐keto amides, α‐keto esters, isatins, and cyclic‐α‐diketones is developed through C(sp3)‐H functionalization of 2‐methyl quinolines under solvent and catalyst‐free conditions. Further, we complemented the efficacy of this green synthetic protocol by demonstrating the broad substrate diversity, gram‐scale synthesis, and new synthetic transformations of the obtained products.

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‘On water synthesis’ of oxindoles bearing quaternary carbon center through C–H (sp3) functionalization of methyl azaarenes

Cited by 33 publications

References 34 publications

C(sp³)‐H Functionalization of 2‐Methyl Azaarenes: Highly Facile Approach to Aza‐Heterocyclic Compounds

C(sp³)‐H Functionalization of 2‐Methyl Azaarenes: Highly Facile Approach to Aza‐Heterocyclic Compounds

Recent Advances and Prospects of Organic Reactions “On Water”

Alkylation of α‐Oxo‐Compounds through C(sp³)‐H Functionalization of 2‐Methyl Quinolines Under Catalyst‐ and Solvent‐Free Conditions

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‘On water synthesis’ of oxindoles bearing quaternary carbon center through C–H (sp3) functionalization of methyl azaarenes

Cited by 33 publications

References 34 publications

C(sp3)‐H Functionalization of 2‐Methyl Azaarenes: Highly Facile Approach to Aza‐Heterocyclic Compounds

C(sp3)‐H Functionalization of 2‐Methyl Azaarenes: Highly Facile Approach to Aza‐Heterocyclic Compounds

Recent Advances and Prospects of Organic Reactions “On Water”

Alkylation of α‐Oxo‐Compounds through C(sp3)‐H Functionalization of 2‐Methyl Quinolines Under Catalyst‐ and Solvent‐Free Conditions

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Product

Resources

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C(sp³)‐H Functionalization of 2‐Methyl Azaarenes: Highly Facile Approach to Aza‐Heterocyclic Compounds

C(sp³)‐H Functionalization of 2‐Methyl Azaarenes: Highly Facile Approach to Aza‐Heterocyclic Compounds

Alkylation of α‐Oxo‐Compounds through C(sp³)‐H Functionalization of 2‐Methyl Quinolines Under Catalyst‐ and Solvent‐Free Conditions