Spirocyclization and Michael addition of 3-benzylidene succinimides: route to spirocyclopentapyrrolidine-tetraones and benzylidene N-arylpyrrolidine-diones DOI
Pooja Dahiya, Anoop Yadav, Rama Krishna Peddinti

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(46), P. 9192 - 9199

Published: Jan. 1, 2023

Reactions of 3-benzylidene succinimides with 2-substituted 2-hydroxy-indane-1,3-diones and unsaturated pyrazolones are carried out under basic conditions to afford spirocyclized derivatives Michael adducts, respectively, high regio- stereo-selectivities. The most notable aspect the reaction is ability highly reactive benzylidene succinimide act as both an electrophile a nucleophile causing spirocyclization. proceeded mild metal-free products were isolated in good yields. current strategy utilizes simple easily accessible precursors, provides functionally rich medicinal interest two four contiguous stereogenic centres complete regioselectivity excellent diastereoselectivity.

Language: Английский

PTSA‐Catalyzed [3+2] Cycloaddition of in Situ Generated 3‐Ylidene Oxindoles with Coumarin‐Based N‐Phenyl Enamine Derivatives DOI
Anoop Yadav, Pooja Dahiya,

Megha Rawat

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(10)

Published: Jan. 31, 2024

Abstract Brønsted acid mediated [3+2] cycloaddition of coumarin‐based enamines with 3‐ylidene oxindoles generated in situ from 3‐hydroxy‐3‐aroylmethyl enabled the synthesis polyheterocyclic compounds a pyrrolocoumarin core structure highly regioselective manner. The synthetic procedure is efficient and metal‐free, no chromatographic purification products required. chromenopyrrole derivatives bearing an oxindole moiety formed as rapidly interconverting rotamers.

Language: Английский

Citations

1
Metal and acid-free synthesis of acenaphthenone-2-ylidene ketones in PEG 400 and their radical nitration by TBN in water. DOI

Tiyasa Dhar,

Debasish Bera,

Tandrima Chaudhuri

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Metal and acid-free synthesis of acenaphthenone-2-ylidene ketones in PEG 400 has been developed. Using TBN, a radical nitration accomplished for the first time.

Language: Английский

Citations

1
Construction of Polyheterocyclic Compounds by Lewis Acid Mediated Intramolecular [3+2] Cycloaddition Reaction DOI Open Access
Pooja Dahiya, Anoop Yadav,

Rajnish Budhwan

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(31)

Published: July 18, 2023

Abstract An efficient domino approach has been developed for the synthesis of polyheterocyclic derivatives constituting pyrrole moiety. Lewis acid catalyzed reaction 2‐substituted‐2‐hydroxy‐indane‐1,3‐diones and 1,4‐benzoxazinone resulted in formation compounds under metal‐free mild conditions good to excellent yield. The is highly regioselective C−C C−N bond construction proceeded via intramolecular [3+2] cycloaddition reaction. protocol efficient, obviates column chromatography products are obtained by simple filtration followed washing with solvent.

Language: Английский

Citations

3
Spirocyclization and Michael addition of 3-benzylidene succinimides: route to spirocyclopentapyrrolidine-tetraones and benzylidene N-arylpyrrolidine-diones DOI
Pooja Dahiya, Anoop Yadav, Rama Krishna Peddinti

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(46), P. 9192 - 9199

Published: Jan. 1, 2023

Reactions of 3-benzylidene succinimides with 2-substituted 2-hydroxy-indane-1,3-diones and unsaturated pyrazolones are carried out under basic conditions to afford spirocyclized derivatives Michael adducts, respectively, high regio- stereo-selectivities. The most notable aspect the reaction is ability highly reactive benzylidene succinimide act as both an electrophile a nucleophile causing spirocyclization. proceeded mild metal-free products were isolated in good yields. current strategy utilizes simple easily accessible precursors, provides functionally rich medicinal interest two four contiguous stereogenic centres complete regioselectivity excellent diastereoselectivity.

Language: Английский

Citations

2