Facile Chemoselective Reduction of 3-Phenacylideneoxindoles and 2-Oxoacenaphthen-1-ylidene Ketones using the Hantzsch Ester

Gandikota, N. Murthy; Bolla, R. Sekhar; Bandyopadhyay, A.; Viswanath, I. V. Kasi

doi:10.1134/s1070428019080190

Cited by 3 publications

(4 citation statements)

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“…In this regard, efforts have been made to reduce the electron deficient or activated carbon‐ carbon double bond selectively by few research groups. In 2019, Kasi Viswanath and co‐workers described a chemoselective reduction of 3‐phenacylideneoxindoles by using Hantzsch ester and ZnCl 2 (Scheme 1a) [13] . In the same year, Zhang and co‐workers developed a palladium catalysed hydrogenation for the α,β‐unsaturated compounds using sodium hydride as a Michael donor (Scheme 1b) [14] .…”

Section: Methodsmentioning

confidence: 99%

“…In 2019, Kasi Viswanath and co-workers described a chemoselective reduction of 3-phenacylideneoxindoles by using Hantzsch ester and ZnCl 2 (Scheme 1a). [13] In the same year, Zhang and co-workers developed a palladium catalysed hydrogenation for the α,βunsaturated compounds using sodium hydride as a Michael donor (Scheme 1b). [14] In 2013, Zhang and co-workers have disclosed an iridium catalysed asymmetric hydrogenation of αalkylidene succinimides derivatives under very high pressure (H 2 , 20 bar Scheme 1c).…”

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confidence: 99%

“…This result encouraged us to optimize the reaction condition further and, in this regard, we screened the reaction with different organic as well as inorganic bases. We observed that among all the bases, DIPEA proved to be efficient in affording the desired product 2 a (Table 1, Entries 2,[7][8][9][13][14]. Having optimized the photocatalyst and base, we further screened the reaction using different solvents to enhance the yield of desired product 2 a (Table 1, .…”

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confidence: 99%

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Visible Light Promoted Metal‐Free Sustainable Reduction of α‐Alkylidene Oxindoles/Succinimides

2022

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Visible light promoted chemoselective metal free hydrogenation of activated double bond has been achieved via photoredox catalysis. Eosin Y has proved to be an efficient catalyst for the effective reduction of CÀ C double bonds of alkylidene oxindoles and succinimides under visible light. Commercially viable DIPEA has been employed as a sacrificial electron donor and it's in-situ generated cationic radical acts as reductant in this transformation. The method proved to be [a] A.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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Visible Light Promoted Metal‐Free Sustainable Reduction of α‐Alkylidene Oxindoles/Succinimides

2022

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“…In 2019, Kasi Viswanath and co-workers described a chemoselective reduction for the isatin and acenaphthenone derived alkene compounds by using Hantzsch ester and ZnCl2 (Scheme 1a). 12 In the same year, Zhang and co-workers developed a palladium catalysed hydrogenation for the a,b-unsaturated compounds using sodium hydride as a Michael donor (Scheme 1b). 13 In 2013, Zhang and co-workers have disclosed an iridium catalysed asymmetric hydrogenation of a-alkylidene succinimides derivatives under very high pressure (H2, 20 bar Scheme 1c).…”

Section: Scheme 1: Methods For the Hydrogenation Of Different Electron Deficient Alkenesmentioning

confidence: 99%

Visible Light Promoted Metal Free Sustainable Reduction of Activated Carbon-Carbon Double Bonds Without Any External Reductant

Bhowmick

Warghude

Bhat

2021

Preprint

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Visible light promoted chemo-selective metal free hydrogenation of activated double bond has been achieved via photoredox catalysis. Eosin Y has proved to an efficient catalyst for the effective reduction of C-C double bonds of isatins, oxindoles and maleimides under visible light. The method worked efficiently without the aid of any external reductants. Commercially viable DIPEA has been employed as a sacrificial electron donor and it’s in-situ generated cationic radical acts as reductant in this transformation. The method proved to be practical as a broad range of substrates containing activated double bond were easily reduced. The method proved to be scalable on a gram scale and the reduced product has been utilized successfully for the further synthetic application. The systematic and detailed mechanistic studies reveal the reductive quenching of the photocatalyst by the activated double bond.

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Recent developments in the Hantzsch synthesis of dihydropyridines

Vala

Patel

2023

Advances in Heterocyclic Chemistry

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Facile Chemoselective Reduction of 3-Phenacylideneoxindoles and 2-Oxoacenaphthen-1-ylidene Ketones using the Hantzsch Ester

Cited by 3 publications

References 27 publications

Visible Light Promoted Metal‐Free Sustainable Reduction of α‐Alkylidene Oxindoles/Succinimides

Visible Light Promoted Metal‐Free Sustainable Reduction of α‐Alkylidene Oxindoles/Succinimides

Visible Light Promoted Metal Free Sustainable Reduction of Activated Carbon-Carbon Double Bonds Without Any External Reductant

Recent developments in the Hantzsch synthesis of dihydropyridines

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