Highly efficient regio and diastereoselective synthesis of functionalized bis-spirooxindoles and their antibacterial properties

Ramesh, P.; Rao, K. Srinivasa; Trivedi, Rajiv; Kumar, B. S. P. Anil; Prakasham, R. S.; Sridhar, Balasubramanian

doi:10.1039/c6ra00613b

Cited by 26 publications

(10 citation statements)

References 46 publications

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“…Along this line, such isatin derivatives have found applications as precursors of aza-dienolates in vinylogous Michael additions to electron-poor olefins or in reaction cascades involving conjugate addition reactions. Apart from one example reported by Trivedi et al 619 in which the benzylimines deriving from isatin produced spirooxindole-pyrrolidines in racemic format (not shown), the remaining examples fall in the field of asymmetric organocatalyzed processes.…”

Section: Vinylogous Amides and Lactamsmentioning

confidence: 99%

New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems

et al. 2020

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The principle of vinylogy states that the electronic effects of a functional group in a molecule are possibly transmitted to a distal position through interposed conjugated multiple bonds. As an emblematic case, the nucleophilic character of a π-extended enolate-type chain system may be relayed from the legitimate α-site to the vinylogous γ, ε, ..., ω remote carbon sites along the chain, provided that suitable HOMO-raising strategies are adopted to transform the unsaturated pronucleophilic precursors into the reactive polyenolate species. On the other hand, when “unnatural” carbonyl ipso -sites are activated as nucleophiles (umpolung), vinylogation extends the nucleophilic character to “unnatural” β, δ, ... remote sites. Merging the principle of vinylogy with activation modalities and concepts such as iminium ion/enamine organocatalysis, NHC-organocatalysis, cooperative organo/metal catalysis, bifunctional organocatalysis, dicyanoalkylidene activation, and organocascade reactions represents an impressive step forward for all vinylogous transformations. This review article celebrates this evolutionary progress, by collecting, comparing, and critically describing the achievements made over the nine year period 2010–2018, in the generation of vinylogous enolate-type donor substrates and their use in chemical synthesis.

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Section: Vinylogous Amides and Lactamsmentioning

confidence: 99%

New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems

et al. 2020

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Section: Synthesis Of Spiroisoxazolidinesmentioning

confidence: 99%

“…In 2016, functionalized bis-spirooxindoles 103 were synthesized from Trivedi and co-workers by diastereoselective 1,3-dipolar cycloadditon of substituted isatins 100, benzylamines 101, and enones 102 in water and ceric ammonium nitrate (CAN) as catalyst at 100 °C (Scheme 21) [69]. The effect of substituents on isatin substrates was evaluated observing that the halogen groups gave spirooxindoles in high yields, while a methoxy group on the benzylamine substrates produced the final products in low yield in contrast to fluoro-functionalized benzylamines.…”

Section: Synthesis Of Spiroisoxazolidinesmentioning

confidence: 99%

Recent Developments on 1,3-Dipolar Cycloaddition Reactions by Catalysis in Green Solvents

et al. 2020

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The use of eco-compatible synthetic procedures in organic reactions and, in particular, in 1,3-dipolar cycloaddition reactions, has recently received a great deal of attention and considerable progress has been achieved in this area in the last years. This review summarizes the approaches currently employed to synthesize heterocyclic compounds by catalyzed 1,3-dipolar cycloadditions in green solvents in the last six years. Our choice to do a selection of the literature from 2014 to 2019 was made considering the absence of a recent review about this period, to our knowledge. Several examples to construct heterocycles by 1,3-dipolar cycloadditions will be discussed in this work subdivided in function of the most important class of non-conventional and green solvents, i.e., ionic liquids (ILs), deep eutectic solvents (DES), and water.

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“…The use of Lewis acids, such as Ceric Ammonium Nitrate (CAN) or TiO 2 , in the formation of spirooxindoles in water has been investigated, giving excellent results (Scheme 18) (Ramesh et al, 2016, 2018). The 1,3-dipolar cycloaddition was performed with 1 mol% of CAN in 2 h, while the reaction was complete after 30 min when heterogeneous TiO 2 nanoparticles were used.…”

Section: 3-dipolar Cycloaddition In Watermentioning

confidence: 99%

Green Protocols in Heterocycle Syntheses via 1,3-Dipolar Cycloadditions

et al. 2019

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The aim of this review is to provide an overview of green protocols for the organic synthesis of heterocycles via 1,3-dipolar cycloaddition. Particular attention has been devoted to the use of green solvents; reactions performed in ionic liquids, fluorinated solvents and water have been included. Also explored are several protocols that make use of catalyst-free reaction conditions, the use of microwave irradiation and activation by light exposure. Improvements over commonly used organic solvents will be underlined in order to highlight environmental protection aspects and enhancements in regio- and stereo-selectivity.

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Highly efficient regio and diastereoselective synthesis of functionalized bis-spirooxindoles and their antibacterial properties

Abstract: A simple, efficient, regioselective and diastereoselective method has been developed for the synthesis of spirooxindole-pyrrolidines using 0.5 mol% of ceric ammonium nitrate in aqueous medium.

Cited by 26 publications

References 46 publications

New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems

New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems

Recent Developments on 1,3-Dipolar Cycloaddition Reactions by Catalysis in Green Solvents

Green Protocols in Heterocycle Syntheses via 1,3-Dipolar Cycloadditions

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