Expeditious entry into carbocyclic and heterocyclic spirooxindoles

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(29), P. 5651 - 5693

Published: Jan. 1, 2022

Recent advances in the chemistry of base-, metal-, nano-metal and organo-catalyst mediated achiral chiral versions structurally diverse pharmaceutically relevant spirooxindoles are gently reviewed.

Language: Английский

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Regiodivergent Organocatalytic Reactions

Catalysts, Journal Year: 2021, Volume and Issue: 11(8), P. 1013 - 1013

Published: Aug. 22, 2021

Organocatalysts are abundantly used for various transformations, particularly to obtain highly enantio- and diastereomeric pure products by controlling the stereochemistry. These applications of organocatalysts have been topic several reviews. emerged as one very essential areas research due their mild reaction conditions, cost-effective nature, non-toxicity, environmentally benign approach that obviates need transition metal catalysts other toxic reagents. Various types including amine catalysts, Brønsted acids, Lewis bases such N-heterocyclic carbene (NHC) cinchona alkaloids, 4-dimethylaminopyridine (DMAP), hydrogen bond-donating gained renewed interest because regioselectivity. In this review, we present recent advances in regiodivergent reactions governed organocatalysts. Additionally, briefly discuss pathways achieving changes conditions solvents, additives, or temperature.

Language: Английский

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Catalytic asymmetric aromatizing inverse electron-demand [4+2] cycloaddition of 1-thioaurones and 1-azaaurones

Chemical Communications, Journal Year: 2021, Volume and Issue: 58(4), P. 553 - 556

Published: Dec. 8, 2021

Using 1-thioaurones and 1-azaaurones as electron-deficient oxa-dienes, an organocatalytic asymmetric aromatizing inverse electron-demand [4+2] cycloaddition with γ-deconjugated butenolides azlactones was developed. A wide range of optically active benzothiophene-fused δ-lactones indole-fused were obtained desirable outcomes (up to 94% yield, >99 : 1 dr 99% ee).

Language: Английский

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Synthesis of novel benzothieno-[3,2’-f][1,3] oxazepines and their isomeric 2-oxo-2H-spiro[benzothiophene-3,3’-pyrrolines] via 1,4-dipolar cycloaddition reaction and their evaluation as cytotoxic anticancer leads

Medicinal Chemistry Research, Journal Year: 2024, Volume and Issue: 33(6), P. 918 - 929

Published: May 11, 2024

Language: Английский

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Advances of α-activated cyclic isothiocyanate for the enantioselective construction of spirocycles

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(21), P. 4610 - 4621

Published: Jan. 1, 2021

α-Activated cyclic isothiocyanates featuring pharmacophores were efficient percusors for the enantioselective construction of intriguing spirocycles.

Language: Английский

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Synthesis of functionalized 3,2′-pyrrolidinyl spirooxindoles via domino 1,6-addition/annulation reactions of para-quinone methides and 3-chlorooxindoles

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 9(3), P. 615 - 626

Published: Dec. 20, 2021

A highly efficient diastereoselective [4 + 1] cycloaddition of ortho -tosylaminophenyl-substituted p -QMs with 3-chlorooxindoles has been developed to afford 3,2′-pyrrolidinyl spirooxindoles.

Language: Английский

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Asymmetric Formal [3+2] Cycloaddition Reactions of 3-Isothio­cyanato Oxindoles: an Update

Synlett, Journal Year: 2022, Volume and Issue: 34(04), P. 301 - 313

Published: Nov. 24, 2022

Abstract 3-Isothiocyanato oxindoles are a class of important building blocks which have been widely used in the synthesis structurally diverse enantioenriched spirooxindoles. In this short review, it is attempted to cover recent synthetic aspects 3-isothiocyanato participated cascade cyclizations last few years (i.e., from 2017 2022), with an emphasis on formal [3+2] cycloaddition reactions. 1 Introduction 2 Organocatalyzed Formal Cycloaddition Oxindoles 3 Lewis Acid Catalyzed 4 Conclusions

Language: Английский

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A squaramide-catalysed asymmetric cascade Michael addition/acyl transfer reaction between unsaturated benzothiophenones and α-nitroketones

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 20(4), P. 840 - 846

Published: Dec. 29, 2021

An efficient and practical organocatalytic asymmetric strategy was developed using unsaturated benzothiophenones α-nitroketones catalysed by bifunctional squaramide via Michael addition acyl transfer steps. A broad range of chiral acyloxybenzothiophene derivatives were obtained in good yields (up to 97%) with excellent enantioselectivities 98% ee). What's more, employing different catalysts can deliver the acyloxy unit at 2-position or 3-position benzothiophene.

Language: Английский

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Diastereoselective Construction of CF₃‐Containing Bispiro[isoquinolone‐pyrrolidine‐benzothiophenone]s through 1,3‐Dipolar Cycloaddition

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(26)

Published: June 6, 2022

Abstract A new protocol to access CF 3 ‐containing bispiro[isoquinolone‐pyrrolidine‐benzothiophenone]s was described. series of 1,3‐dipoles were synthesized from isoquinolinetrione and CH 2 NH . In the presence 10 mol% DABCO, 1,3‐dipolar cycloaddition isoquinolinedione trifluoroethyl ketimines unsaturated benzothiophenones delivered corresponding adducts in excellent yields (up 98 %) diastereoselectivities >20 : 1 dr).

Language: Английский

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Acid‐Controlled Regional Diverse Synthesis of CF₃‐Containing Ketoimines and Application in the Construction of Bispiro[oxindole‐pyrrolidine‐benzothiophenone]s

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

Published: July 11, 2023

Abstract Here described an acid‐controlled regional diverse synthesized process of CF 3 ‐containing ketoimines by the condensation benzo[ b ]thiophene‐2,3‐dione and 2,2,2‐trifluoroethlamine. The imines obtained at either 2‐position or 3‐position can be further used as substrates in asymmetric organocatalyzed [3+2]‐cycloaddition reactions, leading to a library regiodiverse bispiro‐compounds with 85–96 % yield 65–99 ee .

Language: Английский

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