Cycloaddition of isatin-derived MBH carbonates and 3-methyleneoxindoles to construct diastereoselective cyclopentenyl bis-spirooxindoles and cyclopropyl spirooxindoles: Catalyst controlled [3 + 2] and [2 + 1] annulations

Warghude, Prakash K.; Dharpure, Pankaj D.; Bhat, Ramakrishna G.

doi:10.1016/j.tetlet.2018.10.004

Cited by 23 publications

(11 citation statements)

References 77 publications

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“…MBH carbonate is a valuable three‐carbon synthon [ 22 ] and has been employed in the construction of multifunctional spirocyclic oxindoles from the corresponding 3‐alkenyl oxindoles as Michael acceptors and dienophiles. [ 23 ] 3‐Alkenyloxindole and MBH carbonate 36 in the presence of DABCO were effectively utilised for the [2+1] annulation to synthesize bis ‐oxindole derivatives 37 appended with spiro‐cyclopropyl skeletons (Scheme 10).…”

Section: Synthesis Of Spirocyclopropyl Oxindolesmentioning

confidence: 99%

Syntheses and Applications of Spirocyclopropyl Oxindoles: A Decade Review

2020

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Spirocyclopropyl oxindole represents an emerging framework by unique amalgamation of versatile 2‐oxindole motif and highly strained cyclopropane unit. This scaffold is remarkable for its diverse medicinal and synthetic applications. The present review delivers a comprehensive overview of the strategies to afford spirocyclopropyl oxindoles and their potential synthetic transformations. The syntheses of spirocyclopropyl oxindoles have been described based on the type of precursors, including isatin, 3‐alkenyl oxindole, diazooxindole, oxindole, and 3‐chlorooxindole. Besides, the utility of different cyclopropanation reagents like sulfur ylide, MBH‐carbonate, carbenoid, vinyl selenone, etc. have also been emphasized. Furthermore, various ring‐expansion/opening reactions of spirocyclopropane oxindoles using dipolarophiles/nucleophiles have critically been illustrated.

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Section: Synthesis Of Spirocyclopropyl Oxindolesmentioning

confidence: 99%

Syntheses and Applications of Spirocyclopropyl Oxindoles: A Decade Review

2020

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“…From this set, the tertiary amines DMAP and DABCO were efficiently used for cycloaddition between Morita–Baylis–Hillman carbonates 261 and 3‐methyleneoxyindoles 271 to obtain two different types of spirooxindoles 269 and 270 under mild conditions, in good yield ( Scheme 71). [267] …”

Section: Using the [3+2] Annulation Reaction Of Morita‐baylis‐hillmanmentioning

confidence: 99%

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Гатауллин

2020

Helvetica Chimica Acta

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The review covers the results of studies published in the literature on the synthesis of spiro-linked heterocycles of the indole, quinoline, benzoxazine, benzothiazine, indenoquinoxaline, pyridopyrimidine, and acridine series. Possible approaches to the synthesis of spirocycles through a sequence of well-known Knoevenagel, Michael reactions, deamination cyclization of 1,2-dicarbonyl, CH-acid compounds, direct cycloaddition of activated olefins to isatins, 3-alkylideneindoles, 2-oxindoles, in situ generated azomethine ylides, indenoquinoxalines are analyzed. Attention is drawn to approaches to the preparation of spiro-fused compounds using reactions of intra-and intermolecular dearomatization of indoles. Recent advances in the synthesis of spiro-linked benzo heterocycles from derivatives of 2-olefin substituted anilines are summarized. The examples of the synthesis of spiro-fused heterocycles by means of metal complexes catalyzed decomposition of diazo compounds are given. Some syntheses of biologically active representatives are shown, as well as the use of transformations of spiroheterocycles in the preparation of other heterocycles.

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“…Recently, the Bhat's group developed another catalyst‐controlled switchable [3+2] and [2+1] annulations of isatin‐derived MBH carbonates 2 and 3‐methyleneoxindoles 77 (Scheme ) . Under the catalysis of DMAP, bispirooxindoles 90 appended with a cyclopentene were efficiently constructed with excellent yields and diastereoselectivities though an α‐regioselective [3+2] annulation.…”

Section: Annulations Via Allylic Ylidesmentioning

confidence: 99%

Transformations of Modified Morita‐Baylis‐Hillman Adducts from Isatins Catalyzed by Lewis Bases

Chen

et al. 2019

The Chemical Record

103

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The development of synthetic protocols to access architectures with broad structural and functional diversity from readily available starting materials is very attractive in both organic and medicinal chemistry fields. Toward this objective, the multifunctional isatin‐derived Morita‐Baylis‐Hillman (MBH) adducts provide opportunities to construct a variety of complex scaffolds containing a “privileged” oxindole motif through several catalytic pathways. By forming the ammonium or phosphonium salts with Lewis bases, isatin‐derived MBH adducts can undergo allylic substitutions with a range of nucleophiles, usually in a SN2′‐SN2′ pattern. Besides, assisted by Brønsted bases, the corresponding onium salts can be converted into the allylic ylide intermediates, which can undergo various annulation reactions or even 1,3‐difunctionalizations. Moreover, recent cooperative catalysis of Lewis bases and transition metal complexes further puts forward the application of isatin‐derived MBH adducts. This tutorial review covers the significant transformations of isatin‐derived MBH adducts, mostly in an asymmetric version, catalyzed by various Lewis bases over the past decade.

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Cycloaddition of isatin-derived MBH carbonates and 3-methyleneoxindoles to construct diastereoselective cyclopentenyl bis-spirooxindoles and cyclopropyl spirooxindoles: Catalyst controlled [3 + 2] and [2 + 1] annulations

Cited by 23 publications

References 77 publications

Syntheses and Applications of Spirocyclopropyl Oxindoles: A Decade Review

Syntheses and Applications of Spirocyclopropyl Oxindoles: A Decade Review

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Transformations of Modified Morita‐Baylis‐Hillman Adducts from Isatins Catalyzed by Lewis Bases

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Cycloaddition of isatin-derived MBH carbonates and 3-methyleneoxindoles to construct diastereoselective cyclopentenyl bis-spirooxindoles and cyclopropyl spirooxindoles: Catalyst controlled [3 + 2] and [2 + 1] annulations

Cited by 23 publications

References 77 publications

Syntheses and Applications of Spirocyclopropyl Oxindoles: A Decade Review

Syntheses and Applications of Spirocyclopropyl Oxindoles: A Decade Review

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Transformations of Modified Morita‐Baylis‐Hillman Adducts from Isatins Catalyzed by Lewis Bases

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Product

Resources

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Cycloaddition of isatin-derived MBH carbonates and 3-methyleneoxindoles to construct diastereoselective cyclopentenyl bis-spirooxindoles and cyclopropyl spirooxindoles: Catalyst controlled [3 + 2] and [2 + 1] annulations