Stereoselective Synthesis of Alkylidene Phthalides

Dragan, Andrei; Jones, D. Heulyn; Kennedy, Alan R.; Tomkinson, Nicholas C. O.

doi:10.1021/acs.orglett.6b01203

Cited by 11 publications

(7 citation statements)

References 51 publications

(22 reference statements)

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“…A similar approach has been reported by Tomkinson et al in 2016 (Scheme 39). [46] The reaction of lithium enolate with N,Ophthaloylhydroxylamine led to the formation of alkylidene phthalides.…”

Section: Reaction Of Enol Ethers With Phthaloyl Derivativesmentioning

confidence: 99%

Preparation of 3‐Alkylidenephthalides: Recent Advances

et al. 2022

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3-Alkylidenephthalides represent an important class of natural compounds which are also valuable synthetic precursors for the preparation of phthalides. While recent reviews reported the great interest of the phthalides in the field of medicinal chemistry, few reports are mentioning the recent progress for the synthesis of their unsaturated homologous in the position 3. So, the aim of this report is to present the latest progresses (since 2010 and until 2021) in the synthesis of 3-alkylidenephtalides.www.eurjoc.org

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Section: Reaction Of Enol Ethers With Phthaloyl Derivativesmentioning

confidence: 99%

Preparation of 3‐Alkylidenephthalides: Recent Advances

et al. 2022

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“…Despite their significant biological activities, there are very few methods known for the stereo‐ and regioselective synthesis of alkylidenephthalides which include Wittig‐Horner reaction of 3‐phosphonylphthalide with carbonyl compounds and phthalic anhydride with phosphoranes, [5] transition metal catalyzed cross‐coupling, [6] carbene [7] as well as Grignard and lithium enolate mediated reactions [8] …”

Section: Figurementioning

confidence: 99%

“…[1] Despite their significant biological activities, there are very few methods known for the stereo-and regioselective synthesis of alkylidenephthalides which include Wittig-Horner reaction of 3-phosphonylphthalide with carbonyl compounds and phthalic anhydride with phosphoranes, [5] transition metal catalyzed cross-coupling, [6] carbene [7] as well as Grignard and lithium enolate mediated reactions. [8] From another perspective, 1,3-indanediones possess significant synthetic and biological applications. [9] The indanedione moiety is an integral part of several natural products and bioactive compounds, for instance, the anti-tumor agent Fredericamycin A.…”

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confidence: 99%

Michael Addition‐Elimination and [4+1] Annulation of Sulfonylphthalide with Hydroxychalcones for the Synthesis of Alkylidenephthalides and Indanediones

et al. 2021

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A protocol for the stereoselective synthesis of alkylidenephthalides and indanediones has been developed through the reaction of o-hydroxychalcones and their styrenyl analogues, respectively, with 3-sulfonylphthalide. The mechanism for the former synthesis involves Michael addition-E 2 elimination sequence, while the latter involves a [4 + 1] Hauser-Kraus annulation. The mechanistic studies reveal that the strategically positioned phenolic group plays a pivotal role in the observed reactivities. The alkylidenephthalides, which are latent 1,4dicarbonyl compounds, were further converted to triarylfurans under Paal-Knorr conditions in good to excellent yields. This protocol unravels several key features such as substrate specific product formation, namely, alkylidenephthalides from chalcones, and indanediones from vinylogous chalcones in their reaction with 3-sulfonylphthalide as well as the role of alkylidenephthalides as 1,4-dicarbonyl surrogates in Paal-Knorr furan synthesis.

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“…in the preparation of benzo-fused nitrogen heterocycles. [287,288] In the interaction of ortho-succinimide substituted benzaldehyde 300 with nitrosobenzene 301 in the presence of cesium carbonate or DBU, dihydrobenzoxazine-pyrrolidone spirocyclic compound 302 is formed. Cesium carbonate was found to be a more efficient catalyst; if an amine base was used as the catalyst, the yield of the reaction product was lower.…”

Section: Synthesis Of Spirocycles Using Partially Hydrogenated Acridimentioning

confidence: 99%

“…In a number of studies, 2,3‐benzoxazine derivatives are also of interest as synthetic equiv. in the preparation of benzo‐fused nitrogen heterocycles [287,288] . In the interaction of ortho ‐succinimide substituted benzaldehyde 300 with nitrosobenzene 301 in the presence of cesium carbonate or DBU, dihydrobenzoxazine‐pyrrolidone spirocyclic compound 302 is formed.…”

Section: Synthesis Of Spirocyclic Quinoxaline Acridine Benzoxazinementioning

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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Stereoselective Synthesis of Alkylidene Phthalides

Cited by 11 publications

References 51 publications

Preparation of 3‐Alkylidenephthalides: Recent Advances

Preparation of 3‐Alkylidenephthalides: Recent Advances

Michael Addition‐Elimination and [4+1] Annulation of Sulfonylphthalide with Hydroxychalcones for the Synthesis of Alkylidenephthalides and Indanediones

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

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