Palladium‐Catalyzed Selectivity Controlled Highly Efficient Carbonylative Synthesis of Isoquinoline‐1,3(2H,4H)‐diones and Indanones

ChemistryEurope, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 7, 2025

Abstract Compared to the methods that rely on complex and structurally unique substrates for synthesis of heterocyclic compounds through intra‐ intermolecular cyclization, strategies starting from simple readily available substrates, combined with finely tuned catalytic system achieve different chemoselectivity, offer significant advantages in terms efficiency, cost‐effectiveness, versatility. Herein, we present a palladium‐catalyzed carbonylation strategy enables selective efficient isoquinoline‐1,3(2 H ,4 )‐dione indanone derivatives via distinct reaction pathways. Notably, chemoselectivity was not determined by differences reactivity at sites but instead arises generation active palladium species under nearly identical conditions, which subsequently react same site lead products.

Language: Английский

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Indoles in Drug Design and Medicinal Chemistry

European Journal of Medicinal Chemistry Reports, Journal Year: 2025, Volume and Issue: unknown, P. 100252 - 100252

Published: Feb. 1, 2025

Language: Английский

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Asymmetric Reductive Heck Cyclization of 3-(Adamantan-1-yl)-1-(2-bromophenyl)prop-2-en-1-one: Highly Enantioselective Synthesis of 3-(Adamantan-1-yl)indan-1-one

Russian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 61(2), P. 361 - 365

Published: Feb. 1, 2025

Language: Английский

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Enantioselective access to spiro[2,3-dihydrofuran-2,2′-inden-1-ones]viazinc catalyzed [3 + 2] annulation of α-hydroxy-1-indanones with yne–enones

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(16), P. 4061 - 4067

Published: Jan. 1, 2023

An enantioselective construction of spiro[1-indanone-dihydrofurans] has been accomplished through zinc-catalyzed [3 + 2] annulation via a Brønsted base and Lewis acid cooperative activation model.

Language: Английский

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Dihydro-10H-indeno[1,2-b]benzofurans and Tetrahydroindeno[1,2-c]isochromenes via Stereoselective Intramolecular Carbocation Cascade Cyclization

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 2964 - 2983

Published: Feb. 12, 2024

Nazarov cyclization of the (E)-(2-stilbenyl)methanols under catalysis p-TsOH immobilized on silica (PTS-Si) proceeded to give corresponding indanyl cation with exclusive trans relationship at two newly formed adjacent stereogenic centers. The ensuing intramolecular nucleophilic addition by MOM-protected phenol (m = 0) or benzyl alcohol 1) furnished Indane-fused benzofuran [5/5] isochroman [5/6] system, respectively, cis stereocontrol two-carbon ring junction. Thus, in a single step, from nonchiral starting materials, cascade carbocation (CCC) oxygen-containing Indane fused-ring systems moderate good yields excellent stereoselectivity all three contiguous

Language: Английский

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Regio- and diastereoselective synthesis of diverse spirocyclic indenes by cyclization with indene-dienes as two carbon building blocks

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(33), P. 6681 - 6686

Published: Jan. 1, 2023

We report a base-promoted cyclization with indene-dienes as two carbon building blocks toward diverse spirocyclic indene scaffolds including hexacyclic spiroindenes bearing benzo pyran motifs and pentacyclic containing oxindole units in high yields excellent diastereoselectivities.

Language: Английский

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Synthesis of arene-functionalized fused heterocyclic scaffolds via a regioselective cascade 1,4-conjugate addition/5-exo-dig annulation strategy

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(46), P. 9159 - 9172

Published: Jan. 1, 2023

Facile access to furan fused heterocyclic scaffolds through a regioselective cascade reaction of propargylamines with 4-hydroxy-2H-pyran-2-ones and 4-hydroxy-6-methylpyridin-2(1H)-one has been achieved. This presumably involves the formation ortho-alkynyl quinone methide (o-AQM), 1,4-conjugate addition, followed by 5-exo-dig annulation, 1,3-H shift process. Moreover, provides new efficient method for synthesis highly sterically congested 3-phenolic furo[3,2-c]pyran-4-ones furo[3,2-c]pyridin-4(5H)-ones ring from readily available starting materials in good high yields (50-82%) broad functional group compatibility single step. Significantly, strategy described here is easily scalable several useful synthetic transformations prepared arene-functionalized 4H-furo[3,2-c]pyran-4-ones were also performed.

Language: Английский

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Bismuth(III) Triflate: An Economical and Environmentally Friendly Catalyst for the Nazarov Reaction

Published: Jan. 3, 2024

We describe the use of bismuth (III) triflate as an efficient and environmentally friendly catalyst for Nazarov reaction aryl vinyl ketones, leading to synthesis 3-aryl-2-carboethoxy-1-indanones 3-aryl-1-indanones. By changing temperature time, it was possible modulate reactivity, allowing two different products in good excellent yields (3-aryl-2-carboethoxy-1-indanones 3-aryl-2-carbethoxy-1-indanones). The does not need additives is insensitive both air moisture. preliminary biological evaluation some indanones show a promissory profile against human cancer line cells.

Language: Английский

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Stoichiometric Reactions between the Rhodium/Iridium Complexes and 2‐Vinylbenzaldehyde Derivatives: Synthesis and Characterization of Rhodaindanone and Iridaindanone Complexes

European Journal of Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 27(7)

Published: Jan. 13, 2024

Abstract Utilizing rhodium complexes to catalyze 2‐vinylbenzaldehyde derivatives has proven be a valuable strategy in constructing indanone moieties. In this study, the stoichiometric reactions of Wilkinson's catalyst RhCl(PPh 3 ) with were investigated, leading formation rhodaindanone ( 2 ). Notably, transformation rhoda‐1‐indanone rhoda‐2‐indanone was achieved for first time. comparision, reactivity IrCl(PPh and Ir(CO)(CH CN)(PPh ⋅ BF 4 towards affords irida‐2‐indanone fused iridacycles 5 ), respectively. These newly prepared coumpounds represent metellacycles resulting from between rhodium/iridium may provide further insights into catalytic processes involving synthesizing compounds.

Language: Английский

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Bismuth(III) triflate: an economical and environmentally friendly catalyst for the Nazarov reaction

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 1167 - 1178

Published: May 21, 2024

We describe the use of bismuth(III) triflate as an efficient and environmentally friendly catalyst for Nazarov reaction aryl vinyl ketones, leading to synthesis 3-aryl-2-ethoxycarbonyl-1-indanones 3-aryl-1-indanones. By changing temperature time, it was possible modulate reactivity, allowing two distinct product classes (3-aryl-2-ethoxycarbonyl-1-indanones 3-aryl-1-indanones) in good excellent yield. The did not require additives insensitive both air moisture. Preliminary biological evaluation some indanones showed a promising profile against human cancer line cells.

Language: Английский

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