Base‐Mediated [4+1] Annulation Strategy for Modular Assembly of Alkynyl/Carboxylated Dihydrobenzofurans

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 17, 2025

Abstract An efficient and operational [4+1] annulation strategy toward functional dihydrobenzofurans from 2‐bromomalonates in situ generated alkynyl o ‐quinone methides (from ‐hydroxyphenyl propargylamines) has been developed. Without the need for pre‐dried solvent inert atmosphere protection, a broad range of substituted propargylamines are well‐tolerated, producing expected alkynyl/carboxylated with good to high yields. Furthermore, gram‐scale synthesis valuable alkenyl/carboxylated construction were conducted provide great potential value medicinal chemistry other related disciplines.

Language: Английский

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Controllable stepwise fluorine elimination strategy for the chemodivergent synthesis of pyrido[2,1-a]isoquinolines

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: March 1, 2025

Language: Английский

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Synthesis of versatile fluorescent Isoquinolinium salts and their applications

Journal of Materials Chemistry B, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Isoquinolinium salts are well-known N-heterocyclic cationic compounds that have been applied in various research fields, such as materials chemistry and pharmaceutical applications. In particular, isoquinolinium with polyaromatic structures widely investigated due to their intrinsic photophysical properties, including fluorescence emission maxima, lifetime, quantum yield. Notably, fluorescent synthesized via synthetic strategies, alkylation of isoquinoline, oxidation dihydropyridines, rearrangement reactions, transition-metal-catalyzed C-H activation. this review, we summarize the methodologies for diverse applications applications, chemistry, theranostics, DNA binding, sensing, bioimaging.

Language: Английский

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Oxidative [4+2] Annulation of Pyrrole‐2‐carbaldehyde Derivatives with o‐Hydroxyphenyl Propargylamines: Syntheses of 5,6,7‐Trisubstituted Indolizines

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(63)

Published: Aug. 23, 2024

Abstract A base promoted oxidative [4+2] annulation of pyrrole‐2‐carbaldehyde derivatives with o ‐hydroxyphenyl propargylamines for the synthesis highly substituted indolizines has been developed. Using DBN as base, a broad range 5,6,7‐trisubstituted have prepared in good to excellent yields under mild conditions, and many useful functional groups can be tolerated.

Language: Английский

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Copper-Catalyzed Three-Component Tandem Cyclization for One-Pot Synthesis of Indole-Benzofuran Bis-Heterocycles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 22, 2024

A one-pot, three-component synthesis of indole-benzofuran bis-heterocycles from terminal alkynes, salicylaldehydes, and indoles has been developed via copper-catalyzed tandem annulation. This catalytic system utilizes readily available starting materials, enabling predictable with broad substrate versatility, excellent regiocontrol, gram-scale amenability. The reaction proceeds a sequential pathway involving A3 coupling, 1,4-conjugate addition, 5-exo-dig cyclization.

Language: Английский

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Solvent-Controlled Diastereodivergent Synthesis of Hexahydropyrrolo[2,1-a]isoquinolines through Pd/C-Catalyzed Dehydrogenative [3 + 2] Cycloaddition

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 10, 2024

A Pd/C-catalyzed dehydrogenative [3 + 2] cycloaddition is described for the diastereoswitchable synthesis of hexahydropyrrolo[2,1-a]isoquinolines by altering solvents. The reaction proceeds through a sequential formation azomethine ylides from tetrahydroisoquinoline acetates and 1,3-dipolar with 2-nitroethenylbenzenes. This method displayed tunable diastereoselectivity, broad substrate scope good functional group compatibility. Moreover, gram-scale selective reductive or oxidative transformations product further demonstrate utility this methodology.

Language: Английский

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NaHCO3‐promoted Formal [4+3] Annulation of Salicylaldehydes with Isoquinolinium Salts Accessing Isoquinoline‐fused Benzo[f][1,3]oxazepines

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 14, 2024

Abstract A concise and practical sustainable strategy for modular access to isoquinoline‐fused benzo[ f ][1,3]oxazepine derivatives through a formal [4+3] annulation of commercially available salicyaldehydes with isoquinolinium salts has been developed. The reactions proceeded the formation two new bonds (C=C C−O) seven‐membered heterocyclic ring in one pot. Remarkably, use simple NaHCO 3 as mild base, open atmosphere, nonhazardous reagents, nice functional group tolerance, easily scale up are added characteristics this approach. wide range substrates compatible reaction system, thereby proving facile reliable protocol constructing skeletons.

Language: Английский

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