Recent Advances in Cyclization Reactions of 1,6‐Enynes

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1220 - 1268

Published: Jan. 22, 2024

Abstract Elaborated molecular architectures, specifically those bearing one or more carbon stereocenters, stand as an important class of carbocyclic and heterocyclic frameworks because they are frequently occurring core structures in numerous natural products biologically active pharmaceutical molecules. Over the past few decades, development versatile synthetic approaches via cascade cyclization reactions 1,6‐enynes for construction a series fused spiro compounds has been focus great deal research initiatives. These synthesis strategies peculiarly fascinating context assembly wide array molecules, products, agrochemicals, functional materials. In this review, recent developments transformations with diverse coupling reagents summarized since 2018, which could be divided into five categories: 1) Introduction; 2) Transition metal catalyzed 1,6‐enynes; 3) Metal‐free 4) Visible‐light‐induced 5) Electrocatalytic 1,6‐enynes.

Language: Английский

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Metal-Catalyst-Free Radical Cyclization of 1,6-Enynes for the Selective and Switchable Synthesis of Lactams in Water

ACS Sustainable Chemistry & Engineering, Journal Year: 2022, Volume and Issue: 10(18), P. 6057 - 6062

Published: April 27, 2022

Three types of novel radical cyclization 1,6-enynes with sulfonyl hydrazides have been presented, which provided convenient synthetic approaches for accessing five-membered cyclic lactams, lactams containing C–I bond, and six-membered lactams. Notably, these transformations are implemented in metal-catalyst-free systems, three classes important lactam derivatives were synthesized selectivity controllability from the same substrate using water as green solvent.

Language: Английский

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Visible-Light-Mediated Three-Component Radical Iodosulfonylative Cyclization of Enynes

Organic Letters, Journal Year: 2022, Volume and Issue: 24(13), P. 2515 - 2519

Published: March 30, 2022

An efficient three-component radical iodosulfonylative cyclization of enynes is described. The visible-light irradiation iodoform with sulfinates enables sulfonyl generation under catalyst- and oxidant-free conditions triggers the addition, iodination cascade reactions, giving various vinyl iodide containing sulfones in moderate to good yields.

Language: Английский

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Photocatalytic Bicyclization of Indole-Tethered 1,6-Enynes for Diastereoselective Synthesis of Pyrrolo[3,2,1-jk]carbazoles

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3810 - 3815

Published: April 28, 2024

A visible-light-driven photocatalytic protocol is established for the diastereoselective synthesis of pyrrolo[3,2,1-jk]carbazoles via a radical-triggered multicomponent bicyclization reaction starting from readily available indole-tethered 1,6-enynes and α-benzyl-α-bromomalonates under mild conditions. This approach exhibits wide substrate compatibility excellent tolerability toward various functional groups boasts benefit efficient ring formation chemical bond creation.

Language: Английский

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Oxidative Cyclization of Aryl Ynones with NaNO₂ for the Divergent Synthesis of NO₂‐Containing Spiro[5.5]trienones, Indenones and Thioflavones

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(21), P. 3651 - 3656

Published: Sept. 21, 2022

Abstract A K 2 S O 8 ‐promoted nitration/spirocyclization of biaryl ynones using inexpensive NaNO as nitro source has been described. This cascade reaction is triggered by nitration alkyne and followed 6‐exo‐trig spirocyclization, dearomatization, forming the NO ‐containing spiro[5.5]trienones in 63–85% yields. The present also provides a practical method for synthesis nitrated indenones thioflavones with 58–85% magnified image

Language: Английский

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Visible Light‐Mediated Manipulation of 1,n‐Enynes in Organic Synthesis

ChemCatChem, Journal Year: 2022, Volume and Issue: 14(14)

Published: May 2, 2022

Abstract The 1, n ‐enynes are potent scaffolds in organic synthesis, providing a state‐of‐the‐art approach for synthesizing various acyclic and carbo‐ heterocyclic compounds. Radical cascade cyclization C−H functionalization of have gained immense attention the synthetic community. Significant advancement this field has been developed over years, employing harsh expensive metal catalysts usually associated with intense product purification unwanted side‐products. In context, advent visible light photocatalysis as mild efficient area is welcome step. Herein, we provide an exclusive overview recent developments light‐assisted manipulation ‐enynes. We classified review into 1,3‐, 1,4‐, 1,5‐, 1,6‐, 1,7‐, 1,8‐enynes, well dienyne, enediyne‐based reactions.

Language: Английский

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Photoinduced Construction of Thieno[3,4-c]quinolin-4(5H)-ones/Selenopheno[3,4-c]quinolin-4(5H)-ones Using Diphenyl Disulfide or Diphenyl Diselenide as Sulfur or Selenium Sources

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 88(2), P. 828 - 837

Published: Dec. 28, 2022

A photocatalytic synthesis of thieno[3,4-c]quinolin-4(5H)-ones/selenopheno[3,4-c]quinolin-4(5H)-ones using diphenyl disulfide or diselenide as sulfur selenium sources was developed. Two C-S/Se bonds and one C-C bond were constructed simultaneously without transition metals other additives.

Language: Английский

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Difunctionalization of Dienes, Enynes and Related Compounds via Sequential Radical Addition and Cyclization Reactions

Molecules, Journal Year: 2023, Volume and Issue: 28(3), P. 1145 - 1145

Published: Jan. 23, 2023

Radical reactions are powerful in creating carbon–carbon and carbon–heteroatom bonds. Designing one-pot radical with cascade transformations to assemble the cyclic skeletons two new functional groups is both synthetically operationally efficient. Summarized this paper recent development of involving addition cyclization dienes, diynes, enynes, as well arene-bridged arene-terminated compounds for preparation difunctionalization compounds. Reactions carried out initiators, transition metal-catalysis, photoredox, electrochemical conditions included.

Language: Английский

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Photoinduced Copper-Catalyzed 1,2-Difunctionalization of 1,3-Dienes with Aryl Diselenides

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(22), P. 15969 - 15974

Published: Oct. 30, 2023

Described herein is a photoinduced copper-catalyzed 1,2-difunctionalization of 1,3-dienes. The selenium atom radical was generated by the visible light irradiation diselenides, triggering addition with 1,3-dienes to form allyl intermediate. Subsequent rapid Z/E isomerization allowed for thermodynamically favorable intermediate formation and enabled copper catalyzed stereoselective functionalization various nucleophiles.

Language: Английский

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Palladium-Catalyzed Carbo-Aminative Cyclization of 1,6-Enynes: Access to Napthyridinone Derivatives

Organic Letters, Journal Year: 2022, Volume and Issue: 24(8), P. 1598 - 1603

Published: Feb. 22, 2022

1,6-Enynes have recently stimulated enormous attention toward paving the way to unique cascade cyclizations offering complex cyclic motifs from linear substrates. We describe herein a general approach napthyridinones via Pd-catalyzed annulation of 1,6-enynes with 2-iodoanilines. This protocol represents rare carbo-aminative annulative cyclization 6-endo-trig mode, subduing well-documented exo-trig/dig cyclizations. The regioselective aryl palladation alkyne followed by Heck-type intramolecular coupling before isomerization were key in realizing this cascade.

Language: Английский

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