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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Electrocatalytic Annulation–Iodosulfonylation of Indole‐Tethered 1,6‐Enynes to Access Pyrrolo[1,2‐a]indoles

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(10)

Published: Jan. 9, 2024

Abstract We present the first example of electrocatalytic three‐component annulation–iodosulfonylation indole‐tethered 1,6‐enynes with arylsulfonyl hydrazides and KI for accessing various iodosulfonated pyrrolo[1,2‐ a ]indoles in moderate to excellent yields high stereospecificity. This electrosynthesis opens new avenues construction skeleton good functional group compatibility under environmentally benign condition. Based on control experiments cyclic voltammetry data, we suggested plausible reaction mechanism which included anodic oxidation, homolysis iodide, radical addition, 5 ‐ exo dig cyclization, coupling or nucleophilic attack iodide ions cascade.

Language: Английский

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A Domino Dearomative ipso-Annulation/Desymmetrization Approach: Stereoselective Access to Tricyclic Alkaloid Skeletons

Organic Letters, Journal Year: 2024, Volume and Issue: 26(23), P. 4904 - 4909

Published: June 5, 2024

Herein, we reveal an unprecedented domino annulation of

Language: Английский

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Thiolative Annulation of N-Benzyl-N-cyanopropiolamides Leading to Divergent Synthesis of Pyrroloquinazolin-1-ones and Maleimides

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 8, 2025

An unprecedented successive radical-promoted thiolative annulation/Pd-catalyzed C-H amination of N-benzyl-N-cyanopropiolamides to access pyrrolo[2,1-b]quinazolin-1(9H)-ones in a one-pot manner is described. Moreover, altering the step with oxidation (reagent switch) offered maleimides from same set readily accessible precursors. Both transformations display versatility across wide range substrates, enabling efficient various functionalized quinazolin-1-ones and good yields.

Language: Английский

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Access to N-Fused Quinazolinones by Radical-Promoted Cascade Annulations of Alkenyl N-Cyanamides with Aromatic Aldehydes

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 7115 - 7124

Published: May 1, 2024

A cascade radical cyclization of alkenyl N-cyanamides with aromatic aldehydes has been achieved for an expeditious synthesis keto-methylated dihydropyrrolo-quinazolinones. Benzoyl radicals, generated from aryl in the presence di-tert-butyl peroxide (DTBP), promoted domino annulations leading to distinctive functionalized quinazolinones good yields. In addition, robustness present protocol is validated by employing heterocyclic and natural product-based aldehydes.

Language: Английский

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Carbonylative Cyclization of Biaryl Enones with Aldehydes and Oxamic Acids

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(24), P. 4901 - 4911

Published: Jan. 1, 2024

An oxidative radical-promoted carbonylative cyclization strategy for the synthesis of phenanthren-9-(10

Language: Английский

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Iron-catalyzed cascade cyclization of diaryldiyn-3-ones with P(O)H compounds: a rapid method for accessing 10-phosphorylated benzo[b]fluorenones

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 4997 - 5002

Published: Jan. 1, 2024

The first iron-catalyzed cascade cyclization of diaryldiyn-3-ones with P(O)H compounds for the synthesis 10-phosphorylated benzo[ b ]fluorenones is presented.

Language: Английский

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Manganese(iii) acetate in organic synthesis: a review of the past decade

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6850 - 6917

Published: Jan. 1, 2024

In this review, we summarize the latest developments and applications of Mn(OAc) 3 in organic synthesis over past decade, focusing on efforts to achieve milder reaction conditions while expanding scope possibilities.

Language: Английский

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Manganese(III) Acetylacetonate

Encyclopedia of Reagents for Organic Synthesis, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 6

Published: April 18, 2024

Abstract image [ 14284‐89‐0 ] C 15 H 21 MnO 6 (MW 352.30) InChI = 1S/3C5H8O2.Mn/c3*1‐4(6)3‐5(2)7;/h3*3,6H,1‐2H3;/q;;;+3/p‐3/b3*4‐3‐; InChIKey HYZQBNDRDQEWAN‐LNTINUHCSA‐K (one‐electron oxidant used to oxidize phenols, β‐dicarbonyl compounds, and thiols the corresponding radical) Physical Data : lustrous brown crystalline solid; mp 172 °C. 1 Solubility slightly sol water; acetone, benzene, chloroform, ether, ethanol, ethyl acetate.

Language: Английский

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