Photodriven Radical-Polar Crossover Cyclization Strategy: Synthesis of Pyrazolo[1,5-a]pyridines from Diazo Compounds

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2511 - 2516

Published: March 20, 2024

This work demonstrates the synthesis of a variety perfluoroalkyl heterocycles via visible-light-driven radical-polar crossover cyclization strategy. In this process, single-electron reduction/SNV-type/cyclization sequences follow radical addition reaction diazoester, which differs from current role diazoesters as precursors/acceptors. transformation excellent functional group compatibility and allows for modification many bioactive molecules with diazoesters. Such could represent novel approach to photochemical diazo compounds.

Language: Английский

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Electrochemical Enaminone-Thioamide Annulation and Thioamide Dimeric Annulation for the Tunable Synthesis of Thiazoles and 1,2,4-Thiadiazole

Organic Letters, Journal Year: 2024, Volume and Issue: 26(25), P. 5263 - 5268

Published: June 14, 2024

A green and sustainable electrochemical oxidative cyclization of enaminones with thioamides under metal- oxidant-free conditions has been developed, providing an efficient approach for thiazole synthesis. Furthermore, 1,2,4-thiadiazoles can be selectively accessed via the dimerization in absence enaminones.

Language: Английский

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Review of application of the I₂ and dimethyl sulfoxide combined reagent system to aryl methyl ketones for diverse transformations

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2665 - 2692

Published: Jan. 1, 2024

The synthesis of small molecules and complex scaffolds is one the most important topics in organic synthesis.

Language: Английский

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I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 36(1), P. 109799 - 109799

Published: March 20, 2024

Language: Английский

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Recent advances in iodine–DMSO mediated C(sp³)–H functionalization of methyl-azaarenes via Kornblum oxidation

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(17), P. 7614 - 7638

Published: Jan. 1, 2024

In the iodine–DMSO medium, methyl group of azaarenes is converted into aldehyde via Kornblum oxidation and trapped in situ by nucleophiles to create azaarene-linked functionalized scaffolds.

Language: Английский

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Photocatalytic Annulation of Enaminones with Thioureas for the Synthesis of 2-Aminothiazoles via Tandem C–S and C–N Bond Formation

Synthesis, Journal Year: 2024, Volume and Issue: 56(16), P. 2565 - 2571

Published: April 26, 2024

Abstract Visible-light photocatalytic reactions between enaminones and thioureas leading to thiazole products have been achieved. The annulation process consists of tandem C–S C–N bond formation by running under air atmosphere at ambient temperature. Broad substrate tolerance the sustainable protocol has verified practical synthesis divergent thiazoles with both monocyclic fused cyclic structures.

Language: Английский

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BPO-promoted [4 + 2] cyclization of enaminones and o-phenylenediamines to 2-acyl quinoxalines via a cascade transamination and C–H amination

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(20), P. 4067 - 4071

Published: Jan. 1, 2024

Rapid assembly of quinoxalines in a single step from readily available precursors has been recognized as an ideal platform terms efficiency and operation. Herein, we report BPO-promoted metal-free approach to 2-acyl enaminones

Language: Английский

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N-Benzylhydroxylamine as a novel synthetic block in “C1N1” embedding reaction via α-C(sp³)–H activation strategy

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(56), P. 7180 - 7183

Published: Jan. 1, 2024

A novel process using N -benzylhydroxylamine hydrochloride as a “C1N1 synthon” in [2+2+1] cyclization for the construction of 1,2,5-trisubstituted imidazoles has been described first time.

Language: Английский

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Divergent Synthesis of Enynals and Dihydrobenzo[f]isoquinolines via Deoxyalkynylation of Enaminones Enabled by the Cooperative Action of Tf₂O/Pd/Cu

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16419 - 16425

Published: Oct. 28, 2024

A variety of enynals and dihydrobenzo[

Language: Английский

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I₂–DMSO‐Mediated Multicomponent [2+1+1+1] Annulation Reaction via Ethyl Nitroacetate C—NO₂ Bond Cleavage as a C1 Synthon: A Route to Multisubstituted β‐Pyrrolidinones Derivatives with a Quaternary Center

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(17), P. 2029 - 2034

Published: April 29, 2024

Comprehensive Summary A [2 + 1 1] cyclization reaction has been developed for the synthesis of multisubstituted β ‐pyrrolidinones from commercially available aryl methyl ketones, primary amines, and ethyl nitroacetate. In this I 2 –DMSO‐meditated process, C—NO bond nitroacetate is cleaved, affording a C1 synthon, formation two C—C C—N bonds quaternary carbon center are constructed in one pot. This method good substrate compatibility permits late‐stage modification pharmaceutical compounds.

Language: Английский

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