Photocatalyzed Selective Hydrocarbonation of Alkenes with Hantzsch Esters toward 4-Alkyl-Hantzsch Esters DOI

Shiqin Qiu,

Huaixuan Guo,

Peng Xu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6730 - 6735

Published: July 30, 2024

Here, we describe a mild photoredox-neutral reaction system that enables the selective hydrocarbonation of alkenes with Hantzsch esters, affording structurally diverse 4-alkyl-Hantzsch esters. This straightforward protocol can be performed under an air atmosphere without need for any transition metals. The synthetic potential this method is well exemplified by late-stage structural modification series pharmaceutically relevant complex molecules.

Language: Английский

Oxidative Free-Radical C(sp2)–H Bond Chlorination of Enaminones with LiCl: Access to Highly Functionalized α-Chlorinated Enaminones DOI

Yunhua Xie,

Zhilai Zhang,

Biao Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8521 - 8530

Published: June 3, 2024

An oxidative free-radical C(sp2)–H bond chlorination strategy of enaminones has been developed by using LiCl as a chlorinating reagent and K2S2O8 an oxidant. This transformation provides new straightforward synthetic methodology to afford highly functionalized α-chlorinated with Z-configuration in good excellent yields.

Language: Английский

Citations

6
Additive-Free Construction of Tetrahydropyrimidine Skeleton by using 1,3,5-Triazinane as Four-Atom Synthon DOI

Lanlan Rong,

Jingwen Ma,

Chenru Lai

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(13), P. 9496 - 9501

Published: June 18, 2024

Herein, an unprecedented [4 + 2] cycloaddition of enaminone with 1,3,5-triazinane has been developed. The representative semihydrogenated aromatic heterocycle 1,2,3,4-tetrahydropyrimidines have synthesized a broad substrate scope, demonstrating potential antitumor activity. This approach smoothly conducted under additive-free and environmentally friendly conditions that are compatible various functional groups. Furthermore, the condition optimization process reveals tetrahydropyrimidine product is regulated via reaction temperature.

Language: Английский

Citations

2
Iron-Catalyzed [2+1+2+1] Annulation of Amines and N,N-Dimethyl Enaminones using N,N-Dimethylaminoethanol as a One-Carbon Synthon for the Synthesis of 1,4-Dihydropyridines DOI
Jianyong Yuan,

Wanqian Ma,

Qiulin Kuang

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(12), P. 1932 - 1940

Published: Jan. 9, 2024

Abstract A simple and efficient method for the synthesis of 1,4-dihydropyridines from amines, N,N-dimethyl enaminone N,N-dimethylaminoethanol in a four-component [2+1+2+1] annulation catalyzed by FeCl3 has been established, where was applied as methine source. The procedure executed smoothly, resulting wide range with moderate to good yields. Additionally, these fluorophores exhibited photophysical characteristics.

Language: Английский

Citations

1
DBU‐Promoted Solvent‐Free One‐Pot Multicomponent Synthesis of 2‐Amino‐1,4‐Dihydropyridines From β‐Enaminones, Aromatic Aldehydes and Malononitrile DOI

Saikrishna Chintha,

Nagaraju Medishetti,

Maneesha Karangi

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(28)

Published: July 23, 2024

Abstract The synthesis of 2‐amino‐1,4‐dihydropyridines was accomplished starting from β‐enaminones, aromatic aldehydes and malononitrile with DBU without solvent. reaction proceeds through a Knoevenegel condensation, which affords the benzylidine olefin intermediate. This can directly react β‐enaminone, leading to desired product. Simple conditions no solvent good yields are advantages this protocol.

Language: Английский

Citations

1
Montmorillonite K-10 catalyzed synthesis of Hantzsch dihydropyridine derivatives from methyl arenes via in situ generated ammonia under microwave irradiation in neat conditions DOI Creative Commons
Vishal Singh,

Khushbu Rajput,

Sundaram Singh

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(37), P. 27086 - 27091

Published: Jan. 1, 2024

Solvent-free synthesis of Hantzsch 1,4-dihydropyridine catalyzed by montmorillonite K-10 involves oxidation methyl arenes and in situ -generated ammonia from urea hydrogen peroxide under microwave irradiation.

Language: Английский

Citations

1
Nucleophilic Dearomatization of Activated Pyridines Using Vinyl Sulfoxonium Ylides: Application to the Synthesis of Bis-Heterocycles DOI

Srashti Bhardwaj,

Dinesh Kumar Gopalakrishnan,

Tarak Karmakar

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 5, 2024

A highly efficient method has been developed for synthesizing 4-dienyl dihydropyridines through the nucleophilic dearomatization of activated pyridines using vinyl sulfoxonium ylides. This reaction follows sequence involving ylide addition to pyridine, [2,3]-sigmatropic rearrangement, and subsequent sulfenic acid elimination. The resulting are then used in synthesis substituted bis-heterocyles. Control experiments quantum chemical calculations were conducted elucidate selectivity mechanistic pathway.

Language: Английский

Citations

1
Photocatalyzed Selective Hydrocarbonation of Alkenes with Hantzsch Esters toward 4-Alkyl-Hantzsch Esters DOI

Shiqin Qiu,

Huaixuan Guo,

Peng Xu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6730 - 6735

Published: July 30, 2024

Here, we describe a mild photoredox-neutral reaction system that enables the selective hydrocarbonation of alkenes with Hantzsch esters, affording structurally diverse 4-alkyl-Hantzsch esters. This straightforward protocol can be performed under an air atmosphere without need for any transition metals. The synthetic potential this method is well exemplified by late-stage structural modification series pharmaceutically relevant complex molecules.

Language: Английский

Citations

0