Access to thiionized-, selenolized-, and alkylated 5-alkylidene 3-pyrrolin-2-one derivatives via a regioselective oxidative annulation reaction DOI
Donghan Liu, Siyu Song,

Longkun Chen

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(12), P. 2596 - 2602

Published: Jan. 1, 2023

A metal-free regioselective oxidative annulation reaction of readily available 2,4-pentanediones with primary amines has been described. This protocol provides a divergent strategy for the incorporation various radical donors into 5-alkylidene 3-pyrrolin-2-one skeletons, producing variety thiionized-, selenolized-, and alkylated derivatives. Moreover, diverse synthetic transformations products were also investigated.

Language: Английский

Three-component synthesis ofN-naphthyl pyrazolesviaRh(iii)-catalyzed cascade pyrazole annulation and Satoh–Miura benzannulation DOI

Demao Chen,

Liyun Zhou,

Yunyun Liu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(27), P. 4036 - 4039

Published: Jan. 1, 2023

The synthesis of N-naphthyl pyrazoles has been realized by the direct three-component reactions enaminones, aryl hydrazine hydrochlorides and internal alkynes via Rh(III) catalysis. synthetic employing simple substrates lead to simultaneous construction dual cyclic moieties, including a pyrazole ring phenyl ring, sequential formation two C-N three C-C bonds.

Language: Английский

Citations

33

Silver‐catalyzed Cascade Bis‐heteroannulation Reaction of Enynones and o‐Hydroxyphenyl Enaminones: Access to Highly Functionalized 3‐Furylmethyl Chromones DOI

Mingshuai Zhang,

Meichen Liu,

Yuetong Qiu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2363 - 2369

Published: March 16, 2024

Abstract A synthetic protocol was developed to synthesize highly functionalized 3‐furylmethyl chromones from enynones and o ‐hydroxyphenyl enaminones via silver‐catalyzed cascade bis‐heteroannulation reaction. This strategy features broad substrate scope good functional group tolerance. Furthermore, the chromone skeleton shows potential application value through further gram‐scale synthesis derivatization.

Language: Английский

Citations

13

Selective synthesis of pyridazin-fused chromones and 3-pyridazinyl chromones through intermolecular chromone annulation of o-hydroxyphenylenaminones with aryldiazonium salts DOI
Siyu Song,

Zhilai Zhang,

Menglin Peng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 3906 - 3912

Published: Jan. 1, 2024

A chemodivergent and skeleton-controllable annulation reactions of readily available o -HPEs aryldiazonium salts was described for the synthesis highly functionalized pyridazine-fused chromones with high antiviral activity higher safety.

Language: Английский

Citations

11

Photocatalytic C–H Thiocyanation of NH2-Enaminones and the Tunable Synthetic Routes to 2-Aminothiazoles and 2-Thiazolinones DOI

Junlong Zeng,

Jie‐Ping Wan, Yunyun Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(19), P. 13195 - 13203

Published: Sept. 15, 2022

Visible light photocatalytic reactions of NH2-enaminones and ammonium thiocyanate for chemoselective α-C-H thiocyanation have been realized the first time, providing a sustainable route synthesis thiocyanated NH2-enaminones. In addition, enaminone products can be flexibly transformed into 2-aminothiazoles 2-thiazolinones via simple operation.

Language: Английский

Citations

30

Copper‐Catalyzed Oxidative [1+2+1+2] Cascade Cyclization of N,N‐Dimethyl Enaminones with Benzylamines: A Facile Access to Functionalized 1,4‐Dihydropyridines DOI

Yulin Sun,

Zhangmengjie Chai,

Donghan Liu

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(28)

Published: Feb. 24, 2023

Using benzylamines as the C4 source of 1,4-dihydropyridines (1,4-DHPs), a Cu-catalyzed oxidative [1+2+1+2] cascade cyclization for synthesis 1,4-DHPs was firstly developed. A broad range easily available N,N-dimethyl enaminones and are employed smoothly to provide diverse with high efficiency. This method is performed by one-pot C(sp3 )-H bond functionalization/C(sp3 )-N cleavage/cyclization strategy form simultaneously two )-C(sp2 ) bonds, C(sp2 1,4-DHP ring.

Language: Английский

Citations

19

Transition‐Metal‐Free C(sp2)−H Phosphorothiolation/Cyclization of o‐Hydroxyarylenaminones: Access to S‐3‐Chromon Phosphorothioates DOI
Biao Zhang,

Zhonghui Fu,

Haoqi Yang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(9), P. 1602 - 1606

Published: March 19, 2022

Abstract The C( sp 2 )−H phosphorothiolation involving cyclization process through a transition‐metal‐free strategy is reported. It provides an attractive approach for the construction valuable S ‐3‐chromon phosphorothioates from o ‐hydroxyarylenaminones and P(O)SH compounds in presence of 1.0 equiv. iodine at 60 °C. This novel protocol shows readily available chemicals, broad substrate scope, mild reaction conditions. magnified image

Language: Английский

Citations

26

Rh(iii)-catalyzed cascade annulation reaction of N,N-dimethyl enaminones with iodonium ylides to give substituted isocoumarins DOI

Mingshuai Zhang,

Longkun Chen,

Donghan Liu

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(26), P. 12274 - 12278

Published: Jan. 1, 2023

A wide variety of isocoumarin derivatives are easily constructed via a Rh( iii )-catalyzed C–H bond activation/annulation cascade reaction.

Language: Английский

Citations

14

Metal-free enaminone C–N bond cyanation for the stereoselective synthesis of (E)- and (Z)-β-cyano enones DOI
Ting Liu, Jie‐Ping Wan, Yunyun Liu

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(72), P. 9112 - 9115

Published: Jan. 1, 2021

The C–N bond cyanation of tertiary enaminones has been realized for the stereoselective synthesis both ( E )- and Z )-β-cyano enones under mild metal-free conditions, providing highly practical approaches β-cyano enones.

Language: Английский

Citations

31

Synthesis of Functionalized 3‐(1H‐Isochromen)‐chromones via Ag2O‐Catalyzed Cascade Cyclization Reaction of o‐Hydroxyarylenaminones with o‐Alkynylbenzaldehydes DOI

Mingshuai Zhang,

Zhuoyuan Liu,

Longkun Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(24), P. 4440 - 4446

Published: Dec. 2, 2022

Abstract A silver‐catalyzed protocol for the synthesis of 3‐(1 H ‐isochromen)‐chromones is described. The method involves an initial 6‐endo‐dig cyclization o ‐alkynylbenzaldehydes and domino C−H alkylation chromone annulation ‐hydroxyarylenaminones, which enables installation 1 ‐isochromen in a single structure. This synthetic strategy advantageous excellent regioselectivity, step economy, concise one‐pot methodology, gram‐scale synthesis, as well high bond‐forming efficiency. magnified image

Language: Английский

Citations

22

Fe(OTf)3-catalyzed annulation of α,β-unsaturated ketoxime acetates with enaminones for the synthesis of functionalized 2,4-diarylpyridines DOI

Xing-Mei Hu,

Jing Yang,

Jia-Ming Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(17), P. 4298 - 4304

Published: Jan. 1, 2023

This method involves a cascade reaction utilizing 1 and enamines 2 as substrates, which occurred by refluxing mixture of the starting materials in toluene with catalyst Fe(OTf) 3 .

Language: Английский

Citations

12