Transition-metal-free approach to quinolines via direct oxidative cyclocondensation reaction of N,N-dimethyl enaminones with o-aminobenzyl alcohols DOI Creative Commons

Kairui Rao,

Zhangmengjie Chai,

Pan Zhou

и другие.

Frontiers in Chemistry, Год журнала: 2022, Номер 10

Опубликована: Сен. 21, 2022

A transition-metal-free method for the construction of 3-substituted or 3,4-disubstituted quinolines from readily available N,N-dimethyl enaminones and o-aminobenzyl alcohols is reported. The direct oxidative cyclocondensation reaction tolerates broad functional groups, allowing efficient synthesis various in moderate to excellent yields. involves a C (sp3)-O bond cleavage C=N bind C=C formation during cyclization process, mechanism was proposed.

Язык: Английский

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

Demao Chen,

Liyun Zhou,

Yunyun Liu

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(27), С. 4036 - 4039

Опубликована: Янв. 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.

Язык: Английский

Процитировано

34

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

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(10), С. 2363 - 2369

Опубликована: Март 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.

Язык: Английский

Процитировано

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

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(14), С. 3906 - 3912

Опубликована: Янв. 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.

Язык: Английский

Процитировано

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

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(19), С. 13195 - 13203

Опубликована: Сен. 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.

Язык: Английский

Процитировано

31

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

и другие.

Chemistry - A European Journal, Год журнала: 2023, Номер 29(28)

Опубликована: Фев. 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.

Язык: Английский

Процитировано

20

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

Zhonghui Fu,

Haoqi Yang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(9), С. 1602 - 1606

Опубликована: Март 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

Язык: Английский

Процитировано

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

и другие.

New Journal of Chemistry, Год журнала: 2023, Номер 47(26), С. 12274 - 12278

Опубликована: Янв. 1, 2023

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

Язык: Английский

Процитировано

15

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

и другие.

Chemical Communications, Год журнала: 2021, Номер 57(72), С. 9112 - 9115

Опубликована: Янв. 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.

Язык: Английский

Процитировано

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

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(24), С. 4440 - 4446

Опубликована: Дек. 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

Язык: Английский

Процитировано

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

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(17), С. 4298 - 4304

Опубликована: Янв. 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 .

Язык: Английский

Процитировано

13