Base‐Promoted Synthesis of 3‐Alkenyl‐2‐pyridones from N‐Propargyl‐β‐enaminones and Aryl Aldehydes DOI

Qingyu Tian,

Shangyun Xiao,

Guolin Cheng

et al.

Chinese Journal of Chemistry, Journal Year: 2021, Volume and Issue: 39(10), P. 2781 - 2788

Published: June 27, 2021

Main observation and conclusion In this article, we report a base‐promoted sequential cyclization/aldol‐type condensation/isomerization cascade reaction of N ‐propargyl‐β‐enaminones with aryl aldehydes. The key step in protocol is the generation 1,4‐oxazepine anions from under basic conditions, which are captured by method allows formation one pyridone core C—C double bond “one pot”, preparation variety densely decorated derivatives moderate to good yields broad functional group tolerance.

Language: Английский

The clean preparation of multisubstituted pyrroles under metal- and solvent-free conditions DOI
Qingwen Gui, Xiaoli He, Wenjing Wang

et al.

Green Chemistry, Journal Year: 2019, Volume and Issue: 22(1), P. 118 - 122

Published: Nov. 29, 2019

A practical method for the clean preparation of multisubstituted pyrroles via an iodine-catalyzed multicomponent reaction under metal- and solvent-free conditions was developed. In gram-scale synthesis, can be easily collected through simple extraction.

Language: Английский

Citations

75

Ruthenium(ii)-catalyzed chemoselective deacylative annulation of 1,3-diones with sulfoxonium ylides via C–C bond activation DOI Creative Commons

Si Wen,

Weiwei Lv,

Dan Ba

et al.

Chemical Science, Journal Year: 2019, Volume and Issue: 10(39), P. 9104 - 9108

Published: Jan. 1, 2019

Highly chemoselective Ru(ii)-catalyzed deacylative annulation of 1,3-diones with sulfoxonium ylides was achieved to afford (hetero)aryl substituted furans.

Language: Английский

Citations

51

Ultrasound-assisted tandem synthesis of tri- and tetra-substituted pyrrole-2-carbonitriles from alkenes, TMSCN and N,N-disubstituted formamides DOI
Qingwen Gui, Fan Teng,

Sheng-Neng Ying

et al.

Chinese Chemical Letters, Journal Year: 2020, Volume and Issue: 31(12), P. 3241 - 3244

Published: July 9, 2020

Language: Английский

Citations

40

Ruthenium(II)-Catalyzed Construction of Isocoumarins via Dual C–H/C–C Activation of Sulfoxonium Ylides DOI

Si Wen,

Yanhui Chen,

Zemin Zhao

et al.

The Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 85(2), P. 1216 - 1223

Published: Dec. 6, 2019

A ruthenium(II)-catalyzed annulation between two molecules of sulfoxonium ylides is achieved, generating a variety substituted isocoumarins in reasonable yields. This strategy features dual C–H/C–C activation one pot and has wide substrate scope good functional group tolerance.

Language: Английский

Citations

40

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

Tunable Synthesis of 4-Acyl- and 4-Formyl Pyrroles by Rhodium-Catalyzed Ring-Expansion of Azirines with Enaminones DOI
Xiuli Li, Jianchao Liu, Jie‐Ping Wan

et al.

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

Published: Feb. 19, 2025

A rhodium-catalyzed annulation of 2H-azirines with enaminones is presented. This protocol affords a convenient approach to the diversity-oriented synthesis 4-acyl- and 4-formyl pyrroles good functional group tolerance. The utility this reaction has been demonstrated by scale-up preparation, late-stage modification natural molecules, diverse derivatives.

Language: Английский

Citations

0

Synthesis of Tetrasubstituted Pyrroles via DBU-Mediated Cyclization of Unactivated Propargyl Tertiary Amines DOI
Pengyu Zhou, Tiantian Zhang, Q. Richard Lu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 10, 2025

Compared with the well-developed cyclization of functionalized propargylamines, use unactivated tertiary propargylamines to access pyrroles remains challenging. Herein, we report an efficient method for constructing tetrasubstituted via a DBU-mediated intramolecular cycloaddition N-alkyl propargylamines. This reaction employs dihydropyrrole intermediates, followed by oxidation produce in presence 2,3-dichloro-5,6-dicyano-p-benzoquinone. In addition, broad substrate scope, high atom economy, selectivity, and simple operation are also advantages this protocol.

Language: Английский

Citations

0

Copper-Catalyzed Three-Component Cascade Michael Addition/Heck-Type Alkylation/Annulation: Accessing Fully Substituted 1,3-Dihydro-2H-pyrrol-2-ones DOI

Dan Ba,

Yanhui Chen,

Weiwei Lv

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(21), P. 8603 - 8606

Published: Oct. 15, 2019

We report a highly efficient copper-catalyzed three-component reaction of alkylamines, acetylenedicarboxylates, and α-bromocarbonyls for the assembly fully substituted 1,3-dihydro-2H-pyrrol-2-ones. A variety alkylamines ammonium salt are functionalized with acetylenedicarboxylates α-bromocarbonyls. N-aryl enaminoesters also successfully alkylated This protocol is understood to proceed through radical Heck-type coupling in-situ-generated bulky trisubstituted alkenes tertiary alkyl bromides, which realized first time.

Language: Английский

Citations

33

AuCl3‐Catalyzed Ring‐Closing Carbonyl–Olefin Metathesis DOI
Rui Wang, Yi Chen, Mao Shu

et al.

Chemistry - A European Journal, Journal Year: 2019, Volume and Issue: 26(9), P. 1941 - 1946

Published: Dec. 23, 2019

Abstract Compared with the ripeness of olefin metathesis, exploration construction carbon–carbon double bonds through catalytic carbonyl–olefin metathesis reaction remains stagnant and has received scant attention. Herein, a highly efficient AuCl 3 ‐catalyzed intramolecular ring‐closing is described. This method features easily accessible starting materials, simple operation, good functional‐group tolerance short times, provides target cyclopentenes, polycycles, benzocarbocycles, N‐heterocycle derivatives in to excellent yields.

Language: Английский

Citations

33

Synthesis of 3-(2-quinolyl) chromones from ynones and quinolineN-oxidesviatandem reactions under transition metal- and additive-free conditions DOI
Jing Liu,

Dan Ba,

Yanhui Chen

et al.

Chemical Communications, Journal Year: 2020, Volume and Issue: 56(29), P. 4078 - 4081

Published: Jan. 1, 2020

A novel method for the synthesis of 3-(2-quinolyl) chromones through a tandem [3+2] cycloaddition/ring-opening/O-arylation from ynones and quinoline N-oxides has been developed. This protocol proceeds under transition metal- additive-free conditions can be amplified to gram level in 91% yield. 3-(1-Isoquinolyl) 3-(2-pyridyl) are also successfully synthesized using isoquinoline pyridine basic conditions. Various heteroarene-contaning were afforded 30-98% yields, which difficult obtained compounds interest pharmaceutical chemistry chemical biology.

Language: Английский

Citations

26