One‐Pot Multicomponent Selective Synthesis of 5‐Trifluoromethyl Pyrimidine Derivatives DOI

Dingyuan Lou,

Yuxin Ding,

Zhening Jin

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2715 - 2720

Published: May 9, 2024

Abstract A one‐pot multi‐component reaction strategy for the selective synthesis of 5‐trifluoromethyl pyrimidine derivatives has been established. This method avoids inherent selectivity challenges in direct trifluoromethylation. The demonstrates tolerance to various functional groups, yielding with up 80% yields. Moreover, practicality this underscored through scale‐up reactions.

Language: Английский

Radical-Polar Crossover Enabled Triple Cleavage of CF2Br2: A Multicomponent Tandem Cyclization to 3-Fluoropyrazoles DOI

Wanqing Zuo,

Lingling Zuo,

Xiao Geng

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(32), P. 6062 - 6066

Published: Aug. 8, 2023

The elaboration of step-economy and catalytic approaches for accessing diverse fluorinated heterocyclics is highly desirable. Described herein a radical-polar crossover enabled three-component cyclization to polysubstituted fluoropyrazoles by using CF2Br2 as novel C1F1 synthon. Mechanistic experiments revealed that the in situ generation reactive intermediate gem-difluorovinylimine ion key this transformation. This protocol unlocks reactivity adds significant synthetic values fluorine chemistry.

Language: Английский

Citations

64
A Strategy for Accessing Trifluoromethyl Carbinol-Containing Chromones from o-Hydroxyaryl Enaminones and Trifluoroacetaldehyde/Ketone Derivatives DOI
Siyu Pan, Mengshi Song,

Lingling Zuo

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5586 - 5596

Published: April 6, 2023

Herein, we present a practical strategy for the direct construction of structurally diverse trifluoromethyl carbinol-containing compounds, especially CF3-substituted tertiary alcohol with chromone derivatives from easily available o-hydroxyaryl enaminones and trifluoroacetaldehyde/ketone under metal-free conditions. This reaction features broad substrate scope good yields is scaled up. Notably, one-pot in two-steps obtained products amidines also developed to provide series multi-substituted pyrimidine bearing two unique hydroxyls one containing functional units.

Language: Английский

Citations

53
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
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 DOI
You Zhou, Li‐Sheng Wang,

Shuang‐Gui Lei

et al.

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

Published: March 20, 2024

Language: Английский

Citations

10
Rh(III)-Catalyzed Enaminone-Directed C–H Coupling with Diazodicarbonyls for Skeleton-Divergent Synthesis of Isocoumarins and Naphthalenes DOI
Wei-Ping Wu, Xuan Wu,

Shuaixin Fan

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(42), P. 7850 - 7855

Published: Oct. 19, 2022

Diversity-oriented synthesis is tremendously useful for expanding the explorable chemical space but restricted by limited available toolbox of skeleton-diversification chemistry. We report herein Rh(III)-catalyzed coupling enaminones and diazodicarbonyls skeleton-divergent isocoumarins naphthalenes. The diazodicarbonyl ring size pH dependence skeleton-forming process demonstrates achievement both substrate- reagent-controlled skeletal diversity generation in a single type system. An intriguing C–C bond cleavage reactivity critical enabling facile synthetic access to isocoumarins.

Language: Английский

Citations

37
Synthesis of homophthalimide spironaphthalenones through [5 + 1] spiroannulation of aryl/alkenyl enaminones with diazo homophthalimides DOI

Chun Xia Yang,

Xinying Zhang, Xuesen Fan

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(17), P. 4282 - 4288

Published: Jan. 1, 2023

Presented herein is a novel synthesis of homophthalimide spironaphthalenones from the cascade reaction enaminones with diazo homophthalimides.

Language: Английский

Citations

20
Switchable Multicomponent Cyclization Reactions to Access Fluoroalkylated Dihydropyrimidines and Pyrimidines under Solvent‐Free Conditions DOI

Wanqing Zuo,

Zhizhen Zhu, Yu Cheng

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(12), P. 1394 - 1398

Published: Feb. 23, 2024

Comprehensive Summary The development of switchable solvent‐free multicomponent reactions to build high‐value‐added products is an important demand for organic synthesis. Herein, we detailed the successful implementation a strategy construction diverse 4‐fluoroalkyl‐1,4‐dihydropyrimidines and 4‐fluoroalkyl‐pyrimidines via solvent/additive‐free [3 + 2 1] annulation, starting from readily available enamines, trifluoroacetaldehyde hydrate or 1‐ethoxy‐2,2‐difluoroethanol amidines hydrochloride. This reaction conforms concept green synthesis, provides new avenue access valuable fluorinated heterocycles.

Language: Английский

Citations

6
I2-DMSO-Mediated Construction of 2,3- and 2,4-Disubstituted Pyrimido[1,2-b]indazole Skeletons DOI
Linlin Ma, You Zhou,

Yong‐Xing Tang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 3941 - 3953

Published: Feb. 29, 2024

An efficient synthetic method for constructing 2,3- and 2,4-disubstituted pyrimidio[1,2-b]indazole skeletons through I2-DMSO-mediated substrate-controlled regioselective [4 + 2] cyclization is reported. The reaction conditions are mild, its operation simple, the substrate scope wide. More than 60 derivatives have been synthesized, providing a new methodology related molecules potentially enriching bioactive-molecule libraries.

Language: Английский

Citations

6
Catalyst-Free Cascade Annulation of Enaminones and Aryl Diazonium Tetrafluoroboronates for Cinnoline Synthesis and the Anti-Inflammatory Activity Study DOI

Shanghui Tian,

Yunyun Liu, Changfeng Wan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(4), P. 2433 - 2442

Published: Feb. 8, 2023

A simple and concise method for the synthesis of cinnolines has been developed by reactions readily available enaminones aryl diazonium tetrafluoroboronates. The run efficiently to provide with broad diversity in substructure heating dimethyl sulfoxide without using any catalyst or additive. In addition, primary investigation anti-inflammatory activity these products leads observation p-chlorobenzoyl (3f) p-nitrobenzoyl (3j) as attractive compounds vitro.

Language: Английский

Citations

13
Construction of Pyrazolo[1,5-a]pyrimidines and Pyrimido[1,2-b]indazoles with Calcium Carbide as an Alkyne Source DOI

Xinjie You,

Botao Wang, Fei Wen

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(28), P. 5822 - 5826

Published: Jan. 1, 2024

One-step construction of both 5-arylpyrazolo[1,5- a ]pyrimidines and 2-arylpyrimido[1,2- b ]indazoles using inexpensive, abundant easy-to-handle calcium carbide as solid alkyne source is depicted.

Language: Английский

Citations

5