Organic Base-Promoted C–N- and C–O-Coupled Domino Cyclization Strategy: Syntheses of Oxazine-6-ones and 4-Pyrimidinols DOI
Anindya S. Manna, Rajesh Nandi, Tanmoy Kumar Ghosh

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5650 - 5664

Published: April 5, 2024

Oxazine-6-one and 4-pyrimidinol are two important frameworks in pharmaceutical production. Herein, we disclosed a simple, efficient, inexpensive organic base-promoted additive-stimulated protocol for the syntheses of variably functionalized oxazine-6-ones 4-pyrimidinols employing acetonitrile solvent under conventional heating conditions using an oil bath through C–N C–O coupled domino steps. This simple practicable productive utilizes easily producible cheap precursors, namely, benzimidates or benzamidines, with differently substituted dicyano-olefins, it comprises step economy, robustness, moisture insensitive affording high yield that avoids use transition-metal catalysts, multistep multicomponent strategy, harsh reaction involving hazardous chemicals. method is scalable into gram-scale production good yield.

Language: Английский

Resurgence and advancement of photochemical hydrogen atom transfer processes in selective alkane functionalizations DOI Creative Commons
Liang Chang, Shun Wang, Qing An

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(25), P. 6841 - 6859

Published: Jan. 1, 2023

The selective functionalization of alkanes has long been recognized as a prominent challenge and an arduous task in organic synthesis. Hydrogen atom transfer (HAT) processes enable the direct generation reactive alkyl radicals from feedstock have successfully employed industrial applications such methane chlorination process,

Language: Английский

Citations

67

“Alkene-to-Alkene” Difunctionalization of Enaminones for the Synthesis of Polyfunctionalized Alkenes by Transition-Metal-Free C–H and C–N Bond Transformation DOI

J. Ye,

Yunyun Liu,

Jin Luo

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(47), P. 8451 - 8456

Published: Nov. 16, 2023

The three-component reactions of enaminones, disulfides, and alcohols for the synthesis polyfunctionalized alkenes have been realized via C-H C-N bond transformation on enaminones. proceed in a novel "alkene-to-alkene" difunctionalization mode without using any transition metal. application alkene products divergent sulfenyl heteroaryls, including sulfenylated pyrazoles, pyrimidines, isoxazoles, simple annulation has also verified.

Language: Английский

Citations

29

Development and Application of Trifluoromethoxylating Reagents DOI
Ya‐Feng Si,

Pingping Tang

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(17), P. 2179 - 2196

Published: April 25, 2023

Comprehensive Summary The trifluoromethoxy functional group has received increasing attention in recent years due to its distinctive properties such as good metabolic stability, appropriate lipophilicity and special electrical properties. Thus, the development of new reagents strategies direct trifluoromethoxylation are attracting enthusiasm many fluorine chemical workers. At present, nucleophilic radical trifluoromethoxylating have made major breakthroughs, greatly promoting chemistry. This review is mainly divided into two parts: types, focusing on history, characteristics applications various reagents.

Language: Английский

Citations

25

Recent Advances in Electrochemical Cascade Cyclization Reactions DOI
Cai Zhang, Yunyun Liu,

Demao Chen

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2911 - 2925

Published: Feb. 20, 2023

Abstract This review highlights recent progress in electrochemical cascade cyclization reactions for the synthesis of carbon rings and heterocycles, such as pyridines, quinolines, phenanthridines, cinnolines, 1,4-dihydroquinolines, oxindoles, imidazo[1,5-α]pyridines, imidazoles, etc. The works included herein are introduced two major sections heterocycle construction carbocycle reactions, covering reported from 2012 to 2022. 1 Introduction 2 Electrochemical Cascade Cyclization Synthesis Heterocycles 2.1 Pyridines, Quinolines, Phenanthridines, Cinnolines 2.2 1,4-Dihydroquinolines, Hexacyclic Sulfonamides, Thiazines 2.3 Hydroisoquinolinones Hydroquinolinones 2.4 Quinazolin-4(3H)-ones 2.5 4H-3,1-Benzoxazines 2.6 Oxindoles 2.7 Indolines Indoles 2.8 Imidazo[1,5-α]pyridines Imidazoles 2.9 Imidazolones, Imidazolidinones, Oxazolones, Oxazolidinones 2.10 Benzoxazoles, Oxazolines, Isoxazolines 2.11 Furans Dihydrofurans 2.12 Indolizines, Pyrazoles, Triazolium Inner Salts 2.13 Sulfonated Benzothiophenes, Thiazoles, Dihydrothiazoles, 1,3,4-Thiadiazoles 2.14 Lactones 3 Construction Carbocycles 3.1 Carbon Polycycles Spiroindenes 3.2 Difluoroacyl (Hetero)arenes Indenones 4 Conclusion

Language: Английский

Citations

23

Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C-H functionalization and chromone annulation of enaminones DOI
Tao Zhou, Jing Zhou, Yunyun Liu

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(11), P. 109683 - 109683

Published: March 2, 2024

Language: Английский

Citations

15

Metal‐Free Electrochemical Trifluoromethylation of Imidazole‐Fused Heterocycles with Trifluoromethyl Thianthrenium Triflate DOI
Chang Ge,

Lipeng Qiao,

Yuyang Zhang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(15), P. 1679 - 1685

Published: March 15, 2024

Comprehensive Summary A novel and eco‐friendly electrochemical activation of trifluoromethyl thianthrenium triflate (TT–CF 3 + OTf − ) for trifluoromethylation imidazole‐fused heteroaromatic compounds was established. This method involves the direct electrolysis TT–CF without requirement external oxidants or catalysts, aligning with principles green chemistry. wide range including imidazo[1,2‐ a ]pyridines benzo[ d ]imidazo[2,1‐ b ]thiazoles have been successfully trifluoromethylated using this technique, exhibiting excellent compatibility various functional groups broad substrate scope. Moreover, method's applicability one‐pot sequential reactions enables reduction waste resource consumption by eliminating need intermediate purification steps.

Language: Английский

Citations

9

Annulation of enaminones with quinonediimides/quinoneimides for selective synthesis of indoles and 2-aminobenzofurans DOI

Zukang Zhong,

Lihua Liao, Yunyun Liu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(45), P. 6885 - 6888

Published: Jan. 1, 2023

The annulation reactions of enaminones with quinonediimides/quinoneimides for the selective synthesis indoles and 2-aminobenzofurans have been realized. With Zn(II) catalysis, quinonediimides reacted to give via HNMe2-elimination-based aromatization. Fe(III) quinoneimides provided a key dehydrogenative

Language: Английский

Citations

19

Mediator-free electrochemical trifluoromethylation: a cascade approach for the synthesis of trifluoromethylated isoxazolines DOI
Kingshuk Mahanty, Suman Kumar Saha, Atreyee Halder

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(30), P. 4467 - 4470

Published: Jan. 1, 2023

The developed methodology describes an environmentally benign protocol for electro-oxidative CF3-radical generation, followed by cascade cyclization fabricating isoxazoline scaffold from a β,γ-unsaturated oxime. Consecutive C-O and C-C bond formations were achieved through this method featuring mild, robust, scalable reaction conditions broad substrate scope. Mechanistic studies revealed the necessity of anodic oxidation process. Further conversion afforded other valuable derivatives.

Language: Английский

Citations

17

Recent Advances on C—H Functionalization via Oxidative Electrophotocatalysis DOI

Aman Hasil,

Rui Chang,

Juntao Ye

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(3), P. 728 - 728

Published: Jan. 1, 2024

Language: Английский

Citations

8

Chemodivergent Synthesis of Benzofurans and 2,3‐Dihydrobenzofurans via Tandem Oxidative Annulation of Enaminones and Salicylaldehydes DOI
Xiyan Duan, Hui Li, Junqi Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(15), P. 1727 - 1733

Published: March 26, 2024

Comprehensive Summary Chemodivergent synthesis of benzofurans and 2,3‐dihydrobenzofurans has been realized. Under a reaction system consisting DBDMH K 2 CO 3 as promotors, controlled conditions enabled the formation two sets valuable heterocycles from tandem transformation enaminones salicylaldehydes. The key to success was identification parameters, in which imine intermediate formed by transient halogenation coupling substitution processes underwent either aldol condensation/annulation or hydrolysis/aldol condensation. additives NH 4 Cl Fe (SO ) unique selectivity this reaction. A broad substrate scope salicylaldehydes employed reaction, demonstrating excellent functional group tolerance versatility.

Language: Английский

Citations

7