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

One-Pot Synthesis of 2-Acetyl-1H-pyrroles from N-Propargylic β-Enaminones via Intermediacy of 1,4-Oxazepines DOI

Nilay Kanova,

Buse Aysen Dundar,

Yilmaz Kelgokmen

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(9), P. 6289 - 6304

Published: April 19, 2021

A one-pot two-step protocol for the synthesis of 2-acetyl-1H-pyrroles from N-propargylic β-enaminones was described. When treated with zinc chloride in refluxing chloroform, produced situ 2-methylene-2,3-dihydro-1,4-oxazepines, which, upon further methanol chloride, afforded 2-acetyl-1H-pyrroles. The process found to be general a wide variety and yielded diverse range good high yields large substrate scope functional group tolerance. This operationally easy method may provide rapid access functionalized pharmacological interest.

Language: Английский

Citations

21

Base‐Promoted Michael Addition/Smiles Rearrangement/ N‐Arylation Cascade: One‐Step Synthesis of 1,2,3‐Trisubstituted 4‐Quinolones from Ynones and Sulfonamides DOI
Jing Liu,

Dan Ba,

Weiwei Lv

et al.

Advanced Synthesis & Catalysis, Journal Year: 2019, Volume and Issue: 362(1), P. 213 - 223

Published: Nov. 12, 2019

Abstract A general, practical, and environmentally friendly protocol to synthesize 1,2,3‐trisubstituted 4‐quinolones from readily available ynones sulfonamides was developed. The construction of one C−C bond two C−N bonds via cleavage N−S, C−S, C−X (X=F, Cl, Br, O) is achieved under transition‐metal‐free conditions in step. This transformation generates 1 equiv. sulfur dioxide hydrogen halide as the byproducts. broad substrate scope functional group tolerance are demonstrated by 52 examples 4‐quinolones. preliminary mechanistic study supports a sequential Michael addition/Smiles rearrangement/ N ‐arylation reaction pathway. magnified image

Language: Английский

Citations

24

Rhodium(II)-catalyzed multicomponent assembly of α,α,α-trisubstituted esters via formal insertion of O–C(sp3)–C(sp2) into C–C bonds DOI

Dan Ba,

Si Wen,

Qingyu Tian

et al.

Nature Communications, Journal Year: 2020, Volume and Issue: 11(1)

Published: Aug. 24, 2020

Language: Английский

Citations

22

Regioselective Synthesis of 2,4-Diaryl-6-trifluoromethylated Pyridines through Copper-Catalyzed Cyclization of CF3-Ynones and Vinyl Azides DOI
Jixin Wang,

Dang Xuan Ba,

Mengqi Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(9), P. 6423 - 6432

Published: April 27, 2021

A novel copper-catalyzed cyclization of readily available vinyl azides with CF3-ynones is steadily achieved under mild conditions to furnish the versatile 2,4-diaryl-6-trifluoromethylated pyridine products, which are great interest in medicinal chemistry. The generation iminophosphorane intermediates from through Staudinger-Meyer reaction ensures subsequent 1,4-addition process this transformation.

Language: Английский

Citations

18

Base-promoted C–C bond cleavage for the synthesis of 2,3,4-trisubstituted pyrroles from N-propargyl β-enaminones DOI

Bailu Ge,

Weiwei Lv,

Jia Yu

et al.

Organic Chemistry Frontiers, Journal Year: 2018, Volume and Issue: 5(21), P. 3103 - 3107

Published: Jan. 1, 2018

The synthesis of 2,3,4-trisubstituted pyrroles via base-promoted C–C bond cleavage reaction N-propargyl β-enaminones is reported.

Language: Английский

Citations

22

A Reusable CNT‐Supported Single‐Atom Iron Catalyst for the Highly Efficient Synthesis of C−N Bonds DOI
Qifeng Ding, Yang Yu, Fei Huang

et al.

Chemistry - A European Journal, Journal Year: 2020, Volume and Issue: 26(20), P. 4592 - 4598

Published: Feb. 13, 2020

C-N bond formation is regarded as a very useful and fundamental reaction for the synthesis of nitrogen-containing molecules in both organic pharmaceutical chemistry. Noble-metal homogeneous catalysts have frequently been used formation, however, these number disadvantages, such high cost, toxicity, low atom economy. In this work, low-toxic cheap iron complex (iron ethylene-1,2-diamine) has loaded onto carbon nanotubes (CNTs) to prepare heterogeneous single-atom catalyst (SAC) named Fe-Nx /CNTs. We employed SAC bonds first time. It was found that /CNTs an efficient starting from aromatic amines ketones. Its catalytic performance excellent, giving yields up 96 %, six-fold higher than obtained with noble-metal catalysts, AuCl3 RhCl3 The showed efficacy reactions thirteen amine substrates, without need additives, seventeen enaminones were obtained. High-angle annular dark-field scanning transmission electron microscopy combination X-ray absorption spectroscopy revealed species well dispersed single atoms might be active species. This potential industrial applications it could cycled seven times any significant loss activity.

Language: Английский

Citations

20

Divergent Synthesis of Unsymmetrical Bis-heteroaryl Ketones via Base-Promoted Cascade Reactions of 1,2-Alkynedione-Derived N-Propargylic β-Enaminones DOI
Debojyoti Bag,

Sheetal Saini,

Mahesh S. Rathod

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11665 - 11670

Published: Aug. 6, 2024

Herein we disclose a transition-metal-free, one-pot two-step strategy for the synthesis of unsymmetrical bis-heteroaryl ketones.

Language: Английский

Citations

2

Tandem site-selective bromination and highly regioselective Heck reaction of N-allyl enaminones: chemodivergent synthesis of polysubstituted pyrroles and pyridines DOI
Xiyan Duan, Junqi Wang, Huijun Li

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5532 - 5537

Published: Jan. 1, 2024

Chemodivergent synthesis of polysubstituted pyrroles and pyridines from N -allyl enaminones via tandem site-selective bromination the highly regioselective Heck reaction.

Language: Английский

Citations

2

PIDA-mediated intramolecular oxidative C–N bond formation for the direct synthesis of quinoxalines from enaminones DOI Creative Commons
Hong Zhang, Jinhai Shen, Zhenhui Yang

et al.

RSC Advances, Journal Year: 2019, Volume and Issue: 9(14), P. 7718 - 7722

Published: Jan. 1, 2019

A intramolecular oxidative C(sp2)-N bond formation mediated by hypervalent iodine(iii) to obtain quinoxalines from readily available N-(2-acetaminophenyl)enaminones was developed. tandem process involving PIDA-mediated condensation cyclization and a subsequent elimination postulated, which highly efficient metal-free under mild conditions. Moreover, flexible structural modifications of bearing carbonyl groups are interest for further transformations as building blocks in organic synthesis.

Language: Английский

Citations

18

Recent Advances for the Synthesis of N‐Unsubstituted Pyrroles DOI
Ilya V. Efimov, Л. Н. Куликова, Almira R. Miftyakhova

et al.

ChemistrySelect, Journal Year: 2021, Volume and Issue: 6(48), P. 13740 - 13772

Published: Dec. 22, 2021

Abstract Pyrroles are an interesting class of heterocyclic compounds due to their widespread use both in medical chemistry and the new materials. Search development effective methods for synthesis pyrrole ring is urgent task. Along with this, systematization already known equally important Herein, we focused on results NH‐pyrroles that have been obtained since 2015.

Language: Английский

Citations

12