Synthesis and structure of dialkyl (Z)-3-amino-2-cyano-4-diazopent-2-enedioates DOI
Issa Yavari,

Ramin Mohsenzadeh,

Jasmine Kayanian

et al.

Monatshefte für Chemie - Chemical Monthly, Journal Year: 2020, Volume and Issue: 151(12), P. 1829 - 1834

Published: Nov. 22, 2020

Language: Английский

Recent Advances in Reactions Using Enaminone in Water or Aqueous Medium DOI

Zhouying Wang,

Baoli Zhao,

Yunyun Liu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(9), P. 1508 - 1521

Published: April 8, 2022

Abstract Enaminones have in the past decade received renewed interest organic synthesis by acting as highly versatile building blocks. Particularly, featured amino and carbonyl group enaminone structure endow them with ability of tolerating water via hydrogen bonding effect. Thus, designing synthetic methods aqueous medium enaminones main blocks has extensive attention notable success. Based on our longstanding efforts interests chemistry, we review herein research advances participated medium. magnified image

Language: Английский

Citations

83
Rongalite as C1 Synthon in the Synthesis of Divergent Pyridines and Quinolines DOI
Huan Gao,

Liyun Zhou,

Jie‐Ping Wan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7188 - 7198

Published: May 12, 2023

Rongalite has been used as a cheap and efficient carbon synthon for the synthesis of divergent N-heteroaromatics, including different pyridines quinolines. The selective products can be achieved by employing enaminones or enaminones/anilines reaction partners. In addition, compared with using conventional aldehyde synthons, rongalite displays an evident advantage in providing considerably higher product yields under milder conditions. GC-MS analysis process performed to probe possible mechanism.

Language: Английский

Citations

32
Amine-catalyzed synthesis of N2-sulfonyl 1,2,3-triazole in water and the tunable N2-H 1,2,3-triazole synthesis in DMSO via metal-free enamine annulation DOI
Y. P. Guo, Yunyun Liu, Jie‐Ping Wan

et al.

Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 33(2), P. 855 - 858

Published: Aug. 8, 2021

Language: Английский

Citations

48
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

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(19), P. 13195 - 13203

Published: Sept. 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.

Language: Английский

Citations

30
Photocatalytic Pyridine Synthesis with Enaminones and TMEDA under Metal-Free Conditions DOI

Junlong Zeng,

Tao Zhou, Jianchao Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 11060 - 11066

Published: July 24, 2024

Reported herein is a new photocatalytic annulation for the synthesis of 2,3,4,6-tetrasubstituted pyridines with enaminones and N,N,N′,N′-tetramethyl ethylenediamine (TMEDA). The reactions take place without requiring transition metal reagent provide products broad scope. methyl in TMEDA acts as carbon source pyridine ring construction, BrCF2CO2Et plays role terminal oxidant free radical quenching.

Language: Английский

Citations

7
Scissoring Enaminone C═C Double Bond by Free Radical Process for the Synthesis of α-Trifluoromethyl Ketones with CF3SO2Na DOI
Lu Gan, Qing Yu, Yunyun Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 86(1), P. 1231 - 1237

Published: Dec. 8, 2020

The C═C double bond cleavage on tertiary enaminones, enabling the formation of a new C–CF3 bond, has been realized as practical method for synthesis α-trifluoromethyl ketones with only promotion TBHP and ambient heating. Control experiments support that reactions proceed via featured free radical process. deuterium labeling experiment employing D2O indicates water participated in product by donating hydrogen atom newly generated α-C–H product.

Language: Английский

Citations

36
Acid-Catalyzed, Metal- and Oxidant-Free C=C Bond Cleavage of Enaminones: One-Pot Synthesis of 3,4-Dihydroquinazolines DOI Creative Commons
Ting Chen, Ting Huang,

Mao-Chun Ye

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(2), P. 350 - 350

Published: Jan. 16, 2025

In this study, we present the HOAc-catalyzed selective cleavage of C=C double bond enaminones, enabling formation a new C–N and C=N for one-pot synthesis 2-substituted 3,4-dihydroquinazolines directly from ynones 2-(aminomethyl)anilines. This method operates in ethanol under transition-metal-free oxidant-free conditions, offering sustainable efficient approach with broad functional group tolerance.

Language: Английский

Citations

0
Metal-Free Synthesis of 1,2,3-Triazoles in Pure Water via the Enamine Modified Annulation Reactions with Tosyl Azide DOI Open Access
Xixi Zheng, Yunyun Liu, Jie‐Ping Wan

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 41(7), P. 2700 - 2700

Published: Jan. 1, 2021

The synthesis of full substituted 1,2,3-triazoles has been accomplished with high efficiency through the reactions readily available β-substituted NH-enaminoesters and tosyl azide Et3N catalysis.In this method, water was used as sole medium for which provide 1,2,3-triazole products broad scope moderate to excellent yield.Control experiments disclose that employment stable NH-enamines substrates is key factor enabling mediated probably via hydrogen bonding effect between NH group water.In addition, novel selective production N-alkyl sulfonamides corresponding enaminoesters observed under identical conditions.

Language: Английский

Citations

16
Advanced Guareschi–Thorpe synthesis of pyridines in green buffer, and pH-controlled aqueous medium with ammonium carbonate DOI Creative Commons
Fatemeh Tamaddon,

Sajedeh Maddah-Roodan

RSC Advances, Journal Year: 2023, Volume and Issue: 13(35), P. 24846 - 24853

Published: Jan. 1, 2023

Hydroxy-cyanopyridines are easily synthesized via an advanced version of the Guareschi–Thorpe reaction by three-component condensation alkyl cyanoacetate or cyanoacetamide with 1,3-dicarbonyls and ammonium carbonate in aqueous medium.

Language: Английский

Citations

5
Synthesis of α‐Hydroxyl Ketones by Metal‐Free C=C Double Bond Cleavage of Enaminones in Aqueous Medium DOI
Lu Gan, Yunyun Liu, Chaoli Wang

et al.

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(31)

Published: Aug. 16, 2023

Abstract The C=C double bond cleavage of enaminones has been accomplished in the presence methyl sulfonyl azide (MSA) to provide α‐hydroxyl ketones via reaction with water. major process reactions consists formation a key α‐diazoketone intermediate resulting from enaminone‐azide annulation, and successive decomposition. Totally 22 have synthesized yield range 43 %–83 %.

Language: Английский

Citations

4