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

Iodine-Promoted Thioylation and Dicarbonylation of Enaminone α-C Sites: Synthesis of Fully Substituted Thiazoles via C═C Bond Cleavage DOI
Peng Zhao, You Zhou, Can Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2505 - 2515

Published: Feb. 5, 2024

A novel iodine-promoted difunctionalization of α-C sites in enaminones was demonstrated as a means synthesizing variety fully substituted thiazoles by constructing C–C(CO), C–S, and C–N bonds. This transformation allows the realization unusual aryl C2 synthons simultaneously thioylation dicarbonylation sites. preliminary mechanistic study performed indicated that cleavage C═C bonds involves bicyclization/ring-opening oxidative coupling sequence.

Language: Английский

Citations

15

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

Silver‐catalyzed Cascade Bis‐heteroannulation Reaction of Enynones and o‐Hydroxyphenyl Enaminones: Access to Highly Functionalized 3‐Furylmethyl Chromones DOI

Mingshuai Zhang,

Meichen Liu,

Yuetong Qiu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2363 - 2369

Published: March 16, 2024

Abstract A synthetic protocol was developed to synthesize highly functionalized 3‐furylmethyl chromones from enynones and o ‐hydroxyphenyl enaminones via silver‐catalyzed cascade bis‐heteroannulation reaction. This strategy features broad substrate scope good functional group tolerance. Furthermore, the chromone skeleton shows potential application value through further gram‐scale synthesis derivatization.

Language: Английский

Citations

13

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

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

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

Oxidative Free-Radical C(sp2)–H Bond Chlorination of Enaminones with LiCl: Access to Highly Functionalized α-Chlorinated Enaminones DOI

Yunhua Xie,

Zhilai Zhang,

Biao Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8521 - 8530

Published: June 3, 2024

An oxidative free-radical C(sp2)–H bond chlorination strategy of enaminones has been developed by using LiCl as a chlorinating reagent and K2S2O8 an oxidant. This transformation provides new straightforward synthetic methodology to afford highly functionalized α-chlorinated with Z-configuration in good excellent yields.

Language: Английский

Citations

6

Transition-Metal-Free C–H Trifluoromethylthiolation of N,N-Disubstituted Enaminones To Access CF3S-Functionalized Enaminones and Their Application in the Synthesis of CF3S-Heteroaryls DOI

Jinbiao Ying,

Tao Zhou, Yunyun Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 9078 - 9085

Published: June 3, 2024

The α-C–H trifluoromethylthiolation of N,N-disubstituted enaminones has been achieved with simple and cheap CF3SO2Na as the CF3S source. reactions were run at mild temperature (0 °C to rt) using POCl3 only reducing reagent. work represents first example on synthesis α-trifluoromethylthio via direct C–H functionalization. In addition, resulting CF3S-functionalized have proven useful building blocks in various heteroaromatic compounds by annulation reactions.

Language: Английский

Citations

6

Rhodium(III)-Catalyzed Coupling of Quinolin-8-carboxaldehydes with CF3–Imidoyl Sulfoxonium Ylides by Chelation-Assisted C(sp2)-H Bond Activation for the Synthesis of Trifluoromethyl-Substituted Enaminones DOI

Pinyi Li,

Zuguang Yang,

Zhengkai Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10736 - 10747

Published: July 18, 2024

A rhodium(III)-catalyzed aldehydic C(sp

Language: Английский

Citations

6

Photocatalytic Annulation of Enaminones with Thioureas for the Synthesis of 2-Aminothiazoles via Tandem C–S and C–N Bond Formation DOI
Changfeng Wan, Jie‐Ping Wan,

Qihui Huang

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(16), P. 2565 - 2571

Published: April 26, 2024

Abstract Visible-light photocatalytic reactions between enaminones and thioureas leading to thiazole products have been achieved. The annulation process consists of tandem C–S C–N bond formation by running under air atmosphere at ambient temperature. Broad substrate tolerance the sustainable protocol has verified practical synthesis divergent thiazoles with both monocyclic fused cyclic structures.

Language: Английский

Citations

5