Lewis Base Catalyzed C−S Bond Formation Through Methyl C(sp3)‐H Thiocyanation of Indoles DOI

Qumruddeen,

Dileep Kumar,

Jobsy Jose

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 13(3)

Published: Dec. 16, 2023

Abstract A Lewis base catalyzed C−S bond formation through thiocyanation of methyl C(sp 3 )−H is reported. The method involves a sequential chlorination and reaction. This simple yet effective protocol works with diverse array indoles to furnish thiocyanated products in good yield (up 85 %). developed also applied for the synthesis phercaptoline (hypotensive agent) umifenovir (antiviral drug).

Language: Английский

Recent advances in visible light-mediated chemical transformations of enaminones DOI
Yu Han,

Liyun Zhou,

Chengyu Wang

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 108977 - 108977

Published: Aug. 26, 2023

Language: Английский

Citations

64

Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation DOI
Jianchao Liu, Jie‐Ping Wan, Yunyun Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(2), P. 597 - 630

Published: Nov. 23, 2023

This review highlights the recent progress in electrochemical difunctionalization of alkenes and alkynes involving C–S/Se bond formation to access organochalcogen frameworks.

Language: Английский

Citations

31

Three-Component Fusion to Pyrazolo[5,1-a]isoquinolines via Rh-Catalyzed Multiple Order Transformation of Enaminones DOI

Demao Chen,

Changfeng Wan, Yunyun Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4833 - 4838

Published: March 22, 2023

A facile and practical method for the synthesis of fused tricyclic pyrazolo[5,1-a]isoquinolines has been realized via reactions enaminones, hydrazine hydrochloride, internal alkynes. By means Rh catalysis, extraordinary high-order bond functionalization, including transformation aryl C–H, ketone C═O, alkenyl C–N bonds in marks major feature cascade reactions. The results disclose individual advantage enaminones design novel efficient synthetic methods.

Language: Английский

Citations

24

Electrochemical Enaminone-Thioamide Annulation and Thioamide Dimeric Annulation for the Tunable Synthesis of Thiazoles and 1,2,4-Thiadiazole DOI

Qihui Huang,

Jianchao Liu, Jie‐Ping Wan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(25), P. 5263 - 5268

Published: June 14, 2024

A green and sustainable electrochemical oxidative cyclization of enaminones with thioamides under metal- oxidant-free conditions has been developed, providing an efficient approach for thiazole synthesis. Furthermore, 1,2,4-thiadiazoles can be selectively accessed via the dimerization in absence enaminones.

Language: Английский

Citations

18

An electrochemical-enabled cascaded cyclization of enaminones with potassium thiocyanate and alcohols to access 2-alkoxythiazoles DOI
Dandan Li, Long Chen,

Yang Jin

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(12), P. 4656 - 4661

Published: Jan. 1, 2023

An electrochemical-enabled three-component cascaded cyclization of enaminones with potassium thiocyanate and alcohols to access 2-alkoxythiazoles has been developed under external oxidant-free conditions.

Language: Английский

Citations

22

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

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

I2‐Promoted [3+2] Cyclization of Thiocarbamates with Enaminones: a Protocol for the Synthesis of Polysubstituted Thiazol‐2(3H)‐ones DOI

Xiao‐Hu Xu,

Jia‐Hao Weng,

Yi Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(7), P. 1649 - 1653

Published: Feb. 7, 2024

Abstract An I 2 ‐promoted [3+2] cyclization reaction between thiocarbamates with enaminones has been developed for the synthesis of thiazol‐2(3 H )‐one derivatives. This protocol involves C−S and C−N bond formation exhibits good functional group tolerance. The proceeded well at room temperature provided up to 98% yield desired products.

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

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