Photoredox/copper cocatalyzed domino cyclization of oxime esters with TMSCN: access to antifungal active tetrasubstituted pyrazines DOI

Shujun Cao,

Weidong Yuan,

Yun Li

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(51), P. 7200 - 7203

Published: Jan. 1, 2022

A photoredox/copper cocatalyzed domino cyclization of oxime esters with TMSCN has been developed. range structurally novel tetrasubstituted pyrazines have obtained. This method features high bond-forming efficiency, step economy, broad substrate scope, and gram-scale synthesis. Moreover, preliminary bioactivity evaluation pyrazine products shows their promising antifungal activities.

Language: Английский

Diverse catalytic systems for nitrogen-heterocycle formation from O-acyl ketoximes DOI Open Access
Zhonghua Qu,

Tong Tian,

Guo‐Jun Deng

et al.

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 34(1), P. 107565 - 107565

Published: May 28, 2022

Language: Английский

Citations

31

Copper-Catalyzed Annulation of O-Acyl Oximes with Cyclic 1,3-Diones for the Synthesis of 7,8-Dihydroindolizin-5(6H)-ones and Cyclohexanone-Fused Furans DOI
Hai‐Tao Yang,

Su-Qing Zhou,

Danmei Chen

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(5), P. 838 - 842

Published: Jan. 27, 2023

A copper-catalyzed annulation of O-acyl oximes with cyclic 1,3-diones has been developed for the concise synthesis 7,8-dihydroindolizin-5(6H)-ones and cyclohexanone-fused furans through substituent-controlled selective radical coupling process. 2-Alkyl undergo C-C coupling, while 2-unsubstituted C-O coupling.

Language: Английский

Citations

20

Synthesis of Stable N–H Imines with a Benzo[7,8]indolizine Core and Benzo[7,8]indolizino[1,2-c]quinolines via Copper-Catalyzed Annulation of α,β-Unsaturated O-Acyl Ketoximes with Isoquinolinium N-Ylides DOI
Chun‐Bao Miao,

Xiao-Qi Qiang,

Xiaoli Xu

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(21), P. 3828 - 3833

Published: May 23, 2022

A copper-catalyzed annulation of α,β-unsaturated O-acyl ketoximes with isoquinolinium N-ylides has been developed for the concise synthesis stable N-H imines a benzo[7,8]indolizine core. When β-(2-bromoaryl)-α,β-unsaturated are used as starting materials, cascade cyclization occurs to afford benzo[7,8]indolizino[1,2-c]quinolines.

Language: Английский

Citations

22

Access to 3-Amino-[1,2,4]-triazolo Pyridines and Related Heterocycles via Electrochemically Induced Desulfurative Cyclization DOI
Yunfei Hu, Li Chen,

Canlin Zou

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(28), P. 5137 - 5142

Published: July 8, 2022

An efficient, one-pot approach has been established for synthesizing a wide range of 3-amino-[1,2,4]-triazolo pyridines and related heterocycles from the electrochemically induced desulfurative cyclization 2-hydrazinopyridines with isothiocyanates. The protocol allows formation C–N bonds under simple conditions without transition metals or external oxidants. practicability this strategy is demonstrated by its broad substrate scope, good functional group compatibility, gram-scale synthesis. late-stage modification enables us to obtain several molecules potent anticancer activity.

Language: Английский

Citations

19

[3+1+1+1] Annulation to the Pyridine Structure in Quinoline Molecules Based on DMSO as a Nonadjacent Dual-Methine Synthon: Simple Synthesis of 3-Arylquinolines from Arylaldehydes, Arylamines, and DMSO DOI
Tonglin Yang,

Hui Li,

Zhiwen Nie

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(5), P. 2797 - 2808

Published: Jan. 25, 2022

A [3+1+1+1] annulation of arylamines, arylaldehydes, and dimethyl sulfoxide (DMSO) to the pyridine structure in quinolines using DMSO as a nonadjacent dual-methine (═CH-) synthon is disclosed. In this annulation, arylamines provide two carbon atoms one nitrogen atom, arylaldehydes furnish provides methines ring quinoline molecules. This simple approach for synthesis 3-arylquinolines from readily available substrates useful yields. On basis control experiments literature, plausible mechanism proposed.

Language: Английский

Citations

18

Copper-Catalyzed [3 + 2] Annulation of O-Acyl Oximes with 4-Sulfonamidophenols for the Synthesis of 5-Sulfonamidoindoles and 2-Amido-5-sulfonamidobenzofuran-3(2H)-ones DOI

Zi-Jun Hu,

Wei Chen,

Xinyu Lyu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4229 - 4234

Published: May 13, 2024

A copper-catalyzed [3 + 2] annulation of

Language: Английский

Citations

4

Recent Advances in Nonprecious Metal Catalysis DOI
Robert A. Singer, Sébastien Monfette, David J. Bernhardson

et al.

Organic Process Research & Development, Journal Year: 2020, Volume and Issue: 24(6), P. 909 - 915

Published: May 14, 2020

Nonprecious metal catalysis is a highly active area of research for both industrial and academic laboratories. New methods that efficiently generate useful functionality in cost-effective, high yielding, environmentally friendly ways naturally garner attention from process chemists many different industries. This series highlights summarizes literature on the general topic nonprecious over four-month timeframes will focus major trends field are interest pharmaceutical industry. The first installment selected transformations using copper, nickel, iron catalysts.

Language: Английский

Citations

25

Iodine-imine Synergistic Promoted Povarov-Type Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and Their Application to a Copper/Ligand Catalytic System DOI

Qi-Qi Hu,

Yanting Gao, Jiachen Sun

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(22), P. 9000 - 9005

Published: Nov. 8, 2021

An efficient iodine-imine synergistic promoted Povarov-type multicomponent reaction was reported for the synthesis of a practical 2,2′-biquinoline scaffold. The tandem annulation has reconciled iodination, Kornblum oxidation, and Povarov aromatization, where methyl group azaarenes represents uniquely reactive input in reaction. This method broad substrate scope mild conditions. Furthermore, these derivatives had been directly used as bidentate ligands metal-catalyzed reactions.

Language: Английский

Citations

21

Access to 4-Trifluoromethyl Quinolines via Cu-Catalyzed Annulation Reaction of Ketone Oxime Acetates with ortho-Trifluoroacetyl Anilines under Redox-Neutral Conditions DOI
Zhen‐Hua Wang,

Li‐Wen Shen,

Ping Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(9), P. 5804 - 5816

Published: April 27, 2022

An efficient Cu-catalyzed annulation reaction of ketone oxime acetates with ortho-trifluoroacetyl anilines has been disclosed. With the developed protocol, a series 4-trifluoromethyl quinolines were obtained in good to excellent yields (58-99%) under redox-neutral conditions. The protocol also could be extended ferrocene-based for construction ferrocene-substituted fluorine-containing quinolines.

Language: Английский

Citations

16

Copper-Catalyzed Annulation of α,β-Unsaturated Ketoximes with Dialkyl Acetylenedicarboxylates for the Synthesis of Highly Substituted Pyridines DOI

Shi-Mei He,

Yunbo Yang,

Lv-Yan Liu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 24, 2025

A copper-catalyzed [4 + 2] annulation protocol from readily available α,β-unsaturated ketoximes and dialkyl acetylenedicarboxylates has been achieved. The approach enables the expedient construction of a series structurally new highly substituted pyridines with good functional group tolerance.

Language: Английский

Citations

0