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

Shujun Cao,

Weidong Yuan,

Yun Li

и другие.

Chemical Communications, Год журнала: 2022, Номер 58(51), С. 7200 - 7203

Опубликована: Янв. 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.

Язык: Английский

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

Tong Tian,

Guo‐Jun Deng

и другие.

Chinese Chemical Letters, Год журнала: 2022, Номер 34(1), С. 107565 - 107565

Опубликована: Май 28, 2022

Язык: Английский

Процитировано

30

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

и другие.

Organic Letters, Год журнала: 2023, Номер 25(5), С. 838 - 842

Опубликована: Янв. 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.

Язык: Английский

Процитировано

19

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

и другие.

Organic Letters, Год журнала: 2022, Номер 24(21), С. 3828 - 3833

Опубликована: Май 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.

Язык: Английский

Процитировано

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

и другие.

Organic Letters, Год журнала: 2022, Номер 24(28), С. 5137 - 5142

Опубликована: Июль 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.

Язык: Английский

Процитировано

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

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(5), С. 2797 - 2808

Опубликована: Янв. 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.

Язык: Английский

Процитировано

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

и другие.

Organic Letters, Год журнала: 2024, Номер 26(20), С. 4229 - 4234

Опубликована: Май 13, 2024

A copper-catalyzed [3 + 2] annulation of

Язык: Английский

Процитировано

4

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

и другие.

Organic Process Research & Development, Год журнала: 2020, Номер 24(6), С. 909 - 915

Опубликована: Май 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.

Язык: Английский

Процитировано

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

и другие.

Organic Letters, Год журнала: 2021, Номер 23(22), С. 9000 - 9005

Опубликована: Ноя. 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.

Язык: Английский

Процитировано

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

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(9), С. 5804 - 5816

Опубликована: Апрель 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.

Язык: Английский

Процитировано

16

Benzoquinone Ligand-Enabled Ruthenium-Catalyzed Deaminative Coupling of 2-Aminoaryl Aldehydes and Ketones with Branched Amines for Regioselective Synthesis of Quinoline Derivatives DOI

Krishna Prasad Gnyawali,

Aldiyar Shakenov,

Pandula T. Kirinde Arachchige

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(16), С. 11119 - 11135

Опубликована: Июль 26, 2024

The catalytic system generated in situ from the cationic Ru–H complex [(C6H6)(PCy3)(CO)RuH]+BF4– (1) with 2,3,4,5-tetrachloro-1,2-benzoquinone (L1) was found to be highly effective for promoting deaminative coupling reaction of 2-aminoaryl aldehydes branched amines form 2-substituted quinoline products. analogous ketones led regioselective formation 2,4-disubstituted A number biologically active derivatives including graveolinine and a triplex DNA intercalator have been synthesized by using method.

Язык: Английский

Процитировано

3