Phosphine ligand-free RuCl3-catalyzed reductive N-alkylation of aryl nitro compounds

Tan, Dali; Li, Hong Xi; Young, David J.; Lang, Jihui

doi:10.1016/j.tet.2016.05.036

Cited by 30 publications

(8 citation statements)

References 58 publications

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“…Yield 3.18 g (99%), white solid, mp 72–73 °C (65–67 °C); IR (KBr) ν max 3419, 1605, 1509, 1250, 753 cm –1 ; 1 H NMR (500 MHz, CDCl 3 ) δ 3.84 (s, 3H, OMe), 4.29 (s, 3H, NCH 2 ), 6.68 (d, J = 7.6 Hz, 2H, H2,6-NPh), 6.76 (dd, J = 7.3, 7.3 Hz, 1H, H4-NPh), 6.92 (d, J = 8.6 Hz, 2H, H3,5-Ar), 7.22 (ddd, J = 7.6, 7.4, 0.9 Hz, 2H, H3,5-NPh), 7.33 (d, J = 8.6 Hz, 2H, H-2,6-Ar). Anal.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel–Crafts Alkylation Strategy

et al. 2018

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The new efficient synthesis of biologically important 3-hydroxy-4-arylquinolin-2-ones through the Darzens condensation (epoxidation) of dichloroacetanilides with aromatic aldehydes followed by one-pot dechlorative epoxide-arene cyclization is described. This methodology has been utilized for the synthesis of naturally occurring viridicatol, a fungal metabolite isolated from the penicillium species.

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Section: Methodsmentioning

confidence: 99%

Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel–Crafts Alkylation Strategy

et al. 2018

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“…All analytical data was in accordance to previously published data. [41][42][43][44][45][46] General Procedure B was added dropwise at −50 °C, stirred for 30 minutes and then warmed to room temperature. The reaction mixture was quenched with a saturated aqueous solution of NH4Cl.…”

Section: Characterizationmentioning

confidence: 99%

“…All analytical data in accordance with previously published data. [41][42][43][44][45][46] (E)-Prop-1-ene-1,3-diylbis(trimethylsilane) (5)…”

Section: N-phenyl Imines 2; General Procedures Amentioning

confidence: 99%

Aza-Peterson Olefinations: Rapid Synthesis of (E)-Alkenes

Britten¹,

Basson²,

Roberts³

et al. 2021

Synthesis

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“…The solid products were easily recrystallized from EtOH. In the case of oil products, EtOH was evaporated under reduced pressure to afford the essentially pure products (62,(81)(82)(83)(84)(85)(86)(87).…”

Section: Typical Procedures For the Synthesis Of Imine 5a-q Catalyzed mentioning

confidence: 99%

MCM-41 mesoporous silica: a highly efficient and recoverable catalyst for rapid synthesis of α-aminonitriles and imines

Eslami

Dekamin

Motlagh

et al. 2018

Green Chemistry Letters and Reviews

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In this work, pure MCM-41 mesoporous silica with active mesoporous sites has been successfully applied, as a highly efficient and recoverable catalyst, for the rapid and convenient synthesis of α-aminonitriles and imines. Various imines, as the intermediate of the Strecker reaction, were simply prepared from condensation of a wide range of aldehydes and amines in the presence of low loading of MCM-41 mesoporous silica under solvent-free conditions at room temperature in high to quantitative yields. Furthermore, the corresponding α-aminonitrile derivatives were prepared through the three-component Strecker reaction using trimethylsilylcyanide catalyzed by MCM-41 as a bifunctional heterogeneous mesoporous solid catalyst.

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Phosphine ligand-free RuCl3-catalyzed reductive N-alkylation of aryl nitro compounds

Cited by 30 publications

References 58 publications

Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel–Crafts Alkylation Strategy

Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel–Crafts Alkylation Strategy

Aza-Peterson Olefinations: Rapid Synthesis of (E)-Alkenes

MCM-41 mesoporous silica: a highly efficient and recoverable catalyst for rapid synthesis of α-aminonitriles and imines

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