Heterogeneous SnCl2/SiO2versus Homogeneous SnCl2Acid Catalysis in the Benzo[N,N]-heterocyclic Condensation

Darabi, Hossein Reza; Aghapoor, Kioumars; Mohsenzadeh, Farshid; Jalali, Mohammad Reza; Talebian, Shiva; Ebadinia, Leila; Khatamifar, Ehsan; Aghaee, Ali

doi:10.5012/bkcs.2011.32.1.213

Cited by 22 publications

(11 citation statements)

References 48 publications

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“… 36 , 41 , 42 Condensation with electron-rich 4,4′-dimethoxybenzil required alternate conditions involving a SnCl 2 /SiO 2 solid support Lewis acid catalyst to give appreciable amounts of 4d (44%). 43 Finally, the TPz D–A–D dyes (TPz–Et, TPz–CO 2 Et, TPz–Ph, TPz–PhOMe, TPz–PhCO 2 Me) were obtained by Pd-catalyzed direct C–H arylation reaction of 4a – 4e in yields ranging from 68%–35% with the use of X-Phos 38 or P t Bu 3 39 as ligand. The palladium-catalyzed C–H activation conditions were optimized with TPz–Et.…”

Section: Resultsmentioning

confidence: 99%

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Donor–Acceptor–Donor Thienopyrazines via Pd-Catalyzed C–H Activation as NIR Fluorescent Materials

et al. 2015

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A series of thienopyrazine-based donor–acceptor–donor (D–A–D) near-infrared (NIR) fluorescent compounds were synthesized through a rapid, palladium-catalyzed C–H activation route. The dyes were studied through computational analysis, electrochemical properties analysis, and characterization of their photophysical properties. Large Stokes shifts of approximately 175 nm were observed, which led to near-infrared emission. Computational evaluation shows that the origin of this large Stokes shift is a significant molecular reorganization particularly about the D–A bond. The series exhibits quantum yields of up to φ = >4%, with emission maxima ranging from 725 to 820 nm. The emission is strong in solution, in thin films, and also in isolation at the single-molecule level. Their stable emission at the single-molecule level makes these compounds good candidates for single-molecule photon sources in the near-infrared.

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Section: Resultsmentioning

confidence: 99%

“…Bis(hexyloxy)triphenylamine bromide was prepared according to literature procedures. 53 Diethyl 2,3-dioxosuccinate, 54 dimethyl 4,4′-oxalyldibenzoate, 55 and the SnCl 2 /SiO 2 solid support catalyst 43 were prepared according to literature procedures. Thin-layer chromatography (TLC) was visualized with UV.…”

Section: Methodsmentioning

confidence: 99%

Donor–Acceptor–Donor Thienopyrazines via Pd-Catalyzed C–H Activation as NIR Fluorescent Materials

et al. 2015

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“…2,3-Disubstituted quinoxalines have also been prepared by Suzuki-Miyaura coupling reaction 35 , condensation of o-phenylenediamines and 1,2-dicarbonyl compounds in MeOH/AcOH under microwave irradiation 36 , iodine catalyzed cyclocondensation of 1,2-dicarbonyl compounds and substituted o-phenylene diamines in DMSO 37 and CH 3 CN 38 . Different catalysts used for quinoxaline synthesis such as IBX 39 , Oxalic Acid 40 , SBSSA 41 , Microwave/I 2 42 , SnCl 2 /SiO 2 43 , I 2 44 , Ultrasound Irradiaton 45 , N H 4 C l 4 6 , ( N H 4 ) 6 M o 7 O 2 4 . 4 H 2 O 4 7 , C i t r i c acid 48 , ionic liquid 49 , Bentonit Clay K-10 50 , AcOH 51 and BSA 52 .…”

Section: Scheme 1 the Preparation Of The Sulfonic Acid Functionalizementioning

confidence: 99%

Synthesis of Quinoxaline Derivatives using Sulfonic Acid Functionalized Imidazolium Salts as Highly Efficient and Reusable Bronsted Acidic Ionic Liquids Catalysts under Solvent-free Conditions

Sajjadifar¹,

Nezhad²,

Khosravani³

2013

Chem Sci Trans

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A simple, highly efficient and green procedure for the condensation of aryl and alkyl 1,2-diamines with α-diketones in the presence of catalytic amount of sulfonic acid functionalized imidazolium salts (SAFIS) is described. Using this method, quinoxaline derivatives as biologically interesting compounds are produced in high to excellent yields and short reaction times. Environmentally benign, simple methodologies, easy workup procedure, clean reaction, short reaction time, high yield and easy preparation of the catalysts are some advantages of this work. In this work, some sulfonic acid functionalized imidazolium salts (SAFIS), as a new category of ionic liquids, are synthesized by eco-friendly and simple procedures, and used as highly efficient and reusable catalysts to promote the following one-pot organic transformations under solvent-free conditions.

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“…5a-j, 6a,b,f,g,i, 7a,b,f,g,i, 11a-e, 12a, 13a agree with those reported in the literature. 37,[40][41][42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57][58] For the NMR spectra of new compounds see the Supporting Information. 6c,d, 7c,d, 12b-e and 13b-e are reported together below with some spectral data of known compounds not yet reported in the literature.…”

Section: Synthesis Of 23-dihydropyrazinesmentioning

confidence: 99%

A Green Synthesis of Quinoxalines and 2,3-Dihydropyrazines

Delpivo¹,

Micheletti²,

Boga³

2013

Synthesis

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Quinoxaline and dihydropyrazine derivatives were obtained in high yields by simple addition of 1,2-diamines and 1,2-dicarbonyl compounds in water. In some cases, the products spontaneously precipitated from the reaction mixture, making it possible to recover and reuse the mother liquor for further condensations. The very mild reaction conditions, the high yields of the products, and the absence of any catalyst make this methodology an efficient and green route to quinoxalines and dihydropyrazines.

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Heterogeneous SnCl₂/SiO₂versus Homogeneous SnCl₂Acid Catalysis in the Benzo[N,N]-heterocyclic Condensation

Cited by 22 publications

References 48 publications

Donor–Acceptor–Donor Thienopyrazines via Pd-Catalyzed C–H Activation as NIR Fluorescent Materials

Donor–Acceptor–Donor Thienopyrazines via Pd-Catalyzed C–H Activation as NIR Fluorescent Materials

Synthesis of Quinoxaline Derivatives using Sulfonic Acid Functionalized Imidazolium Salts as Highly Efficient and Reusable Bronsted Acidic Ionic Liquids Catalysts under Solvent-free Conditions

A Green Synthesis of Quinoxalines and 2,3-Dihydropyrazines

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