One-pot multicomponent synthesis of some 5,6-dihydro-benzo[h]quinoline derivatives

Almutairi, Tahani Mazyad; Al-Hazimi, Hassan M.; El-Baih, Fatma E.M.

doi:10.1016/j.jscs.2009.06.001

Cited by 12 publications

(9 citation statements)

References 16 publications

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“…It has been reported [27,28] that 5,6-dihydrobenzo[h]quinoline derivatives are prepared by condensation of the corresponding 2-arylidene-1-tetralone with malononitrile in the presence of ammonium acetate or via one-pot multicomponent reactions (MCRs) of aldehydes, malononitrile, 1-tetralone and ammonium acetate. However, we found that one-pot MCRs of aldehydes, malononitrile, 1-tetralone and ammonium acetate yielded the corresponding phenanthrene derivatives instead of the expected 5,6-dihydrobenzo[h]quinolines (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

An Efficient Approach to the Synthesis of Highly Congested 9,10-Dihydrophenanthrene-2,4-dicarbonitriles and Their Biological Evaluation as Antimicrobial Agents

et al. 2013

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An efficient and novel method for the synthesis in moderate to good yield (72%-84%) of a series of 3-amino-1-substituted-9,10-dihydrophenanthrene-2,4-dicarbonitriles 1-5 via one-pot multi-component reactions of aldehydes, malononitrile, 1-tetralone and ammonium acetate has been delineated. Cyclocondensation attempts of aminocyanophenanthrene derivatives 1, 2, 4 and 5 with acetic anhydride in the presence of conc. H 2 SO 4 failed and instead the diacetylamino derivatives 10-13 were obtained. All prepared compounds were structurally elucidated by various spectroscopic methods and X-ray crystallography. N,N-diacetylamino-derivatives of phenanthrene have shown good antimicrobial activity.

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Section: Resultsmentioning

confidence: 99%

An Efficient Approach to the Synthesis of Highly Congested 9,10-Dihydrophenanthrene-2,4-dicarbonitriles and Their Biological Evaluation as Antimicrobial Agents

et al. 2013

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“…Compound 5c was recrystallized from petroleum ether 60-80 °C 25 . Synthesis of 2-arylidenemalononitriles (8): They were synthesized by reaction of aromatic aldehyde with malononitrile according to the literature procedures 26 .…”

Section: Synthesis Of 2-[(35-disubstituted 1-phenyl-1h-pyrazol-4-yl)mentioning

confidence: 99%

“…Attempts were made to prepare 6-amino-3-propyl-1-(2pyridinyl)-4-(3',4',5'-trimethoxy-phenyl)-1H-pyrazolo[3,4b]pyridine-5-carbonitrile (10) by one pot four component reaction using traditional reflux method, microwave and ultrasound irradiation of mixture aldehyde 7a, pyrazolone 2e and malononitrile in the presence of ammonium acetate were not successful 26 . Instead we obtained the same product 9a as indicated by the 1 H NMR data of the reaction product (Scheme-II).…”

Section: -Aminomentioning

confidence: 99%

“…Cyclization of 9a,b with acetic anhydride in the presence of conc. H2SO4 afforded pyrano[2,3-d]pyrimidin-5-one derivatives 11a,b 26 (Scheme-II). IR spectrum of these compounds exhibited the absence of stretching band of cyano group and a broad absorption bands of the NH/OH stretching in the region of 3484-3449 cm -1 beside bands at the range of 1625-1655 cm -1 due to C=O stretching.…”

Section: -Aminomentioning

confidence: 99%

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Synthesis of Some Novel Pyrazolopyridooxazine, Pyrazoloquinolizines, Pyrazoloindolizine and Pyrazolopyranopyrimidinone Derivatives

Al-Tilasi¹,

El-Baih²

2014

Asian J. Chem.

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Several heterocyclic compounds containing pyrazole ring are very useful as intermediates for pharmaceuticals 1-4 and have shown several biological activities such as antiinflammatory agents 5-7 , antibacterial 8-12 , antifungal 9 , antiviral 13,14 , antitumor 15-19 and insecticidal 20,21. Numerous pyrazole derivatives are also used in dye industry 22. In our continued interest in the development of highly expedient methods for the synthesis of diverse heterocyclic compounds of biological significance, we report herein the synthesis of some novel pyrazole derivatives which are pyrazolinoquinolizines, 1,4-oxazinopyrazolines, 6-amino-1,4dihydro-pyrano[2,3-c]pyrazole-5-carbonitrile and 4,6dihydropyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidin-5(1H)-one. Moreover, in some cases we used a one pot multicomponents reaction using microwave and ultrasound irradiation. EXPERIMENTAL Melting points were determined using an Electrothermal IA9000 series digital capillary melting point apparatus and are uncorrected. IR spectra were obtained as KBr discs on a 1000-Perkin Elmer FT-IR spectrophotometer. 1 H NMR and 13 C NMR spectra were recorded on a JEOL ECP-300 NMR in CDCl3 (or DMSO-d6) using TMS as an internal standard. Chemical shifts are given in ppm on the δ scale and coupling constants (J) are given in Hz. Electron impact (EI) MS spectra were acquired with the aid of a Shimadzu GCMSQP5050A spectrometer, equipped with a 30 m × 0.25 mm DB-1 glass column, operating with an ionization energy of 70 eV, at the

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“…26 In another approach, partially reduced benzo[h]quinolines were obtained by reaction of arylidenes and 1-tetralone in the presence of ammonium acetate and sodium methoxide. 27 Benzo[h]quinolines have also been afforded by reaction of 6-methoxy-1-tetralone and methyl propiolate in saturated ammonical methanol. 28 Ram and co-workers reported the synthesis of partially reduced benzo[h]quinolines by reaction of 5,6-dihydro-2oxobenzo[h]chromenes with formamidine or benzamidine and S-methylisothiourea under basic conditions.…”

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confidence: 99%

Substituent-Dependent Chemoselective Synthesis of Highly Functionalized Benzo[h]quinolines and 4-Benzylpyrans from 2-Methyl-5-nitro-benzonitrile

Panwar¹,

Shaw²,

Elagamy³

et al. 2018

SynOpen

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A facile, efficient and atom-economic synthesis of highly substituted benzo[h]qninolines was established by reaction of 2-methyl-5-nitrobenzonitrile with suitably functionalized 2H-pyran-2-ones under basic conditions. We observed that the presence of a thiomethyl group at the C-4 position of pyran provides 6-aryl-4-(2-cyano-4-nitrobenzyl)-2-oxo-2H-pyran-3-carbonitrile exclusively without any trace of benzo[h]quinolines. Depending on the nature of the functional group at C-4 of the pyran ring, different products were achieved. To probe the mechanism, we performed control experiments and isolated 3-(1-amino-7-nitro-3-thiophen-2-yl-naphthalen-2-yl)-3-piperidin-1-yl-acrylonitrile, which, on further treatment with base, provided the benzo[h]quinolines. The structure of one the products was characterized by single-crystal X-ray diffraction.

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One-pot multicomponent synthesis of some 5,6-dihydro-benzo[h]quinoline derivatives

Cited by 12 publications

References 16 publications

An Efficient Approach to the Synthesis of Highly Congested 9,10-Dihydrophenanthrene-2,4-dicarbonitriles and Their Biological Evaluation as Antimicrobial Agents

An Efficient Approach to the Synthesis of Highly Congested 9,10-Dihydrophenanthrene-2,4-dicarbonitriles and Their Biological Evaluation as Antimicrobial Agents

Synthesis of Some Novel Pyrazolopyridooxazine, Pyrazoloquinolizines, Pyrazoloindolizine and Pyrazolopyranopyrimidinone Derivatives

Substituent-Dependent Chemoselective Synthesis of Highly Functionalized Benzo[h]quinolines and 4-Benzylpyrans from 2-Methyl-5-nitro-benzonitrile

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One-pot multicomponent synthesis of some 5,6-dihydro-benzo[h]quinoline derivatives

Cited by 12 publications

References 16 publications

An Efficient Approach to the Synthesis of Highly Congested 9,10-Dihydrophenanthrene-2,4-dicarbonitriles and Their Biological Evaluation as Antimicrobial Agents

An Efficient Approach to the Synthesis of Highly Congested 9,10-Dihydrophenanthrene-2,4-dicarbonitriles and Their Biological Evaluation as Antimicrobial Agents

Synthesis of Some Novel Pyrazolopyridooxazine, Pyrazoloquinolizines, Pyrazoloindolizine and Pyrazolopyranopyrimidinone Derivatives

Substituent-Dependent Chemoselective Synthesis of Highly Functionalized­ Benzo[h]quinolines and 4-Benzylpyrans from 2-Methyl-5-nitro-benzonitrile

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Substituent-Dependent Chemoselective Synthesis of Highly Functionalized Benzo[h]quinolines and 4-Benzylpyrans from 2-Methyl-5-nitro-benzonitrile