Synthesis and X-ray powder diffraction data of cis-4-(4-methoxyphenyl)-3-methyl-6-nitro-2-phenyl-1,2,3,4-tetrahydroquinoline

2013 ◽  
Vol 28 (4) ◽  
pp. 307-311 ◽  
Author(s):  
M.A. Macías ◽  
J.A. Henao ◽  
Arnold R. Romero Bohórquez ◽  
Vladimir V. Kouznetsov
Keyword(s):  
Powder Diffraction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Gas Chromatography Mass Spectrometry ◽  
One Pot ◽  
X Ray ◽  
Cell Parameters ◽  
Diels Alder Reaction ◽  
The One ◽  
C Nmr

The 2,4-diaryl 1,2,3,4-tetrahydroquinoline derivative (1), described in the title (Chemical formula: C23H22N2O3), was synthesized via the “one-pot” three-component imino Diels–Alder reaction catalyzed by Cu(OTf)2. Molecular characterization was performed by 1H and 13C NMR, Fourier transform-infrared, and gas chromatography-mass spectrometry. The X-ray powder diffraction pattern for the title compound was analyzed and found to be crystallized in an orthorhombic system with space group P212121 (No. 19) and refined unit-cell parameters a = 8.6415(8) Å, b = 12.679(2) Å, c = 17.601(2) Å, and V = 1928.4(2) Å3.

Synthesis and X-ray powder diffraction data of N-benzyl-6-chloro-4-(4-methoxyphenyl)-3-methyl-1,2,3,4-tetrahydroquinoline

2012 ◽  
Vol 27 (4) ◽  
pp. 269-272 ◽  
Author(s):  
J. A. Pinilla ◽  
J. A. Henao ◽  
M. A. Macías ◽  
Arnold R. Romero Bohórquez ◽  
Vladimir V. Kouznetsov
Keyword(s):  
Powder Diffraction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Gas Chromatography Mass Spectrometry ◽  
Unit Cell Parameters ◽  
X Ray ◽  
Cell Parameters ◽  
Diels Alder Reaction ◽  
C Nmr ◽  
Xrpd Pattern

The N-benzyl-6-chloro-4-(4-methoxyphenyl)-3-methyl-1,2,3,4-tetrahydroquinoline derivative (chemical formula: C24H24ClNO) was obtained from cationic imino Diels–Alder reaction catalyzed by BF3.OEt2. Molecular characterization was performed by 1H and 13C NMR, Fourier transform-infrared and gas chromatography-mass spectrometry. The X-ray powder diffraction (XRPD) pattern for the new compound was analyzed and found to be crystallized in an orthorhombic system with space group Fdd2 (No. 43) and refined unit-cell parameters a = 33.053(7) Å, b = 41.558(9) Å, c = 5.841(1) Å and V = 8023(2) Å3.

Proline triflate catalysed Diels–Alder reaction in the synthesis of tetrahydroquinoline derivatives

2009 ◽  
Vol 2009 (8) ◽  
pp. 499-504 ◽  
Author(s):  
Jianjun Li ◽  
Jia Li ◽  
Weike Su
Keyword(s):  
Aromatic Amines ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
One Pot Synthesis ◽  
Diels Alder Reaction ◽  
The One ◽  
High Stereoselectivity

Proline triflate was found to catalyse efficiently the one-pot synthesis of 2H-pyranotetrahydroquinolines from aryl imines, and 3,4-dihydro-2 H-pyran with high stereoselectivity. The aryl imines were formed in situ from aromatic amines and arylaldehydes.

scholarly journals Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction

2021 ◽  
Vol 17 ◽  
pp. 2425-2432
Author(s):  
Ren-Jie Fang ◽  
Chen Yan ◽  
Jing Sun ◽  
Ying Han ◽  
Chao-Guo Yan
Keyword(s):  
Room Temperature ◽  
Alder Reaction ◽  
Diels Alder ◽  
Efficient Synthesis ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Acid Catalyzed ◽  
The One ◽  
High Yields ◽  
Ddq Oxidation

The p-TsOH-catalyzed Diels–Alder reaction of 3-(indol-3-yl)maleimides with chalcone in toluene at 60 °C afforded two diastereoisomers of tetrahydropyrrolo[3,4-c]carbazoles, which can be dehydrogenated by DDQ oxidation in acetonitrile at room temperature to give the aromatized pyrrolo[3,4-c]carbazoles in high yields. On the other hand, the one-pot reaction of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones with chalcones or benzylideneacetone in acetonitrile in the presence of p-TsOH and DDQ resulted in polyfunctionalized carbazoles in satisfactory yields. The reaction mechanism included the DDQ oxidative dehydrogenation of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones to the corresponding 3-vinylindoles, their acid-catalyzed Diels–Alder reaction and sequential aromatization process.

scholarly journals Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels-Alder reaction

2021 ◽  
Author(s):  
Ren-Jie Fang ◽  
Chen Yan ◽  
Jing Sun ◽  
Ying Han ◽  
Chao-Guo Yan
Keyword(s):  
Room Temperature ◽  
Alder Reaction ◽  
Diels Alder ◽  
Efficient Synthesis ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Acid Catalyzed ◽  
The One ◽  
High Yields ◽  
Ddq Oxidation

p-TsOH catalyzed Diels-Alder reaction of 3-(indol-3-yl)maleimides with chalcone in toluene at 60 oC afforded two diastereoisomers of tetrahydropyrrolo[3,4-c]carbazoles, which can be dehydrogenated by DDQ oxidation in acetonitrile at room temperature to give the aromatized pyrrolo[3,4-c]carbazoles in high yields. On the other hand, the one-pot reaction of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones with chalcones in acetonitrile in the presence of p-TsOH and DDQ resulted in polyfunctionalized carbazoles in satisfactory yields. The reaction mechanism included DDQ oxidative dehydrogenation of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones to the corresponding 3-vinylindoles, its acid-catalyzed Diels-Alder reaction and sequential aromatization process.

Facile One-Pot Synthesis and Crystal Structure of 2:1 Adducts of Myrcene (or Ocimene) with Benzoquinones

2020 ◽  
Vol 17 (8) ◽  
pp. 624-627
Author(s):  
Sujata V. Bhat ◽  
Rohan S. Pawar ◽  
P. Rajakannu
Keyword(s):  
Crystal Structure ◽  
Single Crystal ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Synthesis And Crystal Structure ◽  
X Ray ◽  
One Pot Synthesis ◽  
Diels Alder Reaction

One-pot tandem oxidation and double Diels-Alder reaction of myrcene or ocimene with in situ generated 1,4-benzoquinone or 1,2-benzoquinone at 0°C for 1.5 h yielded polyalkylated 1,4,4a,5,8,8a,9a,10a-octahydro-9,10-anthracenediones and bis(alkylated) 9,10-phenanthrenedione respectively. The structure of novel bis-adduct from ocimene, (1R,4aR,5S,8aS,9aS,10aR)-rel- 1,4,4a,5,8,8a,9a,10a-octahydro-2,6-dimethyl-1,5-bis(3-methyl-2-buten-1-yl)-9,10-anthracenedione, was elucidated through single crystal X-ray analysis.

scholarly journals Preparación simple de nuevas N-(6-metil-2-nitrofenil-1,2,3,4-tetrahidroquinolin-4-il) pirrolidin-2-onas y su análisis espectroscópico. Objetivos.

2011 ◽  
Vol 16 (2) ◽  
pp. 160 ◽  
Author(s):  
John H. Bermudez ◽  
José Luis Pinto ◽  
Carlos Mario Meléndez ◽  
José A. Henao ◽  
Vladimir V. Kouznetsov
Keyword(s):  
Cycloaddition Reaction ◽  
2D Nmr ◽  
Alder Reaction ◽  
Diels Alder ◽  
Nmr Studies ◽  
One Pot ◽  
Isolation And Purification ◽  
One Pot Synthesis ◽  
Diels Alder Reaction ◽  
The One

<p><strong>Objectives. </strong>To prepare new N-(1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-one molecules and to characterize them by spectroscopic methods. <strong>Materials and methods. </strong>All reagents were purchased from Aldrich, commercial grade. The purity of the products and the composition of the reaction mixtures were monitored by thin layer chromatography over Silufol UV<sub>254</sub> chromatoplates (0.25 mm). Product isolation and purification were performed by column chromatography (SiO<sub>2</sub>), using ethyl acetate. <strong>Results.</strong> Preparation of new N-(2-nitrophenyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-ones has been achieved via the one-pot synthesis, based on a BiCl<sub>3</sub>-catalyzed imino Diels-Alder cycloaddition reaction of toluidine, N-vinylpyrrolidin-2-one and 4-nitro- or 3-nitrobenzaldehydes. The structure of the pyrrolidine derivatives was confirmed by <sup>1</sup>H nmr and <sup>13</sup>C nmr studies, in addition to inverse-detected 2D NMR experiments and monocrystal X-ray diffraction. <strong>Conclusions. </strong>An efficient, economic, and fast synthetic route (multi-component imino Diels-Alder reaction) was employed in the construction of several new tetrahydroquinoline derivatives, useful and attractive rigid skeleton with well-defined stereochemistry.</p> <p> </p> <p><strong>Key words: </strong>tetrahydroquinoline derivatives, N-substituted pyrrolidin-2-ones, three component imino Diels-Alder reaction, one-pot synthesis.</p>

scholarly journals One-pot cross-enyne metathesis (CEYM)–Diels–Alder reaction of gem-difluoropropargylic alkynes

2013 ◽  
Vol 9 ◽  
pp. 2688-2695 ◽  
Author(s):  
Santos Fustero ◽  
Paula Bello ◽  
Javier Miró ◽  
María Sánchez-Roselló ◽  
Günter Haufe ◽  
...  
Keyword(s):  
Research Group ◽  
Alder Reaction ◽  
Diels Alder ◽  
Internal Source ◽  
Enyne Metathesis ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Heterocyclic Derivatives ◽  
The One

Propargylic difluorides 1 were used as starting substrates in a combination of cross-enyne metathesis and Diels–Alder reactions. Thus, the reaction of 1 with ethylene in the presence of 2nd generation Hoveyda–Grubbs catalyst generates a diene moiety which in situ reacts with a wide variety of dienophiles giving rise to a small family of new fluorinated carbo- and heterocyclic derivatives in moderate to good yields. This is a complementary protocol to the one previously described by our research group, which involved the use of 1,7-octadiene as an internal source of ethylene.

Aza-Diels-Alder Reaction Between 1,2-Diaza-1,3-dienes and β-Aryl-α,β-unsaturated Carbonyl Compounds. Easy One-pot Entry to 2’-Oxo-imidazo[1’,5’- f]tetrahydropyridazine

2014 ◽  
Vol 10 (6) ◽  
pp. 951-960
Author(s):  
Orazio Attanasi ◽  
Luca Bianchi ◽  
Maurizio D’Auria ◽  
Gianfranco Favi ◽  
Fabio Mantellini ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Diels Alder Reaction
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