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.

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.

Four-step one-pot catalytic asymmetric synthesis of multisubstituted tricyclic compounds: Lipase-catalyzed dynamic kinetic resolution followed by an intramolecular Diels–Alder reaction

Synlett ◽  
2021 ◽  
Author(s):  
Izuru Tsuchimochi ◽  
Shuhei Hori ◽  
Yasuo Takeuchi ◽  
Masahiro Egi ◽  
Tomo-o Satoh ◽  
...  
Keyword(s):  
Hydroxy Group ◽  
Kinetic Resolution ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Tricyclic Compounds ◽  
High Yields ◽  
Group Migration ◽  
Oxovanadium Compounds

Starting from readily available tertiary alcohols, four different reactions (i.e., a 1,3-migration of a hydroxy group, kinetic resolution, racemization, and an intramolecular Diels–Alder reaction) took place under the co-catalysis of lipase and oxovanadium compounds in a one-pot process to produce multisubstituted tricyclic carbon frameworks in high yields and high enantioselectivities. The key to the success of this process was the discovery that the silyl group attached to the terminal carbon of the vinyl moiety completely controls the direction of hydroxy group migration.

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.

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