Aqueous SDS micelle-promoted acid-catalyzed domino ABB′ imino Diels–Alder reaction: a mild and efficient synthesis of privileged 2-methyl-tetrahydroquinoline scaffolds

2013 ◽  
Vol 11 (22) ◽  
pp. 3655 ◽  
Author(s):  
Diego R. Merchán Arenas ◽  
Carlos A. Martínez Bonilla ◽  
Vladimir V. Kouznetsov
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Efficient Synthesis ◽  
Diels Alder Reaction ◽  
Acid Catalyzed ◽  
Sds Micelle

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.

Heteropoly acid-catalyzed three-component aza-Diels–Alder reaction in a continuous micro-flow system

RSC Advances ◽  
2015 ◽  
Vol 5 (72) ◽  
pp. 58798-58803 ◽  
Author(s):  
Wei He ◽  
Zheng Fang ◽  
Zhao Yang ◽  
Dong Ji ◽  
Kai Guo
Keyword(s):  
Water Absorption ◽  
Heteropoly Acid ◽  
Phosphotungstic Acid ◽  
Flow System ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
System P ◽  
Micro Flow ◽  
Acid Catalyzed

The first direct aza-Diels–Alder reaction catalyzed using phosphotungstic acid combined with a water absorption device in a micro-flow system was reported.

Asymmetric synthesis of N-phenylethyl-2-phenyldecahydroquinolin-4-ones via Lewis acid catalyzed imino-Diels–Alder reaction

2000 ◽  
Vol 11 (12) ◽  
pp. 2509-2523 ◽  
Author(s):  
Renée Paugam ◽  
Emmanuelle Valenciennes ◽  
Linda Le Coz-Bardol ◽  
Jean-Christophe Garde ◽  
Lya Wartski ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Lewis Acid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Acid Catalyzed

An Efficient Synthesis of New C-2 Aryl-Substituted Quinolines Based on Three-Component Imino Diels—Alder Reaction.

ChemInform ◽  
2006 ◽  
Vol 37 (24) ◽  
Author(s):  
Vladimir Kouznetsov ◽  
Arnold R. Romero Bohorquez ◽  
Luis Astudillo Saavedra ◽  
Ricardo Fierro Medina
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Efficient Synthesis ◽  
Diels Alder Reaction ◽  
Substituted Quinolines
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