Synthesis of Pyranoquinolines from One-Pot Imino-Diels-Alder Reaction catalyzed by LaCl3.7H2O
Year
: 2014
Abstract: The Hetero-Diels-Alder reaction is one of the most powerful synthetic routes for constructing nitrogen containing sixmembered heterocycles [1]. In recent years, increasing attention has been given to the synthesis of pyrano[3,2-c] tetrahydroquinolines via three component aza-Diels–Alder reactions of aryl aldehyde, aryl amine with cyclic enol ethers. pyrano quinolone derivatives are an important class of natural products and exhibit spectrum of biological activities, such as antiallergic, anti-inflammatory, antipyretic, analgesic, antiplatelet, psychotropic, estrogenic activity anti-arrhythmic, immunosuppressive and anticancer properties [2]. In addition to this they are also used in pharmaceuticals [3].
In this report, we describe a novel and highly efficient method for the one-pot synthesis of pyranoquinolines using a catalytic amount of LaCl3 .7H2O. Thus treatment of aniline with 3,4-dihydro-2H-pyran (DHP) in the presence of 5 mol% lanthanum trichloride in acetonitrile under reflux afforded the corresponding pyrano[3,2-c]quinolone derivatives endo and exo in 90% yield (Scheme 1).
RNH2NHONHOOHOHHHHHRRCH3CNLaCl3.7H2Orefluxendo(major)exo(minor)O
(Scheme1)
References
[1]. Yadav, J. S.; Reddy, B. V. S.; Srinivasa Rao, R.; Kiran Kumar, S.; Kunwarb, A. C. InClR3R
Catalyzed hetero-Diels–Alder reaction: an expeditious synthesis of pyranoquinolines. Tetrahedron.
2002, 58, 7891-7896.
[2]. Palaniappan, S.; Rajender,B.; Umashankar, M. Controllable stereoselective synthesis of cis or trans pyrano and furano tetrahydroquinolines: Polyaniline-p-toluenesulfonate salt catalyzed one-pot aza-Diels–Alder reactions. J. Mol. Catal. A-Chem. 2012, 352, 70-74.
0B[3]. Michael, J.P. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 2005, 22, 627-646
In this report, we describe a novel and highly efficient method for the one-pot synthesis of pyranoquinolines using a catalytic amount of LaCl3 .7H2O. Thus treatment of aniline with 3,4-dihydro-2H-pyran (DHP) in the presence of 5 mol% lanthanum trichloride in acetonitrile under reflux afforded the corresponding pyrano[3,2-c]quinolone derivatives endo and exo in 90% yield (Scheme 1).
RNH2NHONHOOHOHHHHHRRCH3CNLaCl3.7H2Orefluxendo(major)exo(minor)O
(Scheme1)
References
[1]. Yadav, J. S.; Reddy, B. V. S.; Srinivasa Rao, R.; Kiran Kumar, S.; Kunwarb, A. C. InClR3R
Catalyzed hetero-Diels–Alder reaction: an expeditious synthesis of pyranoquinolines. Tetrahedron.
2002, 58, 7891-7896.
[2]. Palaniappan, S.; Rajender,B.; Umashankar, M. Controllable stereoselective synthesis of cis or trans pyrano and furano tetrahydroquinolines: Polyaniline-p-toluenesulfonate salt catalyzed one-pot aza-Diels–Alder reactions. J. Mol. Catal. A-Chem. 2012, 352, 70-74.
0B[3]. Michael, J.P. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 2005, 22, 627-646
Keyword(s): Lanthanum reagents,Hetero-Diels–Alder reaction,Tetrahydroquinolines
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Synthesis of Pyranoquinolines from One-Pot Imino-Diels-Alder Reaction catalyzed by LaCl3.7H2O
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| contributor author | ناعمه نعیمی | en |
| contributor author | حسین عشقی | en |
| contributor author | اعظم کریمیان | en |
| contributor author | naemeh naeimi | fa |
| contributor author | Hossein Eshghi | fa |
| contributor author | azam karimian | fa |
| date accessioned | 2020-06-06T14:15:34Z | |
| date available | 2020-06-06T14:15:34Z | |
| date copyright | 8/19/2014 | |
| date issued | 2014 | |
| identifier uri | https://libsearch.um.ac.ir:443/fum/handle/fum/3389078 | |
| description abstract | The Hetero-Diels-Alder reaction is one of the most powerful synthetic routes for constructing nitrogen containing sixmembered heterocycles [1]. In recent years, increasing attention has been given to the synthesis of pyrano[3,2-c] tetrahydroquinolines via three component aza-Diels–Alder reactions of aryl aldehyde, aryl amine with cyclic enol ethers. pyrano quinolone derivatives are an important class of natural products and exhibit spectrum of biological activities, such as antiallergic, anti-inflammatory, antipyretic, analgesic, antiplatelet, psychotropic, estrogenic activity anti-arrhythmic, immunosuppressive and anticancer properties [2]. In addition to this they are also used in pharmaceuticals [3]. In this report, we describe a novel and highly efficient method for the one-pot synthesis of pyranoquinolines using a catalytic amount of LaCl3 .7H2O. Thus treatment of aniline with 3,4-dihydro-2H-pyran (DHP) in the presence of 5 mol% lanthanum trichloride in acetonitrile under reflux afforded the corresponding pyrano[3,2-c]quinolone derivatives endo and exo in 90% yield (Scheme 1). RNH2NHONHOOHOHHHHHRRCH3CNLaCl3.7H2Orefluxendo(major)exo(minor)O (Scheme1) References [1]. Yadav, J. S.; Reddy, B. V. S.; Srinivasa Rao, R.; Kiran Kumar, S.; Kunwarb, A. C. InClR3R Catalyzed hetero-Diels–Alder reaction: an expeditious synthesis of pyranoquinolines. Tetrahedron. 2002, 58, 7891-7896. [2]. Palaniappan, S.; Rajender,B.; Umashankar, M. Controllable stereoselective synthesis of cis or trans pyrano and furano tetrahydroquinolines: Polyaniline-p-toluenesulfonate salt catalyzed one-pot aza-Diels–Alder reactions. J. Mol. Catal. A-Chem. 2012, 352, 70-74. 0B[3]. Michael, J.P. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 2005, 22, 627-646 | en |
| language | English | |
| title | Synthesis of Pyranoquinolines from One-Pot Imino-Diels-Alder Reaction catalyzed by LaCl3.7H2O | en |
| type | Conference Paper | |
| contenttype | External Fulltext | |
| subject keywords | Lanthanum reagents | en |
| subject keywords | Hetero-Diels–Alder reaction | en |
| subject keywords | Tetrahydroquinolines | en |
| identifier link | https://profdoc.um.ac.ir/paper-abstract-1043442.html | |
| conference title | The 22nd Iranian Seminar of Organic Chemistry | en |
| conference location | تبریز | fa |
| identifier articleid | 1043442 |