Stereoselective synthesis of pyrano[3,2-c]- and furano[3,2-c]quinolines: Samarium diiodide-catalyzed one-pot aza-Diels-Alder reactions
Three-component aza-Diels-Alder reactions involving aromatic aldehydes, aromatic amines, and dihydropyran or dihydrofuran are effectively catalyzed by samarium diiodide to afford pyrano[3,2-c]- or furano[3,2-c]quinolines in good yields and with high stere
Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza-Diels-Alder Cycloaddition
Electrochemical synthesis of cyclic ether-annulated tetrahydroquinolines from imines and cyclic ethers in an undivided cell under constant current conditions was developed. The electrosynthesis proceeds via the enol ether formation from ethers following the aza-Diels-Alder [4+2] cycloaddition. The method is applicable to a wide range of imines and results in the desired products in yields of 23 to 75%. In situ preparation of imines from the corresponding anilines and aldehydes led to mostly the same yields of tetrahydroquinolines. No cycloaddition products were formed using the chemical oxidants. Synthesized cyclic ether-annulated tetrahydroquinolines exhibit high antifungal activity, which is superior to the commercial fungicide Triadimefon. (Figure presented.).
Alekseenko, Anna L.,Baberkina, Elena P.,Glinushkin, Alexey P.,Grishin, Sergei S.,Kovalenko, Alexey E.,Terent'ev, Alexander O.,Vil', Vera A.
supporting information
(2022/01/26)
Ceric Ammonium Nitrate (CAN)-Catalyzed, Efficient, One-Pot, Three-Component, aza-Diels-Alder Reactions for a Facile Synthesis of Tetrahydropyranoquinoline Derivatives
A simple, efficient, and cost-effective method for the synthesis of tetrahydropyranoquinoline derivatives by a one-pot condensation of aromatic aldehyde, aromatic amine, and 3,4-dihydro-2H-pyran respectively in the presence of ceric ammonium nitrate (CAN)
Controllable stereoselective synthesis of cis or trans pyrano and furano tetrahydroquinolines: Polyaniline-p-toluenesulfonate salt catalyzed one-pot aza-Diels-Alder reactions
cis as well as trans pyrano tetrahydroquinolines were synthesized using a polymeric solid acid catalyst, polyaniline-p-toluenesulfonate (PANI-PTSA) salt, by conveniently controlling the reaction conditions. One-pot three component aza-Diels-Alder reaction
Palaniappan, Srinivasan,Rajender, Boddula,Umashankar, Male
experimental part
p. 70 - 74
(2012/02/03)
Samarium triflate as mild and efficient catalyst for aza-diels-alder reaction: A facile synthesis of cis-fused pyrano-and furanoquinolines
Three-component coupling reactions of aldehydes, amines, and cyclic enol ethers have been carried out in the presence of samarium triflate to afford the corresponding pyrano and furanoquinolines in excellent yields with high endo-selectivity. The reaction
Narsaiah, A. Venkat,Reddy, A. Ramesh,Reddy, B. V. Subba,Yadav
experimental part
p. 1750 - 1757
(2010/07/05)
Stereoselective synthesis of pyrano[3,2-c]- and furano[3,2-c]quinolines: Gadolinium chloride catalyzed one-pot aza-Diels-Alder reactions
A simple and efficient method for the cis-selective synthesis of pyrano- and furano[3,2-c]quinolines via gadolinium chloride catalyzed onepot aza-Diels-Alder reaction is described. Solvent conditions played amajor role in affecting the diastereoselectivity of the products.
Yu, Yong,Zhou, Jun,Yao, Zhigang,Xu, Fan,Shen, Qi
p. 351 - 354
(2011/04/22)
Phosphomolybdic acid-catalyzed efficient one-pot three-component aza-Diels-Alder reactions under solvent-free conditions: a facile synthesis of trans-fused pyrano- and furanotetrahydroquinolines
trans-Fused pyrano- and furanotetrahydroquinoline derivatives have been synthesized via a one-pot three-component aza-Diels-Alder reaction of aryl imines formed in situ from aromatic amines and arylaldehydes with cyclic enol ethers,such as 3,4-dihydro-2H-
Nagaiah,Sreenu,Rao, R. Srinivasa,Vashishta,Yadav
p. 4409 - 4413
(2007/10/03)
Aza-Diels-Alder reactions in ionic liquids: A facile synthesis of pyrano- and furanoquinolines
Room temperature ionic liquids are found to catalyze efficiently the three component-coupling reactions of aldehydes, amines and cyclic enol ethers such as 3,4-dihydro-2H-pyran and 2,3-dihydrofuran under mild and convenient conditions to afford the corres
Yadav,Reddy,Reddy,Rao, R. Srinivasa
p. 1599 - 1604
(2007/10/03)
Novel Use of Selectfluor for the Synthesis of cis-Fused Pyrano- and Furanotetrahydroquinolines
Aryl imines formed in situ from aryl aldehydes and aromatic amines undergo smooth [4 + 2] cycloaddition reactions with cyclic enol ethers such as 3,4-dihydro-2H-pyran and 2,3-dihydrofuran in the presence of 10 mol % Selectfluor in acetonitrile at room tem
Yadav,Reddy,Sunitha,Reddy
p. 1203 - 1206
(2007/10/03)
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