- Photoinitiated Radical-Forming Reactions of 2-Quinolinecarbonitrile At 77 and 331 K
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The photoinitiated dimerization of 2-quinolinecarbonitrile (1) in HCl-acidified 2-propanol/water (4:1) has been studied at 77 and 331 K at 250, 300 and 350 nm in unsensitized and benzophenone- and biphenyl-sensitized reactions.One principal product, a dimer lactam (5), is formed at all wavelengths through a triplet state of 1.ESR spectra taken in ethanol at 77 K show a signal for ethyl radical which is formed by a biphotonic process with 1 in acid solution.A mechanism is proposed for the reaction at 331 K which involves an electron transfer from 2-propanol to an upper triplet state of 1.
- Caronna, Tullio,Morrocchi, Sergio,Vittimberga, Bruno M.
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- Remote control of the C-3-C-4 double-bond epoxidation of a chiral 1,2-dihydroquinoline: Application to the synthesis of (-)-(r)-sumanirole (PNU-95666E)
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A twelve-step synthesis of (-)-(R)-sumanirole starting from quinoline is described. The first synthetic approach, using a chiral Reissert adduct, was too problematic to be pursued further. In the second successful approach, the authors took advantage of the stereoselective epoxidation of a 1,2-dihydroquinoline bearing an Evans' chiral auxiliary at N-1. A twelve-step synthesis of (-)-(R)-sumanirole hydrochloride has been developed from quinoline. In the successful approach, the key reaction is a diastereoselective epoxidation of the C-3-C-4 double bond of a 1,2-dihydroquinoline bearing a chiral oxazolidinone-derived auxiliary at N-1.
- Jean-Gerard, Ludivine,MacE, Frederic,Ngo, Anh Ngoc,Pauvert, Mickael,Dentel, Helene,Evain, Michel,Collet, Sylvain,Guingant, Andre
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supporting information; experimental part
p. 4240 - 4248
(2012/09/08)
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- 2-substituted-1-acyl-1,2-dihydroquinoline derivatives
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This invention relates to the use of 2-substituted-1-acyl-1,2-dihydroquinoline derivatives to increase high density lipoprotein cholesterol (HDL-C) concentration and as therapeutic compositions for treating atherosclerotic conditions such as dyslipoprotei
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- REISSERT COMPOUND STUDIES LXIII: PREPARATION OF REISSERT COMPOUNDS USING DIETHYLALUMINIUM CYANIDE
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Reissert compounds and analogs were synthesized from the reaction of acid halide, heterocyclic base and diethylaluminium cyanide.This new method of Reissert compound synthesis gave yields comparable to other synthetic routes.
- Duarte, Frederick F.,Popp, Frank D.
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p. 723 - 726
(2007/10/02)
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- REISSERT COMPOUND STUDIES. LIII. A NEW SYNTHESIS OF REISSERT COMPOUNDS USING TRI-n-BUTYLTIN CYANIDE
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Reissert compounds were prepared by the reaction of the heterocyclic base and acyl halide with tri-n-butyltin cyanide in methylene chloride.
- Popp, Frank D.,Kant, Joydeep
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p. 2193 - 2195
(2007/10/02)
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- UTILIZATION OF ACETONE CYANOHYDRIN IN THE REISSERT REACTION
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A modification of the Reissert reaction based on the utilization of acetone cyanohydrin instead of potassium cyanide is proposed.
- Sergovskaya, N. L.,Tsizin, Yu. S.,Chernyak, S. A.
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p. 654 - 655
(2007/10/02)
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