158115-67-4Relevant articles and documents
Quinazoline Derivatives by Cyclodehydrogenation of N-(2-Substituted Aryl)-Piperidines
M?hrle,Jeandrée
, p. 1577 - 1588 (2007/10/03)
Dehydrogenation of the N-[2-(aminocarbonyl)phenyl]piperidines 1-5 using Hg(II)-EDTA, generated the quinazolinones 6-9. Increasing size of the 4-substituent in the piperidine decreased the oxidation rate and the product yield. N-[2-(Hydroxyiminomethyl)phenyl]piperidines 18-22 showed a different behaviour. While 18 with Hg(II)-EDTA in water produced the oxime lactam 24 in quantitative yield, the 4-substituted piperidines 19-21 caused not only a lower reaction rate but also an altered product pattern. The double dehydrogenation to lactams was reduced and the cyclic nitrones, formed by two electron withdrawal, became dominant. From the spiro compounds 21 and 22, solely the quinazoline-N-oxides 29 and 30 resulted. The mechanism of the reactions is discussed.
The Stereochemistry of Organometallic Compounds. XL. Rhodium-Catalysed Reactions of Hydrogen and Carbon Monoxide with Alkenylanilines
Anastasiou, Despina,Campi, Eva M.,Chaouk, Hassan,Fallon, Gary D.,Jackson, W. Roy,et al.
, p. 1043 - 1060 (2007/10/02)
Rhodium-catalysed reactions of o- or p-cyano-N-allylanilines with H2/CO give N-arylpyrrolidine aldehydes resulting from a double hydroformylation sequence.In contrast reactions of o- or p-methyl-N-allylanilines or N-allylaniline itself with H2/CO give 'dimeric' compounds resulting from self-condensation reactions of an initially formed hydroformylation product together with varying amounts of the double hydroformylation product.Similar reactions of o-cyano-N-but-3-enylanilines give low yields of double hydroformylation products and major products arising from hydrogenation or cross coupling of intermediate enamines.The structure of one of these products, N-2-cyanophenyl-5-(N'-2-cyanophenyl-3-methylpyrrolidin-2-yl)-1,2,3,4-tetrahydropyridine (17) (IUPAC name: 2--1,2,3,4-tetrahydropyridin-1-yl>benzonitrile) was confirmed by an X-ray single-crystal structure determination.