157668-05-8Relevant academic research and scientific papers
Intramolecular palladium-catalyzed alkene carboalkynylation
Nicolai, Stefano,Swallow, Peter,Waser, Jerome
supporting information, p. 5959 - 5964 (2015/08/03)
Abstract Carbocycles are essential building blocks for the synthesis of natural and synthetic bioactive compounds. Herein, we report the first example of palladium-catalyzed intramolecular carboalkynylation of non-activated olefins. Using activated carbon
Isonitrile trapping reactions under thermolysis of alkoxyamines for the synthesis of quinolines
Janza, Birgit,Studer, Armido
, p. 1875 - 1878 (2007/10/03)
An efficient tandem radical process comprising a thermal alkoxyamine homolysis, an isonitrile trapping reaction, a 5-exo-trig cyclization, and a homolytic aromatic substitution leads to substituted dihydroquinolines. Depending on the substituent R1, oxidation to dihydro-1H-cyclopenta- [b]quinolines (for R1 = aryl) or tautomerization to tetrahydro-1H-cyclopenta[b]quinolines (for R1 = CO2Me, CN) occurs. The heterocycles are obtained in moderate to good yields. Upon using microwave-induced heating, the reaction time can be shortened from 3 days to 30 min.
Intramolecular Diels-Alder Reaction of N-Alkyl-2-cyano-1-azadienes: A Study of the Eschenmoser Cycloreversion of Dihydrooxazines as a Route to N-Alkyl-2-cyano-1-azadienes
Motorina, Irina A.,Fowler, Frank W.,Grierson, David S.
, p. 2098 - 2105 (2007/10/03)
In connection with the development of the intramolecular Diels-Alder reaction (IMDA) of 1-azadienes, the 5,6-dihydro-4H-1,2-oxazine 12 has been evaluated as a synthon equivalent of the 2-cyano-1-azadiene system. It was found that the dihydrooxazonium salt 27, generated in situ from the cyclic hydroxamic acid derivative 26, is converted directly to azadiene 4a via tautomerization to the corresponding enamine and a particularly facile Eschenmoser type cycloreversion process. Conditions were subsequently found for the preparation of synthon 12. N-Alkylation of this intermediate with alkyl bromides in the presence of Ag+ ion also resulted in direct formation of the 2-cyano-1-azadiene products 38a-d and 4a. Microwave irradiation of a benzene solution of azadiene 4a proved to be a convenient means to effect its IMDA conversion to indolizidine 5a. To avoid decomposition of azadiene 38c, its intramolecular cycloaddition giving 40 (60%) was achieved by flash vacuum thermolysis.
Photoinduced electron transfer (PET) promoted cyclisations of 1-[N-alkyl-N-(trimethylsilyl)methyl]amines tethered to proximate olefin: Mechanistic and synthetic perspectives
Pandey, Ganesh,Devi Reddy,Kumaraswamy
, p. 8185 - 8194 (2007/10/02)
Upon PET reaction, amines of type 1 undergo efficient cyclisations to produce pyrrolidines and piperidines. Mechanistically, involvement of delocalised α-silylmethyl amine radical cation as reactive intermediate in such cyclisations are described.
