4533-41-9Relevant academic research and scientific papers
Copper-catalyzed pyrrole synthesis from 3,6-dihydro-1,2-oxazines
Yasukawa, Naoki,Kuwata, Marina,Imai, Takuya,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 4409 - 4413 (2018/10/17)
Highly-functionalized pyrroles could be effectively synthesized from 3,6-dihydro-1,2-oxazines using a heterogeneous copper on carbon (Cu/C) under neat heating conditions. Furthermore, the in situ formation of 3,6-dihydro-1,2-oxazines via the hetero Diels-Alder reaction between nitroso dienophiles and 1,3-dienes and the following Cu/C-catalyzed pyrrole synthesis also provided the corresponding pyrrole derivatives in a one-pot manner.
Cu(I)/Cu(II)-catalyzed allylic amination of alkenes
Srivastava, Radhey S.,Bertrand III, Roy,Gallo, August A.,Nicholas, Kenneth M.
experimental part, p. 3478 - 3480 (2011/07/08)
Allylic hydrocarbons are selectively converted to the corresponding allyl amines in good to excellent yield by reaction with aryl hydroxylamines catalyzed by a 1:1 mixture of CuCl and CuCl2 (10 mol %). Under these conditions unsymmetrical olefi
Synthesis of oxazines and N-arylpyrroles by reaction of unfunctionalized dienes with nitroarenes and carbon monoxide, catalyzed by palladium-phenanthroline complexes
Ragaini, Fabio,Cenini, Sergio,Brignoli, Daniela,Gasperini, Michela,Gallo, Emma
, p. 460 - 466 (2007/10/03)
The reaction between an unfunctionalized conjugated diene and a nitroarene under CO pressure and at 100 °C, catalyzed by [Pd(Phen)2][BF4]2 (Phen = 1,10-phenanthroline), affords the corresponding hetero-Diels -Alder adduct (oxazine) in up to 91% yields in one pot. If the reaction mixture is then heated to 200 °C, the oxazines are converted into the corresponding N-arylpyrroles in good yields. Pressures as low as 5 bar can be employed, and 0.08% catalyst is sufficient to effect the transformation. The reaction can be equally run by employing the nitroarene or the diene as limiting agent and works well for nitroarenes bearing either electron-withdrawing or mildly electron-donating substituents. A moderate steric hindrance on the nitroarene (o-methyl) is well tolerated, but 1,4-disubstituted-1,3-dienes are not suitable substrates.
Photoassisted, iron-catalyzed allylic amination of olefins with nitroarenes
Srivastava, Radhey S.,Kolel-Veetil, Manoj,Nicholas, Kenneth M.
, p. 931 - 934 (2007/10/03)
Olefins react with nitroarenes and carbon monoxide photochemically in the presence of [Cp*Fe(CO)2]2 (Cp=η5-C5Me5) to produce N-aryl-N-allyl amines in moderate to good yields. Unsymmetrical olefins react highly regioselectively with N-functionalization at the less substituted vinylic carbon. Mechanistic probes using 2′-nitrobiphenyl, 2,3-dimethylbutadiene and nitrosobenzene suggest that neither aryl nitrenes nor nitrosoarenes are the active aminating agents in these reactions.
Metalation and Alkylation of 3,6-Dihydrothiazine 1-Oxides Prepared via Diels-Alder Cycloadditions of N-Sulfinyl Dienophiles
Bell, Scott I.,Parvez, M.,Weinreb, Steven M.
, p. 373 - 377 (2007/10/02)
The deprotonation of various 3,6-dihydrothiazine 1-oxides using LDA or methyllithium has been investigated.It was found that the stability and chemistry of these lithiated heterocycles are highly dependent upon the nature of the ring nitrogen substituent.Thus, N-alkyldihydrothiazine oxides can be metalated at C-6 to give species postulated as 9, which undergo predominantly anti alkylation with alkyl halides.Alternatively, with MeOD, 9 is deuterated at C-6 primarily in a syn mode.N-Silylated heterocycles ring open rapidly and stereoselectively upon metalation to give dienic sulfinamides like 19, which can be reclosed to the starting dihydrothiazine oxides.N-Phenyl-substituted 3,6-dihydrothiazine 1-oxides upon metalation give mixtures of pyrroles and N-S bond cleavage products.Attempts to generate the dianion from NH dihydrothiazine oxide 17 led only to low yields of C-4 alkylated products with alkyl halides.
