61219-91-8Relevant academic research and scientific papers
Synthesis of α-Chlorolactams by Cyanoborohydride-Mediated Radical Cyclization of Trichloroacetamides
Coussanes, Guilhem,Jakobi, Harald,Lindell, Stephen,Bonjoch, Josep
supporting information, p. 8151 - 8156 (2018/05/30)
A cyanoborohydride-promoted radical cyclization methodology has been developed to access α-chlorolactams in a simple and efficient way using NaBH3CN and trichloroacetamides easily available from allylic and homoallylic secondary amines. This methodology allowed the synthesis of a library of α-chlorolactams (mono- and bicyclic), which were tested for herbicidal activity, trans-3-chloro-4-methyl-1-(3-trifluoromethyl)phenyl-2-pyrrolidinone being the most active.
Radical reactions using decacarbonyldimanganese under biphasic conditions
Huther, Nathalie,McGrail, P. Terry,Parsons, Andrew F.
, p. 1740 - 1749 (2007/10/03)
Radical reactions of alkyl halides, initiated by photolysis in the presence of decacarbonyldimanganese, can be performed in biphasic media. Reactions in the presence of aqueous sodium hydroxide together with a phase-transfer catalyst result in the efficient removal of manganese halide by-products and also lead to the regeneration of decacarbonyldimanganese. A range of efficient radical couplings, cyclisations and intermolecular addition reactions were performed under these conditions. This included the development of a new tandem radical addition-ionic cyclisation sequence that was employed in a short approach to (±)-coronamic acid. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Halogen atom transfer radical cyclization of N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinones, promoted by Fe0-FeCl3 or CuCl-TMEDA
Benedetti, Miriam,Forti, Luca,Ghelfi, Franco,Pagnoni, Ugo Maria,Ronzoni, Roberto
, p. 14031 - 14042 (2007/10/03)
The halogen atom transfer radical cyclization of a N-allyl-N-benzyl-2,2-dihaloamides to 2-pyrrolidinones has been carried out in high yields under mild conditions, in a reaction promoted by CuCl-TMEDA or Fe0-FeCl3 in acetonitrile or N,N-dimethylformamide, respectively.
Transition Metal-Catalyzed Radical Cyclizations: A Low-Temperature Process for the Cyclization of N-Protected N-Allyltrichloroacetamides to Trichlorinated γ-Lactams and Application to the Stereoselective Preparation of β,γ-Disubstituted γ-Lactams
Nagashima, Hideo,Ozaki, Nobuyasu,Ishii, Masayuki,Seki, Koji,Washiyama, Masayoshi,Itoh, Kenji
, p. 464 - 470 (2007/10/02)
Cyclisations of N-substituted N-allyltrichloroacetamides, where the substituent is an alkyl, Cbz, Boc, Ts, or Ms group, are catalyzed by a 1:1 mixture of CuCl and bipyridine to give the corresponding β,γ-trichlorinated γ-lactams in high yields.The reactions proceed at temperatures from -78 deg C to room temperature.Cyclizations of N-allyltrichloroacetamides of acyclic secondary allylic amines are achieved with good selectivity; the cis/trans ratios of the γ-lactams formed were dependent on the substituents on the nitrogen atom.The stereochemical outcome is compared with that of free-radical cyclization.
