2770-15-2Relevant academic research and scientific papers
Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions
Joseph, Devaneyan,Lee, Sunwoo,Park, Myeong Seong
supporting information, p. 6227 - 6232 (2021/07/28)
N-Acyl lactam amides, such as benzoylpyrrolidin-2-one, benzoylpiperidin-2-one, and benzoylazepan-2-one reacted with amines in the presence of DTBP and TBAI to afford the transamidated products in good yields. The reactions were conducted under aqueous conditions and good functional group tolerance was achieved. Both aliphatic and aromatic primary amines displayed good activity under metal-free conditions. A radical reaction pathway is proposed.
Novel aryl ether derivatives as antiinflammatory and analgesics
Rashmi,Rao, Gopal Krishna,Devi, Kshama,Shivananda,Swetha,Ga, Suneetha
, p. 1401 - 1407 (2012/06/29)
The diaryl ether moieties have attracted considerable attention of medicinal chemists as they are endowed with a wide range of diverse biological activities. The present study involves synthesis, characterization of some new aryl ethers and evaluation of their antiinflammatory and analgesic activity. A series of new aryl ether derivatives [4(a-h), 5] were prepared by Ullmann's ether condensation. The structures of new compounds are supported by their IR, 1H NMR and Mass spectra. The new derivatives were evaluated for their antiinflammatory and analgesic activity. Among the tested, compound 3 has shown better antiinflammatory and analgesic activity.
Synthesis and enantioselective hydrogenation of seven-membered cyclic imines: Substituted dibenzo[b,f][1,4]oxazepines
Gao, Kai,Yu, Chang-Bin,Li, Wei,Zhou, Yong-Gui,Zhang, Xumu
, p. 7845 - 7847 (2011/09/13)
Highly enantioselective hydrogenation of seven-membered cyclic imines, substituted dibenzo[b,f][1,4]oxazepines, was achieved, with up to 94% ee, by using the [Ir(COD)Cl]2/(S)-Xyl-C3*-TunePhos complex as the catalyst in the presence of morpholine-HCl.
Peroxydicarbonate-mediated oxidation of N-(ortho-aryloxyphenyl) and N-(ortho-arylaminophenyl)aldimines
Leardini, Rino,McNab, Hamish,Nanni, Daniele
, p. 12143 - 12158 (2007/10/02)
Imidoyl radicals 5, obtained from imines 1 by hydrogen abstraction with di-iso-propyl peroxydicarbonate (DPDC), give dibenzoxazepines through 7-membered ring closure. A competitive 6-membered cyclisation leads to intermediate spirocyclohexadienyl radicals that rearrange to aryloxy radicals; this process entails a novel 1,5-aryl radical translocation from an oxygen to a carbon atom and leads to benzophenones, benzoxazoles, and biphenyls. The possibility that the oxazepines arise from rearrangement of the 6-membered-ring-closure intermediates is discussed. With imine 1e, the formation of 5e occurs to a minor extent owing to a side-reaction of the iso-propoxycarbonyloxy radicals, which give rise to an intermolecular aromatic ipso-substitution on the benzenic ring linked to the two oxygen atoms. The 1,5-aryl migration can also be observed with imidoyl radicals generated by radical addition to 2-phenoxyisocyanobenzene. In contrast, the reactions of imines 2 with DPDC do not afford imidoyl radicals, as abstraction of the iminic hydrogen is slower than oxidation of the methyl group: this process entails the formation of carbamoyl radicals, which cyclise onto the carbonitrogen double bond, furnishing quinoxalinone derivatives, or loose carbon monoxide to yield benzimidazoles through ring closure of aminyl radicals. A novel cyclisation of a nitrogen-centred radical onto a formamido group could account for the formation of a benzimidazolinone derivative.
N-(ortho-Aryloxyphenyl)arylimidoyl Radicals: Novel 1,5-Aryl Radical Translocation from Oxygen to Carbon
Guidotti, Simona,Leardini, Rino,Nanni, Daniele,Pareschi, Patrizia,Zanardi, Giuseppe
, p. 451 - 454 (2007/10/02)
Imidoyl radicals 4a-d, obtained by hydrogen abstraction from imines 1a-d, give 7-membered cyclisation leading to oxazapines 2a-d.The intermediate spirocyclohexadienyl radicals of the competitive 6-membered ring closure (6a-d) rearrange to aryloxy radicals , giving benzophenones 3a-d: the whole process entails a novel 1,5-aryl radical translocation from an oxygen to a carbon atom.
