54520-84-2Relevant academic research and scientific papers
Synthesis of γ-lactams via Ru(II)–Pheox-catalyzed regioselective intramolecular Csp3–H insertion of diazoacetamides
Fujii, Takuji,Thu, Huong Dang Thi,Iwasa, Seiji
, (2020/08/19)
Herein, γ-lactam derivatives are obtained in high yield via highly regioselective intramolecular Csp3–H insertion reactions of α-diazoacetamides catalyzed by a rac-Ru(II)–Pheox complex. The catalytic system is applicable to a wide range of diaz
Substituted 1-methyl-4-phenylpyrrolidin-2-ones – Fragment-based design of N-methylpyrrolidone-derived bromodomain inhibitors
Hilton-Proctor, J. P.,Ilyichova, O.,Jennings, I. G.,Johnstone, R. W.,Mountford, S. J.,Scanlon, M. J.,Shortt, J.,Thompson, P. E.,Zheng, Z.
, (2020/03/03)
N-Methylpyrrolidone is one of several chemotypes that have been described as a mimetic of acetyl-lysine in the development of bromodomain inhibitors. In this paper, we describe the synthesis of a 4-phenyl substituted analogue – 1-methyl-4-phenylpyrrolidin-2-one – and the use of aryl substitution reactions as a divergent route for derivatives. Ultimately, this has led to structurally complex, chiral compounds with progressively improved affinity as inhibitors of bromodomain-containing protein 4.
Cyclisation at very high temperature. Thermal transformations of N-alkyl and N, N-dialkyl amides of α,β-unsaturated acids into mono- and bicyclic heterocycles under FVT conditions
Le?niak, Stanis?aw,Nazarski, Ryszard B.,Pasternak, Beata
experimental part, p. 6364 - 6369 (2009/12/04)
Cyclisations of N-alkyl and N,N-dialkyl cinnamic amides to the corresponding pyrrolidin-2-ones under the conditions of flash vacuum thermolysis (FVT), are described. It was found that these reactions proceed at 950-1000 °C affording in various yields the
Aryl pyrrolidinones via radical 1,4-aryl migration and 5-endo-trig cyclisation of N-(2-bromoallyl)arylcarboxamides
Palframan, Matthew J.,Tchabanenko, Kirill,Robertson, Jeremy
, p. 8423 - 8425 (2007/10/03)
Radical reaction of a series of N-(2-bromoallyl)arylcarboxamides led to the production of 4-arylpyrrolidin-2-ones and directly reduced materials in comparable yields. A cascade process, involving sequential 5-exo-trig spirocyclisation, β-scission, and 5-endo-trig cyclisation of the resulting acyl radical, is proposed to explain the pyrrolidinone products.
Cyclisation at very high temperature. Thermal transformations of N-alkyl and N,N-dialkyl cinnamic amides into pyrrolidin-2-ones under FVT conditions
Le?niak, Stanis?aw,Pasternak, Beata
, p. 3093 - 3095 (2007/10/03)
Novel cyclisations of N-alkyl and N,N-dialkyl cinnamic amides to the corresponding pyrrolidin-2-ones under the conditions of flash vacuum thermolysis, are described. It was found that this reaction proceeds at 950-1000°C affording a mixture of isomeric pyrrolidin-2-ones in various yields. Two possible mechanisms are proposed for the process.
Synthesis of pyrrolidin-2-ones by 5-endo-trigonal radical cyclisation of N-vinyl-2,2-bis(phenylsulfanyl)acetamides
sato, Tatsunori,Chono, Noriko,Ishibashi, Hiroyuki,Ikeda, Masazumi
, p. 1115 - 1120 (2007/10/02)
A series of N-methyl-N-(1-substituted or 1,2-disubstituted vinyl)-2,2-bis(phenylsulfanyl)acetamides, upon treatment with tributyltin hydride in the presence of a catalytic amount of AIBN in boiling toluene, underwent smooth cyclisation in a 5-endo-trig ma
N-(DIMETHYLALKOXYSILYLMETHYL)- AND N-(DIMETHYLARYLOXYSILYLMETHYL)LACTAMS
Artamkina, O. B.,Kramarova, E. P.,Shipov, A. G.,Baukov, Yu. I.,Macharashvili, A. A.,et al.
, p. 1590 - 1597 (2007/10/02)
A comparison is made of conditions and preparative possibilities of synthesizing Si-substituted N-(dimethylsilylmethyl)lactams with oxygen-containing substituents (alkoxides, aryloxides, benzoates, and triflates) by several methods: by reactions of N-(dimethylchlorosilylmethyl)lactams with sodium alkoxides and with alcohols in the presence of triethylamine, by exchange reactions with trimethylsilyl derivatives of alcohols, phenols, benzoic and trifluoromethylsulfonic acids, and also by a one-pot technique using lactam, dimethylchloromethylchlorosilane, and triethylamine with subsequent addition to the reaction mixture of the alcohol and triethylamine. In the reaction of N-(dimethylchlorosilylmethyl)lactams with sodium alkoxides, concurrently with the replacement of halogen by an alkoxy group the Si-C bond is split to form N-methyllactams, which can also be prepared by the reaction of the initial chlorides with potassium hydroxide. According to IR spectroscopy, intramolecular O->Si coordination is observed in aryloxy-, benzoyloxy-, and trifluoromethylsulfonyloxy derivatives of N-(dimethylsilylmethyl)lactams, whereas the corresponding alkoxy derivatives lack this interaction. The structure of 1-(dimethylsilylmethyl)-2-pyrrolidone phenoxide and benzoate, 1-(dimethylpentafluorophenoxysilylmethyl)perhydro-2-azepinone, and 1-(dimethyltrifluoromethylsulfonyloxymethyl)-2-piperidone was studied by x-ray structural analysis. The lengths of the axial (C=)O->Si and Si-O bonds are, respectively, 2.367 and 1.711(2) Angstroem for the first, 2.228 and 1.711(2) Angstroem for the second, 2.078 and 1.787(2) Angstroem for the third, and 1.753 and 2.785(2) Angstroem for the fourth compound. Variations in the bond lengths are due to the properties of the Si-substituent and to the size of the lactam rings. The ease of formation of the Si-substituted N-(dimethylsilylmethyl)lactams with oxygen-containing substituents via the exchange reaction of N-(dimethylchloromethyl)lactams with the corresponding trimethylsiloxy derivatives correlates with the strength of the silicon-oxygen coordination in the reaction products.
SYNTHESIS AND PROPERTIES OF α-SILYLATED 2-PYRROLIDONE DERIVATIVES
Kramarova, E. P.,Anisomova, N. A.,Baukov, Yu. I.
, p. 1284 - 1290 (2007/10/02)
A method has been described for the synthesis of previously unreported α-silylated N-substituted 2-pyrrolidone derivatives and a study was carried out on the reactions of these compounds with lithium aluminium hydride and electrophilic reagents.
2-Imino-pyrrolidines, process for their preparation, and therapeutic compositions containing same
-
, (2008/06/13)
This invention relates to therapeutically useful compounds, particularly in the cardiovascular field, having the formula: STR1
