33812-87-2Relevant academic research and scientific papers
The stereoselective synthesis of alkenyl-β-lactams by palladium-catalyzed [2+2] carbonylative cycloaddition
Troisi, Luigino,De Vitis, Luisella,Granito, Catia,Epifani, Erbana
, p. 1357 - 1362 (2004)
Allyl halides of different structures, under CO pressure, in the presence of Et3N, a catalytic amount of Pd(OAc)2, and triphenylphosphane as ligand, undergo a [2+2] cycloaddition reaction with various imines. The reaction is highly regio- and stereoselective: β-lactams are formed in good yields and with trans diastereoselectivity in both the β-lactam ring and the vinylic moiety. New and important information is suggested regarding the known reaction mechanism. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Triflic acid promoted fries rearrangement of C-3 vinyl/isopropenyl-azetidin-2-ones: Single-pot synthesis of C-3 functionalized-2-aryl-2,3-dihydro-quinoline-4(1H)-ones
Mehra, Vishu,Singh, Parvesh,Bisetty, Krishna,Kumar, Vipan
, p. 41793 - 41801 (2014)
The β-lactam-synthon-interceded synthesis of C-3 functionalized 2-aryl-2,3-dihydro-quinoline-4(1H)-ones has been described via the Fries rearrangement of C-3 vinyl/isopropenyl substituted β-lactams. The reaction at 0 °C resulted in the isolation of a tautomeric mixture, and the preferential formation of the conjugated product was observed at higher temperatures. Density functional theory (DFT) calculations and molecular dynamics (MD) simulations were additionally performed to explain the preferential formation of product 2 over 3. The proposed mechanism was further validated via the base-induced isomerisation of the mixture of 2a and 3a. This journal is
Diastereoselective synthesis of 2,3-disubstituted 1-arylazetidines via NaBH4-promoted facile reduction of C-3 functionalized azetidin-2-ones
Mehra, Vishu,Neetu,Kumar, Vipan
, p. 4763 - 4766 (2013/08/23)
A facile diastereoselective synthesis of 2,3-disubstituted 1-arylazetidines has been reported via NaBH4-promoted reduction of C-3 functionalized azetidin-2-ones. Since the developed protocol does not involve the use of a Lewis acid, the methodo
The synthesis of β-lactams via a one-pot Reformatsky reaction of imines promoted by Zn/Cp2TiCl2 (cat.)
Chen, Lei,Zhao, Gang,Ding, Yu
, p. 2611 - 2614 (2007/10/03)
In the presence of Zn/Cp2TiCl2 (cat.) α-bromoacetates, γ-bromocrotonates or α-bromomethylacrylates react with imines in one-pot to form β-lactams, 3-vinyl-β-lactams or α-methylene-γ-lactams, respectively, at room temperature without
Microwave-assisted rapid and simplified hydrogenation
Banik, Bimal K.,Barakat, Khaled J.,Wagle, Dilip R.,Manhas, Maghar S.,Bose, Ajay K.
, p. 5746 - 5753 (2007/10/03)
Catalytic transfer hydrogenation has been conducted under microwave irradiation in open vessels using high-boiling solvents such as ethylene glycol (bp 198 °C) as the microwave energy transfer agent. Reduction of double bonds and hydrogenolysis of several functional groups were carried out safely and rapidly (3-5 min) at about 110-130 °C with 10% Pd/C as an efficient catalyst and ammonium formate as the hydrogen donor. Diverse types of β-lactam synthons were prepared by the reduction of ring substituents containing alkene and alkylidene groups or conjugated unsaturated esters. Cleavage of the β-lactam ring by hydrogenolysis of the N-C4 bond of 4- aryl-2-azetidinones was a facile reaction with 10% Pd/C as the catalyst; but no ring scission occurred when Raney nickel catalyst was employed. Dehalogenation of aromatic compounds was also successful with ammonium formate and Pd/C catalyst. Hydrogenolysis of phenylhydrazone of methyl benzoylformate gave the methyl ester of phenylglycine in excellent yield. The techniques described here for microwave assisted hydrogenation are safe, rapid, and efficient and are suitable for research investigation as well as for undergraduate and high school laboratory exercises.
A NOVEL CHEMICAL TRANSFORMATION OF 3-VINYL-4-SUBSTITUTED-2-AZETIDINONES
Bose, Ajay K.,Krishnan, Lalitha,Wagle, Dilip R.,Manhas, Maghar S.
, p. 5955 - 5958 (2007/10/02)
Transformation of α-vinyl-β-lactams involving an anti-Markovnikov addition reaction is described.The action of PdCl2-CuCl-O2 on the vinyl group leads to terminal aldehydes instead of the expected methyl ketones.The intermediate prepa
