51220-12-3Relevant academic research and scientific papers
Synthesis and Reactivity of Aziridines with Internal Dipolarophiles: An Approach to 1,4-Dihydrochromeno[4,3- b ]pyrroles and 3-Methylenechromano[4,3- b ]pyrroles
Ribeiro Laia, Fernanda M.,Pinho e Melo, Teresa M. V. D.
, p. 2781 - 2790 (2015)
Aziridines derived from 2-(prop-2-yn-1-yloxy)- and 2-(buta-2,3-dien-1-yloxy)chalcones and from benzyl 2-(prop-2-yn-1-yloxy)- and 2-(buta-2,3-dien-1-yloxy)phenylacrylates were prepared in a stereoselective fashion. Their reactivity as azomethine ylide precursors was examined, leading to the synthesis of 1,4-dihydrochromeno[4,3-b]pyrrole and 3-methylenechromano[4,3-b]pyrrole derivatives through intramolecular 1,3-dipolar cycloaddition reactions.
General Pyrrolidine Synthesis via Iridium-Catalyzed Reductive Azomethine Ylide Generation from Tertiary Amides and Lactams
Yamazaki, Ken,Gabriel, Pablo,Di Carmine, Graziano,Pedroni, Julia,Farizyan, Mirxan,Hamlin, Trevor A.,Dixon, Darren J.
, p. 7489 - 7497 (2021)
An iridium-catalyzed reductive generation of both stabilized and unstabilized azomethine ylides and their application to functionalized pyrrolidine synthesis via [3 + 2] dipolar cycloaddition reactions is described. Proceeding under mild reaction conditions from both amide and lactam precursors possessing a suitably positioned electron-withdrawing or a trimethylsilyl group, using 1 mol% Vaska's complex [IrCl(CO)(PPh3)2] and tetramethyldisiloxane (TMDS) as a terminal reductant, a broad range of (un)stabilized azomethine ylides were accessible. Subsequent regio- and diastereoselective, inter- and intramolecular dipolar cycloaddition reactions with variously substituted electron-deficient alkenes enabled ready and efficient access to structurally complex pyrrolidine architectures. Density functional theory (DFT) calculations of the dipolar cycloaddition reactions uncovered an intimate balance between asynchronicity and interaction energies of transition structures, which ultimately control the unusual selectivities observed in certain cases.
1,3-Dipolar cycloaddition of azomethine ylides generated from aziridines in supercritical carbon dioxide
Gomes, Paulo J.S.,Nunes, Cláudio M.,Pais, Alberto A.C.C.,Pinho e Melo, Teresa M.V.D.,Arnaut, Luis G.
, p. 5475 - 5479 (2006)
The 1,3-dipolar cycloaddition of azomethine ylides with DMAD in supercritical carbon dioxide is reported. The photolysis reaction conditions were optimized with a suitable adjustment of pressure, temperature, irradiation time and co-solvent concentration
Phospha-Muenchnones: Electronic structures and 1,3-dipolar cycloadditions
St-Cyr, Daniel J.,Morin, Marie S. T.,Belanger-Gariepy, Francine,Arndtsen, Bruce A.,Krenske, Elizabeth H.,Houk
experimental part, p. 4261 - 4273 (2010/08/06)
The reaction of imines, acid chlorides, PR3, and base generates a new class of 1,3-dipoles: phospha-Muenchnones. These 1,3-dipoles can undergo cycloadditions with alkynes followed by loss of phosphine oxides to form pyrroles. Cycloaddition reac
A new use of wittig-type reagents as 1,3-dipolar cycloaddition precursors and in pyrrole synthesis
St. Cyr, Daniel J.,Arndtsen, Bruce A.
, p. 12366 - 12367 (2008/03/30)
The one-pot reaction of imines, acid chlorides, and phosphonites has been found to generate a new class of phosphorus-based 1,3-dipolar cycloaddition reagent. These substrates, which are isomeric forms of classic Wittig reagents, undergo cycloaddition rea
Generation of Azomethine Ylides via the Desilylation Reaction of Immonium Salts
Padwa, Albert,Haffmanns, Gunter,Tomas, Miguel
, p. 3314 - 3322 (2007/10/02)
Generation of intermediates having azomethine ylide reactivity was achieved by the reaction of several ethanol or thioimidate derivatives with methyl iodide followed by treatment of the resulting imine with (trimethylsilyl)methyl triflate.Desilylation of
Addition de cyano-2 aziridines a quelques alcynes; obtention de pyrroles
Merah, Boumediene,Texier, Fernand
, p. 552 - 558 (2007/10/02)
Addition of the α-bromocinnamonitrile to primary amines (Cromwell method) leads to 2-cyano-3-phenyl-N-alkyl-aziridines, but the formation of the isomeric enamines always competes with this reaction.These aziridines, which are potential azomethine-ylids, a
