95628-94-7Relevant academic research and scientific papers
Aluminum-Catalyzed Formation of Functional 1,3,2-Dioxathiolane 2-Oxides from Sulfur Dioxide: An Easy Entry towards N-Substituted Aziridines
Laserna, Victor,Martin, Eddy,Escudero-Adán, Eduardo C.,Kleij, Arjan W.
, p. 3832 - 3839 (2016/12/16)
Aluminum(III) complexes derived from aminotriphenolate ligands are shown to be excellent catalysts for the formation of cyclic sulfites from a range of (functionalized) terminal and internal epoxides, and ex situ generated sulfur dioxide. The developed catalytic protocol is characterized by its operational simplicity, wide scope in epoxide reaction partners, good to excellent isolated yields and mild reaction conditions [50–70 °C, p(SO2) a three-step protocol. (Figure presented.).
One-pot synthesis of aziridines from vinyl selenones and variously functionalized primary amines
Sternativo, Silvia,Marini, Francesca,Del Verme, Francesca,Calandriello, Antonella,Testaferri, Lorenzo,Tiecco, Marcello
experimental part, p. 6851 - 6857 (2010/09/18)
Variously substituted aziridines were conveniently prepared by an aza-Michael Initiated Ring Closure (aza-MIRC) reaction starting from vinyl selenones and primary amines, aminoalcohols or diamines. The reactions proceed in very high yields at room temperature in toluene or water. A significant rate acceleration was observed under aqueous conditions.
Routes to Mitomycins. Chirospecific Synthesis of Aziridinomitosenes
Shaw, Kenneth J.,Luly, Jay R.,Rapoport, Henry
, p. 4515 - 4523 (2007/10/02)
The syntheses of ethyl (1R,2R)-1,2-(N-benzylaziridino)-7-methoxy-6-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrroloindole-9-carboxylate (59) and a regioisomeric aziridinoindoloquinone 60 are presented.Aziridine ring closure on a tricyclic indoloquinone nucleus and on monocyclic pyrrolidine derivatives was unsuccessful but did succeed with the acyclic educt.Thus the synthesis of the target aziridinomitosene was achieved by aziridine ring closure on the asymmetric 2-amino-3-hydroxy-4-azidobutanoate 49 followed by homologation and reductive ring closure to the bicyclic aziridinopyrrolidine 54.Subsequent reduction, regiospecific addition to 2,3-dibromo-5-methoxy-6-methylbenzoquinone (27), photochemical rearrangement, oxidation, and palladium-catalyzed ring closure afforded the (R,R)-aziridinomitosene 59.Regioisomeric aziridinoindoloquinone 60 was obtained directly by the addition of bicyclic aziridine 54 to dibromoquinone 27 followed by copper(II)-catalyzed ring closure.
