24290-58-2Relevant academic research and scientific papers
Regio-controlled and stereo-controlled ring expansion of N-substituted-2 benzoylaziridines using Fe(NO3)3
Samimi, Heshmat A.,Shams, Zahra
, p. 1659 - 1663 (2014)
Several N-acyl-2-benzoylaziridines were previously prepared conveniently and used in the preparation of 5-benzoyl-2,4-diaryl oxazolines in the presence of NaI. In this work, synthesis of some trans-4-benzoyl- 2,5-diaryl oxazolines by a regio-controlled an
K5[PW11ZnO39].23H2O-catalyzed acylation/ring expansion of ketoaziridines in a single pot: A new regio- and stereo-selective route for the synthesis of oxazolines
Samimi, Heshmat A.,Mostafavi, Akram,Farsani, Mostafa Riahi
, p. 2031 - 2035 (2015)
A new and one-pot synthesis of oxazolines has been accomplished by K5[PW11ZnO39].23H2O - catalyst acylation followed by C-N ring opening/C-O bond formation in NH ketoaziridines. This regio- and stereo-selective reaction presumably proceeds via a domino sequence resulting in the in situ generation of acyl aziridine which undergoes a ring expansion reaction via an initial C-N rupture of aziridine ring followed by ring closure to the oxazolines. The methodology provided novel one-pot procedure for the synthesis of trans-2,5-diaryl-4-aroyloxazolines.
Fe(NO3)3 as an efficient catalyst for regio- and stereo-controlled ring expansion of 1,2-diaroyl-3-arylaziridines
Samimi, Heshmat A.,Shams, Zahra
, p. 979 - 984 (2014)
Several 1,2-diaroyl-3-arylaziridines were previously prepared conveniently and used in the preparation of 5-benzoyl-2,4-diaryl oxazolines in the presence of NaI. In this work, synthesis of some trans-4-benzoyl-2,5-diaryl oxazolines by a regio- and stereo-controlled reaction in the presence of Iron (III) nitrate at room temperature is reported. A plausible mechanism has been proposed for ring expansion of N-acyl aziridines to oxazolines.
Regio- and stereo-controlled isomerization of 1,2-diaroyl-3-aryl aziridines to the corresponding N-((Z)-1-oxo-1,3-diphenylprop-2-en-2-yl) benzamide
Samimi, Heshmat A.,Yamin, Bohari M.,Soltani, Marzieh
, p. 1467 - 1472 (2014/10/16)
Regio- and stereo-controlled isomerization of 1,2-diaroyl-3-aryl aziridines to the corresponding N-((Z)-1-oxo-1,3-diphenylprop-2-en-2-yl) benzamide in the presence of diethyl thiourea in room temperature is described. A plausible mechanism has been proposed. The structures of the products were confirmed by X-ray analysis.
An efficient synthesis of 5-benzoyloxazolines by regio- and stereo-controlled reaction of N-substituted 2-benzoylaziridines under microwave irradiation
Samimi, Heshmat A.,Mamaghani, Manouchehr,Tabatabaeian, Khalil
experimental part, p. 1765 - 1770 (2009/05/31)
(Chemical Equation Presented) Several N-acyl-2-benzoylaziridines were prepared conveniently in good to high yields (71-93%) and used in the preparation of 5-benzoyloxazolines (76-91%) by a regio- and stereo-controlled reaction in the presence of NaI as an
ONE STEP SYNTHESIS OF AZIRIDINES BY THE MICHAEL TYPE ADDITION OF FREE SULFIMIDES
Furukawa, Naomichi,Yoshimura, Toshiaki,Ohtsu, Masami,Akasaka, Takeshi,Oae, Shigeru
, p. 73 - 80 (2007/10/02)
The Michael type additions of diphenyl N-unsubstituted sulfimide (free sulfimide) to various electrophilic olefins were carried out.The reaction with cis- and trans-dibenzoylethylene, dimethylfumarate, dimethylmaleate, benzalacetophenone and benzalacetone gave mainly the corresponding trans-2-acylaziridines and trans-enaminoketones.However, phenyl vinyl sulfone or acrylonitrile afforded not the corresponding aziridine but diphenyl-N-2-cyano or N-2-phenylsulfonylethylsulfimide, a simple Michael adduct.When optically active (+)-(R)-o-methoxyphenylphenyl free sulfimide was treated with such an α,β-unsaturated carbonyl compound as benzalacetophenone, an optically active 2-acylaziridine, i.e., (-)-trans-2-benzoyl-3-phenylaziridine was obtained in ca 30percent optical purity and its absolute configuration was assigned as (2R,3S) upon chemical transformation to the configurationally known 2-phenyl-2-benzoylamino-1-ethanol or by comparing its CD spectrum with that of (1R,2R)-1-phenyl-2-benzoyl-cyclopropane.Meanwhile, (-)-(S)-o-methoxyphenylphenyl free sulfimide was found to react with benzalacetophenone to afford (+)-trans-2-benzoyl-3-phenylaziridine of 25percent optical purity.Effects of solvent and temperature on both the distribution of the products ratio and the optical yield were examined.
