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Sonocatalyzed Total Synthesis of N,N-diaryl-formamides Through Oxidation and Hydrolysis Reaction of gem-dichloroaziridines using DMSO/H2O

[ Vol. 15 , Issue. 7 ]

Author(s):

Khadijeh Rabiei* and Hossein Naeimi   Pages 1014 - 1019 ( 6 )

Abstract:


Background: Aziridine compounds are among the most fascinating intermediates in organic synthesis, acting as precursors of many complex molecules due to the strain incorporated in their skeletons and can be opened in a stereo controlled manner with various nucleophiles, providing access to a wide range of important nitrogen-containing products. Sonochemistry involves the use of ultrasound technique to promote organic reactions. In recent years sonochemistry has been widely used in organic syntheses as it offers a versatile and facile pathway for a bewildering range of organic reactions.

Material and Method: The synthesis of some Schiff bases was done in according the previously reported procedure in literature. The synthesized Schiff bases in the presence of magnesium powder and CCl4 in anhydrous tetrahydrofuran was converted to gem-dichloroaziridines at ultrasonic irradiation. Finally, the synthesized 2,2- dichloro-1,3-bis(4-chlorophenyl) aziridine was treated with DMSO and H2O with ultrasonic irradiation to produce the N-(4-chlorophenyl)-N-[4-(chlorophenyl)hydroxy-methyl] formamides.

Results: Here, total synthesis of N-(α-hydroxybenzyl)-formamides through ultrasonic promoted oxidation and hydrolysis reaction of gem-dichloroaziridine derivatives in the presence of dimethyl sulfoxide and water has been investigated.

Conclusion: In this study, ultrasonic promoted oxidation and hydrolysis of gem-dichloroaziridines toward N- (α-hydroxybenzyl)-formamides in the presence of DMSO and H2O under neutral medium reaction conditions has been reported. Excellent yields of products were obtained through this method. Other advantages of this reaction are short reaction times, simplicity of the method and high purity of products.

Keywords:

Dichloroaziridine, DMSO, formamide, oxidation, schiff base, synthesis, ultrasonic.

Affiliation:

Department of Chemistry, Faculty of Basic Science, Qom University of Technology, Qom 37195, Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, 87317

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