1,3-Dipolar Cycloaddition Reactions on Medicine Dimethisterone: A Computational Insight
Publish place: 26th Iranian Seminar on Organic Chemistry
Publish Year: 1397
نوع سند: مقاله کنفرانسی
زبان: English
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شناسه ملی سند علمی:
ISOC26_162
تاریخ نمایه سازی: 2 شهریور 1398
Abstract:
The different types of 1,3-dipolar cycloaddition (1,3-DC) reactions have been widely used invarious fields. Based on the recent researches, stereochemistry of these reactions is spotlight[1]. In this study, the theoretical aspects of the electrostatic attraction effect on the regioselectivityof the 1,3-DC reactions to dimethisterone was assessed which it is a progestin medication[2] as a dipolarophile white nitrile imine (a), nitrile oxide (b) and azide (d) as 1,3-dipoles.Cycloaddition of dimethisterone to each of a-d can lead to regioselective five-membered heteroaromaticrings, the 4- and/or 5-substituted, due to secondary effect between the hetro atomof 1,3-dipoles and the hydroxy group in dimethisterone. These heteroaromatic rings werewidely used as an important role in various biochemical processes [3]. In this study, the (1,3-DC) reaction of dimethisterone with a-d were utilized to produce the five-membered aromaticheterocyclic rings, i.e. pyrazole, isoxazole and triazole derivatives. Data were calculated andobtained by DFT-B3LYP/6-31G* method.
Authors
Marzieh Hashemi
Department of Organic Chemistry, Faculty of Chemistry, ۱ Razi University, Kermanshah, Iran
Avat(Arman) Taherpour
Department of Organic Chemistry, Faculty of Chemistry, ۱ Razi University, Kermanshah, Iran- Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran