One-Pot Synthesis of Succinimide-3-Carboxamide Derivatives Using Microwave and Mechanistic insights and Kinetics analysis by Computational Method

  • سال انتشار: 1398
  • محل انتشار: بیست و هفتمین کنفرانس شیمی آلی ایران
  • کد COI اختصاصی: ISOC27_197
  • زبان مقاله: انگلیسی
  • تعداد مشاهده: 238
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نویسندگان

Zohreh Shirdel

Department of Chemistry, Faculty of Science, Zahedan Branch Islamic Azad University, Zahedan, Iran

Seyyed Mohammad Reza Hosseini-Tabatabaei

Department of Chemistry, Faculty of Science, Zahedan Branch Islamic Azad University, Zahedan, Iran

Mohammad Amin Kazemian

Department of Chemistry, Faculty of Science, Zahedan Branch Islamic Azad University, Zahedan, Iran

چکیده

In the present work, one-pot and four-component condensation of Meldrum’s acid(1) and acetone(2) with tert-butyl isocyanides(3) in the presence of primary amines(4) under microwave irradiation which provided 1-tert-butyl-4,4-dimethyl-2,5-dioxopyrrolidine-3-carboxamides(5) in short time with high yields have been investigated. Also, multiple mechanisms have been studied theoretically for comparing formation of the amidosuccinimide with triamide products from intermediate 9 using ab initio molecular orbital theory in gas phase. The potential energy profile was constructed at the HF/6-311G (d, p) level of theory. Among four speculative proposed path only the pathway A (intramolecular reaction to formation amidosuccinimide product) was recognized as a desirable mechanism. Theoretical kinetics data involving k and activation parametres (Ea , ΔG‡, ΔS‡ and ΔH‡) were calculated for each step of the paths. In order to determine the possible nucleophilic sites for the N17, N33 local reactivity has been evaluated through Fukui indices.

کلیدواژه ها

Meldrum’s acid, tert-butyl isocyanides, Mechanism, Theoretical and kinetics investigation, microwave irradiation, Two dimensional scanning, Amidosuccinimides

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