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

سال انتشار: 1398
نوع سند: مقاله کنفرانسی
زبان: انگلیسی
مشاهده: 154

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شناسه ملی سند علمی:

ISOC27_197

تاریخ نمایه سازی: 19 اسفند 1399

چکیده مقاله:

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.

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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