Caesium carbonate as a highly efficient catalyst for the synthesis of macrocyclic diamides

Authors

  • Akram Khodadadi Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran
  • Ay Soda Ghobadpoor Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran
  • Esmael Rostami Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran
  • Fatemeh Dehghani Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran
  • Fatemeh Tavazo Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran
  • Mahmood Feraidooni Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran
  • Maryam Bagherzadeh Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran
  • Zahra Abshirini Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran
  • Zahra Heidari Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran
  • Zahra Keshvarz Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Iran
Abstract:

In this research work, we report the synthesis of macrocyclic diamides from the reaction of diesters and aliphatic diamines in the presence of caesium carbonate. It has been demonstrated that among the carbonate of alkali metals (Li2CO3, Na2CO3, K2CO3 and CS2CO3), CS2CO3 appear to be the best catalyst for macrocyclization. Diesters with different substitution patterns on the aromatic ring reacted smoothly with diamines under optimal conditions, affording the corresponding macrocycles in high yields. Introducing a rigid group (e.g., sulfone) on the substrate led to somewhat decreased yield. Various substrates proved to be suitable for this macrocyclization reaction, especially, the flexible ones.

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Journal title

volume 2  issue Issue 3, pp. 162-231

pages  187- 195

publication date 2014-05-01

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