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Shaabani A, Hooshmand SE. Diversity-oriented catalyst-free synthesis of pseudopeptides containing rhodanine scaffolds via a one-pot sequential isocyanide-based six-component reactions in water using ultrasound irradiation. Ultrason Sonochem. 2017;40:84-90doi: 10.1016/j.ultsonch.2017.06.030.
Shaabani, A., & Hooshmand, S. E. (2018). Diversity-oriented catalyst-free synthesis of pseudopeptides containing rhodanine scaffolds via a one-pot sequential isocyanide-based six-component reactions in water using ultrasound irradiation. Ultrasonics sonochemistry, 4084-90. https://doi.org/10.1016/j.ultsonch.2017.06.030
Shaabani, Ahmad, and Hooshmand, Seyyed Emad. "Diversity-oriented catalyst-free synthesis of pseudopeptides containing rhodanine scaffolds via a one-pot sequential isocyanide-based six-component reactions in water using ultrasound irradiation." Ultrasonics sonochemistry vol. 40 (2018): 84-90. doi: https://doi.org/10.1016/j.ultsonch.2017.06.030
Shaabani A, Hooshmand SE. Diversity-oriented catalyst-free synthesis of pseudopeptides containing rhodanine scaffolds via a one-pot sequential isocyanide-based six-component reactions in water using ultrasound irradiation. Ultrason Sonochem. 2018 Jan;40:84-90. doi: 10.1016/j.ultsonch.2017.06.030. Epub 2017 Jun 30. PMID: 28946494.
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Ultrason Sonochem. 2018 Jan;40:84-90. doi: 10.1016/j.ultsonch.2017.06.030. Epub 2017 Jun 30.

Diversity-oriented catalyst-free synthesis of pseudopeptides containing rhodanine scaffolds via a one-pot sequential isocyanide-based six-component reactions in water using ultrasound irradiation.

Ultrasonics sonochemistry

Ahmad Shaabani, Seyyed Emad Hooshmand

Affiliations

  1. Faculty of Chemistry, Shahid Beheshti University, G. C., P.O. Box 19396-4716, Tehran, Iran. Electronic address: [email protected].
  2. Faculty of Chemistry, Shahid Beheshti University, G. C., P.O. Box 19396-4716, Tehran, Iran.

PMID: 28946494 DOI: 10.1016/j.ultsonch.2017.06.030

Abstract

A planning strategy for diversity-oriented catalyst-free synthesis of pseudopeptides containing rhodanine scaffolds has been developed via a novel one-pot sequential six-component reaction in water. This approach is an efficient, environmentally friendly and expeditious procedure for direct access to wide ranges of pharmacologically significant and structurally interesting compounds based on the union of multicomponent reactions approach via tandem Michael/domino cycloaddition/Ugi reactions sequence from readily available starting materials. The syntheses were achieved by reaction of various primary amines, carbon disulfide, maleic anhydride or itaconic anhydride, aromatic aldehydes, anilines and isocyanides under ultrasound irradiation at room temperature in good yields. Providing of pseudopeptides containing rhodanines with the tandem formation of one new heterocyclic ring as well as creating the seven new bonds such as carbon-carbon, carbon-nitrogen, carbon-oxygen and carbon-sulfur with great efficiency and high atom/bond-forming/structure economy are outstanding features of this designed synthetic route.

Copyright © 2017 Elsevier B.V. All rights reserved.

Keywords: Catalyst-free reaction; Isocyanides; Pseudopeptides; Rhodanines; Ultrasonic irradiation; Union of MCRs

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