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Facile, capable, atom-economical one-pot multicomponent strategy for the direct regioselective synthesis of novel isoxazolo[5,4-d]pyrimidines

  • Mehdi RimazEmail author
  • Hossein Mousavi
  • Leila Ozzar
  • Behzad Khalili
Article
  • 13 Downloads

Abstract

Facile and efficient NaOH-promoted one-pot regioselective synthesis of 5,7-dimethyl-3-(arylamino)isoxazolo[5,4-d]pyrimidine-4,6(5H,7H)-diones and 5,7-dimethyl-3-(arylamino)-6-thioxo-6,7-dihydroisoxazolo[5,4-d]pyrimidin-4(5H)-ones as pharmaceutically interesting compounds has been developed based on a three-component reaction between aryl isothiocyanates, N,N-dimethylbarbituric acid or N,N-dimethyl-2-thiobarbituric acid, and hydroxylamine hydrochloride in N,N-dimethylformamide (DMF) at room temperature. This new protocol has advantages such as simple operation, regioselectivity, metal-free operation, high atom economy, moderate to high yield, easy work-up procedure, and applicability on the gram scale.

Graphical abstract

Keywords

Isoxazolopyrimidine Aryl isothiocyanate One-pot Hydroxylamine Gram scale 

Notes

Acknowledgements

We are grateful for financial support from the Research Council of Payame Noor University.

Compliance with ethical standards

Conflict of interest

The authors declare no conflicts of interest.

Supplementary material

11164_2019_3757_MOESM1_ESM.doc (28.6 mb)
Supplementary material 1 (DOC 29261 kb)

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© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of ChemistryPayame Noor UniversityTehranIran
  2. 2.Department of Organic Chemistry, Faculty of ChemistryUrmia UniversityUrmiaIran
  3. 3.Department of Chemistry, Faculty of SciencesUniversity of GuilanRashtIran

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