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New one-pot synthesis of spiro[furo[2,3-d]pyrimidine-6,5′-pyrimidine]pentaones and their sulfur analogues

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Abstract

Reaction of barbituric acid (BA), 1,3-dimethyl barbituric acid (DMBA) and 2-thiobarbituric acid (TBA) with cyanogen bromide and various aldehydes in presence of triethylamine afforded a new class of heterocyclic stable 5-alkyl and/or 5-aryl-1H, 1′H-spiro[furo[2,3-d]pyrimidine-6,5′-pyrimidine]2,2′,4,4′,6′(3H,3′H,5H)-pentaones which are dimeric forms of barbiturate (uracil and thiouracil derivatives) at 0 °C to ambient temperatures. Structure elucidation is proved by X-ray crystallography, 1H NMR, 13C NMR, FT-IR, CHN and mass analyses techniques. Mechanisms of the formations are discussed.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Urmia University, 57159, Urmia, Iran

    Mohammad Jalilzadeh, Nader Noroozi Pesyan, Fereshteh Rezaee, Saeed Rastgar & Yaser Hosseini

  2. Department of Chemistry, Faculty of Science, Atatürk University, 25240, Erzurum, Turkey

    Ertan Şahin

Authors
  1. Mohammad Jalilzadeh
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  2. Nader Noroozi Pesyan
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  3. Fereshteh Rezaee
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  4. Saeed Rastgar
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  5. Yaser Hosseini
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  6. Ertan Şahin
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Correspondence to Nader Noroozi Pesyan.

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Jalilzadeh, M., Noroozi Pesyan, N., Rezaee, F. et al. New one-pot synthesis of spiro[furo[2,3-d]pyrimidine-6,5′-pyrimidine]pentaones and their sulfur analogues. Mol Divers 15, 721–731 (2011). https://doi.org/10.1007/s11030-011-9302-9

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  • DOI: https://doi.org/10.1007/s11030-011-9302-9

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