Literature DB >> 21279439

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

Mohammad Jalilzadeh1, Nader Noroozi Pesyan, Fereshteh Rezaee, Saeed Rastgar, Yaser Hosseini, Ertan Sahin.   

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, (1)H NMR, (13)C NMR, FT-IR, CHN and mass analyses techniques. Mechanisms of the formations are discussed.

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Year:  2011        PMID: 21279439     DOI: 10.1007/s11030-011-9302-9

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  12 in total

1.  Determination of nikethamide with cyanogen bromide and barbituric acid.

Authors:  O PELLETIER; J A CAMPBELL
Journal:  J Pharm Sci       Date:  1962-06       Impact factor: 3.534

2.  Direct determination of niacinamide in multivitamin preparations.

Authors:  O PELLETIER; J A CAMPBELL
Journal:  J Pharm Sci       Date:  1961-11       Impact factor: 3.534

3.  SHELXL: high-resolution refinement.

Authors:  G M Sheldrick; T R Schneider
Journal:  Methods Enzymol       Date:  1997       Impact factor: 1.600

4.  Synthesis and properties of spiro nucleosides containing the barbituric acid moiety.

Authors:  Annabelle Renard; Jean Lhomme; Mitsuharu Kotera
Journal:  J Org Chem       Date:  2002-02-22       Impact factor: 4.354

5.  Synthesis of some ureidodihydrofurans and related pyrimidones as potential antimalarials.

Authors:  E Campaigne; R L Ellis; M Bradford; J Ho
Journal:  J Med Chem       Date:  1969-03       Impact factor: 7.446

6.  Barbituric acid as a substituent at aryl methylium ions.

Authors:  Stefan Spange; Mirko Bauer; Bernhard Walfort; Heinrich Lang
Journal:  J Org Chem       Date:  2006-09-29       Impact factor: 4.354

7.  Spiro-annulation of barbituric acid derivatives and its analogs by ring-closing metathesis reaction.

Authors:  Sambasivarao Kotha; Ashoke Chandra Deb; Ramanatham Vinod Kumar
Journal:  Bioorg Med Chem Lett       Date:  2005-02-15       Impact factor: 2.823

8.  Unique charge-separated pyridinium-barbituric acid zwitterions.

Authors:  Branko S Jursic; Donna M Neumann; Zakhia Moore; Edwin D Stevens
Journal:  J Org Chem       Date:  2002-04-05       Impact factor: 4.354

9.  Facile synthesis of a fullerene-barbituric acid derivative and supramolecular catalysis of its photoinduced dimerization.

Authors:  Nathan D McClenaghan; Christelle Absalon; Dario M Bassani
Journal:  J Am Chem Soc       Date:  2003-10-29       Impact factor: 15.419

10.  Tautomeric behaviour and isotopic multiplets in the 13C NMR spectra of partially deuterated 5-arylazo-pyrimidine (1H,3H,5H)-2,4,6-triones and 5-arylazo-2-thioxo-pyrimidine (1H,3H,5H)-4,6-diones-evidence for elucidation of tautomeric forms.

Authors:  Nader Noroozi Pesyan
Journal:  Magn Reson Chem       Date:  2009-11       Impact factor: 2.447

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  1 in total

1.  The Hydrogen Bonded Structures of Two 5-Bromobarbituric Acids and Analysis of Unequal C5-X and C5-X' Bond Lengths (X = X' = F, Cl, Br or Me) in 5,5-Disubstituted Barbituric Acids.

Authors:  Thomas Gelbrich; Doris E Braun; Stefan Oberparleiter; Herwig Schottenberger; Ulrich J Griesser
Journal:  Crystals (Basel)       Date:  2016-04-22       Impact factor: 2.589

  1 in total

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