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Collect. Czech. Chem. Commun. 1995, 60, 1386-1389
https://doi.org/10.1135/cccc19951386

A Facile Synthesis of 6-Cyanopurine Bases

Michal Hocek and Antonín Holý

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic

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  • Mahajan Tushar, Ytre-Arne Mari, Strøm-Andersen Pernille, Dalhus Bjørn, Gundersen Lise-Lotte: Synthetic Routes to N-9 Alkylated 8-Oxoguanines; Weak Inhibitors of the Human DNA Glycosylase OGG1. Molecules 2015, 20, 15944. <https://doi.org/10.3390/molecules200915944>
  • Hasník Zbyněk, Pohl Radek, Hocek Michal: Synthesis of (purin-6-yl)methylphosphonate bases and nucleosides. Tetrahedron Letters 2010, 51, 2464. <https://doi.org/10.1016/j.tetlet.2010.02.167>
  • Hasník Zbyněk, Pohl Radek, Klepetářová Blanka, Hocek Michal: Synthesis of (purin-6-yl)acetates and their transformations to 6-(2-hydroxyethyl)- and 6-(carbamoylmethyl)purines. Collect. Czech. Chem. Commun. 2009, 74, 1035. <https://doi.org/10.1135/cccc2009042>
  • Bambuch Vítězslav, Pohl Radek, Hocek Michal: Synthesis of 6‐(4,5‐Dihydrofuran‐2‐yl)‐ and 6‐(Tetrahydrofuran‐2‐yl)purine Bases and Nucleosides. Eur J Org Chem 2008, 2008, 2783. <https://doi.org/10.1002/ejoc.200800174>
  • Dias Alice M., Cabral Isabel, Vila‐Chã A. Sofia, Costa Daniela S., Proença M. Fernanda: The Synthesis of 6‐Amidino‐2‐oxopurine Revisited: New Evidence for the Reaction Mechanism. Eur J Org Chem 2007, 2007, 1925. <https://doi.org/10.1002/ejoc.200601025>
  • Hasník Zbyněk, Šilhár Peter, Hocek Michal: Synthesis of (purin-6-yl)acetates and 6-(2-hydroxyethyl)purines via cross-couplings of 6-chloropurines with the Reformatsky reagent. Tetrahedron Letters 2007, 48, 5589. <https://doi.org/10.1016/j.tetlet.2007.06.053>
  • Kuchař Martin, Pohl Radek, Votruba Ivan, Hocek Michal: Synthesis of Purines Bearing Functionalized C‐Substituents by the Conjugate Addition of Nucleophiles to 6‐Vinylpurines and 6‐Ethynylpurines. Eur J Org Chem 2006, 2006, 5083. <https://doi.org/10.1002/ejoc.200600545>
  • Maydanovych Olena, Beal Peter A.: C6-Substituted Analogues of 8-Azanebularine:  Probes of an RNA-Editing Enzyme Active Site. Org. Lett. 2006, 8, 3753. <https://doi.org/10.1021/ol061354j>
  • Šilhár Peter, Pohl Radek, Votruba Ivan, Hocek Michal: The first synthesis and cytostatic activity of novel 6-(fluoromethyl)purine bases and nucleosides. Org. Biomol. Chem. 2005, 3, 3001. <https://doi.org/10.1039/b508122j>
  • Šilhár Peter, Pohl Radek, Votruba Ivan, Hocek Michal: Synthesis of 2-Substituted 6-(Hydroxymethyl)purine Bases and Nucleosides. Collect. Czech. Chem. Commun. 2005, 70, 1669. <https://doi.org/10.1135/cccc20051669>
  • Šilhár Peter, Pohl Radek, Votruba Ivan, Hocek Michal: Facile and Efficient Synthesis of 6-(Hydroxymethyl)purines. Org. Lett. 2004, 6, 3225. <https://doi.org/10.1021/ol049059r>
  • Hocek Michal: Syntheses of Purines Bearing Carbon Substituents in Positions 2, 6 or 8 by Metal‐ or Organometal‐Mediated C−C Bond‐Forming Reactions. Eur J Org Chem 2003, 2003, 245. <https://doi.org/10.1002/ejoc.200390025>
  • Hocek Michal, Dvořáková Hana: An Efficient Synthesis of 2-Substituted 6-Methylpurine Bases and Nucleosides by Fe- or Pd-Catalyzed Cross-Coupling Reactions of 2,6-Dichloropurines. J. Org. Chem. 2003, 68, 5773. <https://doi.org/10.1021/jo034351i>
  • Česnek Michal, Holý Antonı́n, Masojı́dková Milena: 6-Guanidinopurine nucleosides and their analogues. Tetrahedron 2002, 58, 2985. <https://doi.org/10.1016/S0040-4020(02)00186-2>
  • Hocek Michal, Stará Irena G., Starý Ivo, Dvořáková Hana: Covalent Analogues of DNA Base-Pairs and Triplets IV. Synthesis of Trisubstituted Benzenes Bearing Purine and/or Pyrimidine Rings by Cyclotrimerization of 6-Ethynylpurines and/or 5-Ethynyl-1,3-dimethyluracil. Collect. Czech. Chem. Commun. 2002, 67, 1223. <https://doi.org/10.1135/cccc20021223>
  • Milecki Jan, Földesi Andras, Fischer Artur, Adamiak Ryszard W., Chattopadhyaya Jyoti: Synthesis of multiply labelled ribonucleosides for sequence‐specific labelling of oligo‐RNA. Labelled Comp Radiopharmac 2001, 44, 763. <https://doi.org/10.1002/jlcr.503>
  • Hocek Michal, Stará Irena G, Starý Ivo, Dvořáková Hana: Cyclotrimerization of 6-ethynylpurines. Synthesis of 1,2,4- and 1,3,5-tris(purin-6-yl)benzenes as novel Hoogsteen-triplet analogues. Tetrahedron Letters 2001, 42, 519. <https://doi.org/10.1016/S0040-4039(00)01989-4>
  • Hocek Michal, Masojídková Milena, Holý Antonín: Synthesis of acyclic nucleotide analogues derived from N-substituted 6-(1-aminoethyl)purines via 6-acetylpurine derivatives. Tetrahedron 1997, 53, 2291. <https://doi.org/10.1016/S0040-4020(96)01130-1>
  • HOCEK M., HOLY A.: ChemInform Abstract: A Facile Synthesis of 6‐Cyanopurine Bases. ChemInform 1996, 27. <https://doi.org/10.1002/chin.199605181>