Base-Catalyzed, Efficient Synthesis of 5-Substituted 3,6-Dihydro-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones

Jun-Feng Zhao; Chang Xie; Ming-Wu Ding; Hong-Wu He

doi:10.1055/s-2005-872077

PAPER

Base-Catalyzed, Efficient Synthesis of 5-Substituted 3,6-Dihydro-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones

Jun-Feng Zhao, Chang Xie, Ming-Wu Ding*, Hong-Wu He*
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, 430079, P. R. China
Fax: +86(27)67862041; e-Mail: mwding@mail.ccnu.edu.cn;

Abstract

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Abstract

The carbodiimides 2, obtained from aza-Wittig reactions of iminophosphorane 1 with aromatic isocyanates, reacted with secondary amines or ROH to give 5-dialkylamino or 5-alkoxy 7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones 4 in the presence of a catalytic amount of EtONa in a mixed solvent (CH₂Cl₂-ROH). Reactions of 2 with phenols in presence of catalytic potassium carbonate in MeCN gave 5-aryloxy-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones 4 in satisfactory yields.

Key words

pyrimidines - imides - cyclizations - aza-Wittig reactions - heterocycles - guanines

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References

1 Santana L. Teijeira M. Uriarte E. Balzarini J. De Clercq E. Eur. J. Med. Chem. 2002, 37: 755

2 Blanco JM. Caamano O. Fernandez F. Garcia-Mera X. Hergueta AR. Lopez C. Rodriguez-Borges JE. Balzarini J. De Clerco E. Chem. Pharm. Bull. 1999, 47: 1314

3 Nieto MI. Caamano O. Fernandez F. Gomez M. Balzarini J. De Clercq E. Nucleosides, Nucleotides Nucleic Acids 2002, 21: 243

4 Slusarchyk WA, and Zahler R. inventors; US 5723609. ; Chem. Abstr. 1998, 128, 230636c

5 Matthes E, Von Janta-Lipinski M, Reimer K, Mueller W, Meisel H, Lehmann C, and Schildt J. inventors; EP 409227. ; Chem. Abstr. 1991, 115, 159680m

6 Nielsen FE. Pedersen EB. Begtrup M. Liebigs Ann. Chem. 1984, 1848

7 Nogueras M. Melguizo M. Quijano ML. Sanchez A. J. Heterocycl. Chem. 1991, 28: 1417

8 Asenjo AR. Melgarejo SM. Noqueras MM. Rodriquez AM. Rodriquez MC. Sanchez RA. Nucleosides Nucleotides 1984, 3: 207

9 Ried W. Guryn R. Laoutidis J. Liebigs Ann. Chem. 1990, 819

10 Scheiner P. Arwin S. Eliacin M. Tu J. J. Heterocycl. Chem. 1985, 22: 1435

11 Sznaidman ML. Beauchamp LM. J. Heterocycl. Chem. 1996, 33: 1605

12 Chretien F. Gross B. Tetrahedron 1982, 38: 103

13 Ding MW. Xu SZ. Zhao JF. J. Org. Chem. 2004, 69: 8366

14 Ding MW. Chen YF. Huang NY. Eur. J. Org. Chem. 2004, 3872

15 Ding MW. Yang SJ. Zhu J. Synthesis 2004, 75

16 Ding MW. Fu BQ. Cheng L. Synthesis 2004, 1067

17 Ding MW. Sun Y. Liu XP. Liu ZJ. Org. Prep. Proced. Int. 2003, 35: 391

18 Chen M. Zheng Y. Gao G. Fan S. Lu S. Heterocycl. Commun. 2003, 9: 395

19 Wamhoff H. Haffmanns G. Chem. Ber. 1984, 117: 585

20 Chen MD. Yuan GP. Yang SY. Chin. J. Org. Chem. 2000, 20: 357

21 Chen M. Yuan G. Yang S. Synth. Commun. 2000, 30: 1287