A convenient approach to heterocyclic building blocks: Synthesis of novel ring systems containing a [5,6]pyrano[2,3-c]pyrazol-4(1H)-one moiety

Molecules

Volumn 12, Issue 1, 2007, Pages 60-73

  Eller, Gernot A ^a   Holzer, Wolfgang ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Acylations; Fused ring systems; Heterocyclic building blocks; NMR spectroscopy; Pyrazolones

Indexed keywords

CARBON; HETEROCYCLIC COMPOUND; NITROGEN; PYRAN DERIVATIVE; PYRAZOLE DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

CARBON ISOTOPES; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NITROGEN ISOTOPES; PYRANS; PYRAZOLES;

EID: 33846990442     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12010060     Document Type: Article

References (37)

1. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Analysis of the reactions used for the preparation of drug candidate molecules. Org. Biomol. Chem. 2006, 4, 2337-2347.
2. th ed.; Wiley-Interscience: New York, 2003;
3. [Chem. Abstr. 2005, 143, 109740].
4. Makriyannis, A.; Biegel, D. Drug Discovery Strategies and Methods; Marcel Dekker, Inc.: New York, 2004;
5. [Chem. Abstr. 2004, 140, 229394].
6. Eller, G. A.; Wimmer, V.; Haring, A. W.; Holzer, W. An Efficient Approach to Heterocyclic Analogues of Xanthone: A Short Synthesis of all possible Pyrido[5,6]pyrano[2,3-c]pyrazol-4(1H)-ones. Synthesis 2006, 4219-4229.
7. Eller, G. A.; Haring, A. W.; Datterl, B.; Zwettler, M.; Holzer, W. Tri- and Tetracyclic Heteroaromatic Systems: Synthesis of Novel Benzo-, Benzothieno- and Thieno-Fused Pyrano[2,3-c]pyrazol-4(1H)-ones. Heterocycles 2007, 71, 87-104.
8. Eller, G. A.; Datterl, B.; Holzer, W.; manuscript submitted.
9. th ed.; Thieme: Stuttgart, 2001; p. 99.
10. Bell, J. Amlexanox for the Treatment of Recurrent Aphthous Ulcers. Clin. Drug Invest. 2005, 25, 555-566.
11. Colotta, V.; Cecchi, L.; Catarzi, D.; Melani, F.; Filacchioni, G.; Martini, C.; Tacchi, P.; Lucacchini, A. 1-(3-Aminophenyl)-3-methyl[1] benzopyrano[2,3-c]pyrazol-4-one: a new selective A2 adenosine receptor antagonist. Pharm. Pharmacol. Lett. 1992, 2, 74-76;
12. [Chem. Abstr. 1993, 118, 32807].
13. Eller, G. A.; Holzer, W. The 4-Methoxybenzyl (PMB) Function as a Versatile Protecting Group in the Synthesis of N-Unsubstituted Pyrazolones. Heterocycles 2004, 63, 2537-2555.
14. Holzer, W.; Eller, G. A.; Wimmer, V.; Haring, A.; manuscript in preparation.
15. Minkin, V. I.; Garnovskii, A. D.; Elguero, J.; Katritzky, A. R.; Denisko, O. V. The tautomerism of heterocycles: Five-membered rings with two or more heteroatoms. Adv. Heterocycl. Chem. 2000, 76, 157-323;
16. [Chem. Abstr. 2000, 133, 309576].
17. Jensen, B. S. Synthesis of 1-phenyl-3-methyl-4-acyl-5-pyrazolones. Acta Chem. Scand. 1959, 13, 1668-1670;
18. [Chem. Abstr. 1962, 56, 66890].
19. Williams, A. Recent advances in NMR prediction and automated structure elucidation software. Curr. Opin. Drug Discovery Dev. 2000, 3, 298-305;
20. [Chem. Abstr. 2000, 133, 222096].
21. NMRPredict, version 3.2.8; Modgraph Consultants, Ltd.: Herts, United Kingdom, 2004; www.modgraph.co.uk.
22. ACD/C+H NMR Predictors and DB, version 10.04; Advanced Chemistry Development, Inc.: Toronto, ON, Canada, 2006; www.acdlabs.com.
23. nd ed.; Wiley-VCH: Weinheim, 1998;
24. [Chem. Abstr. 1999, 131, 184497].
25. nd ed.; Wiley-VCH, Inc.: New York, 2000;
26. [Chem. Abstr. 2004, 142, 392075].
27. 1-determinations of heteronuclear distances., Prog. Nucl. Magn. Reson. Spectrosc. 1987, 19, 223-266;
28. [Chem. Abstr. 1987, 107, 145869].
29. Szántay, C, Jr.; Csepregi, Z.; Aranyosi, P.; Ruznák, I.; Töke, L.; Víg, A. Nuclear Magnetic Resonance Investigations of the Azo-Hydrazone Tautomerism of Azoreactive Dye Chromophores, Magn. Reson. Chem. 1997, 35, 306-310;
30. [Chem. Abstr. 1997, 126, 294555].
31. Davis, D. G.; Bax, A. Simplification of proton NMR spectra by selective excitation of experimental subspectra. J. Am. Chem. Soc. 1985, 107, 7197-7198.
32. Sarkar, S. K.; Bax, A. A simple and sensitive one-dimensional NMR technique for correlation of proton and carbon chemical shifts. J. Magn. Reson. 1985, 62, 109-112.
33. Bax, A. Structure determination and spectral assignment by pulsed polarization transfer via long-range proton-carbon-13 couplings. J. Magn. Reson. 1984, 57, 314-318.
34. Jippo, T.; Kamo, O.; Nagayama, N. Determination of long-range proton-carbon 13 coupling constants with selective two-dimensional INEPT. J. Magn. Reson. 1986, 66, 344-348.
35. Willker, W.; Leibfritz, D.; Kerssebaum, R.; Bermel, W. Gradient selection in inverse heteronuclear correlation spectroscopy. Magn. Reson. Chem. 1993, 31, 287-292.
36. ACD/Name, version 10.01; Advanced Chemistry Development, Inc.: Toronto, ON, Canada, 2006; www.acdlabs.com.
37. Eller, G. A. Improving the Quality of Published Chemical Names with Nomenclature Software. Molecules 2006, 11, 915-928.