2,6-Diamino-5,8-diaza-7,9-dicarba-purine

Organic Letters

Volumn 5, Issue 12, 2003, Pages 2067-2070

  Wang, Zhijun ^a   Huynh, Hoan K ^a   Han, Bo ^b   Krishnamurthy, Ramanarayanan ^a   Eschenmoser, Albert ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2,6 DIAMINO 5,8 DIAZA 7,9 DICARBAPURINE; 2,6 DIAMINOPURINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

2-AMINOPURINE; AZA COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; PURINE NUCLEOSIDES; PURINES; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0141451973     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol030044n     Document Type: Article

References (28)

1. Chemistry of α-Aminonitriles. Part 39. For Part 38, see: Jungmann, O.; Beier, M.; Luther, A.; Huynh, H. K.; Ebert, M. O.; Jaun, B.; Krishnamurthy, R.; Eschenmoser, A. Helv. Chim. Acta 2003, in press.
2. Chemistry of α-Aminonitriles. Part 39. For Part 38, see: Jungmann, O.; Beier, M.; Luther, A.; Huynh, H. K.; Ebert, M. O.; Jaun, B.; Krishnamurthy, R.; Eschenmoser, A. Helv. Chim. Acta 2003, in press.
3. Schöning, K.-U.; Scholz, P.; Guntha, S.; Wu, X.; Krishnamurthy, R.; Eschenmoser, A. Science 2000, 290, 1347. Schöning, K.-U.; Scholz, P.; Wu, X.; Guntha, S.; Delgado, G.; Krishnamurthy, R.; Eschenmoser, A. Helv. Chim. Acta 2002, 85, 4111.
4. Schöning, K.-U.; Scholz, P.; Guntha, S.; Wu, X.; Krishnamurthy, R.; Eschenmoser, A. Science 2000, 290, 1347. Schöning, K.-U.; Scholz, P.; Wu, X.; Guntha, S.; Delgado, G.; Krishnamurthy, R.; Eschenmoser, A. Helv. Chim. Acta 2002, 85, 4111.
5. Wu, X.; Guntha, S.; Ferencic, M.; Krishnamurthy, R.; Eschenmoser, A. Org. Lett. 2002, 4, 1279.
6. Wu, X.; Delgado, G.; Krishnamurthy, R.; Eschenmoser, A. Org. Lett. 2002, 4, 1283.
7. Reist, E. J.; Fisher, L. V.; Goodman, L. J. Org. Chem. 1967, 32, 2541. Altman, K.-H. Tetrahedron Lett. 1993, 34, 7721. Rassu, G.; Pinna, L.; Spanu, P. ; Ulgheri, F.; Casiraghi, G. Tetrahedron Lett. 1994, 35, 4019.
8. Reist, E. J.; Fisher, L. V.; Goodman, L. J. Org. Chem. 1967, 32, 2541. Altman, K.-H. Tetrahedron Lett. 1993, 34, 7721. Rassu, G.; Pinna, L.; Spanu, P. ; Ulgheri, F.; Casiraghi, G. Tetrahedron Lett. 1994, 35, 4019.
9. Reist, E. J.; Fisher, L. V.; Goodman, L. J. Org. Chem. 1967, 32, 2541. Altman, K.-H. Tetrahedron Lett. 1993, 34, 7721. Rassu, G.; Pinna, L.; Spanu, P. ; Ulgheri, F.; Casiraghi, G. Tetrahedron Lett. 1994, 35, 4019.
10. Häberle, A.; Leumann, C. J. Org. Lett. 2001, 3, 489 and references therein. Evans, G. B.; Furneaux, R. H.; Hutchinson, T. L.; Kezar, H. S.; Morris, P. E., Jr.; Schramm, V. L.; Tyler, P. C. J. Org. Chem. 2001, 66, 5723.
11. Häberle, A.; Leumann, C. J. Org. Lett. 2001, 3, 489 and references therein. Evans, G. B.; Furneaux, R. H.; Hutchinson, T. L.; Kezar, H. S.; Morris, P. E., Jr.; Schramm, V. L.; Tyler, P. C. J. Org. Chem. 2001, 66, 5723.
12. Oro, J. Nature 1961, 190, 389. Ferris, J. P.; Hagan, W. J., Jr. Tetrahedron 1984, 40, 1093 (review).
13. Oro, J. Nature 1961, 190, 389. Ferris, J. P.; Hagan, W. J., Jr. Tetrahedron 1984, 40, 1093 (review).
14. A preparation of 1 had been previously attempted in the course of an extended study of the chemistry of substituted 5,8-diaza-7,9-dicarbapurine derivatives by Al-Shaar, A. H. M.; Chambers, R. K.; Gilmour, D. W.; Lythgoe, D. J.; McClenaghan, I.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1992, 2789.
15. Martin, K.; Matthews, H. R.; Rapoport, H.; Thyagarajan, G. J Org. Chem. 1968, 33, 3758.
16. Holter, S. N.; Fernlius, W. C. Inorg. Synth. 1963, 7, 58. Shirai, K.; Sugino, K. J. Org. Chem. 1960, 25, 1045.
17. Holter, S. N.; Fernlius, W. C. Inorg. Synth. 1963, 7, 58. Shirai, K.; Sugino, K. J. Org. Chem. 1960, 25, 1045.
18. Overberger, C. G.; Michelotti, F. W.; Carabateas, P. M. J. Am. Chem. Soc. 1957, 941, 79.
19. 13C, and HMB correlations.
20. -).
21. Carried out by Raj K. Chadha, TSRI. Crystallographic data for the structure has been deposited with the Cambridge Crystallographic Data Center as deposition no. CCDC 180981. Copies of the data can be obtained, free of charge, on application to the CCDC, 12 union Road, Cambridge CB12 1EZ UK (fax, + 44 (1233) 336 0333; E-mail, deposit@ccdc.cam.ac.uk). Data for 7 in Supporting Information.
22. Rabinowitz, J. C. J. Biol Chem. 1956, 218, 175.
23. Purchased from Aldrich, 96% purity.
24. Schreiber, J.; Maag, H.; Hashimoto, N.; Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1971, 10, 330.
25. Data for 9 in Supporting Information.
26. Poisel, H. Monatsh. Chem. 1978, 109, 925.
27. Data for 10 in Supporting Information.
28. Han, B.; Wang, Z.; Krishnamurthy, R., Jaun, B., Eschenmoser, A. Org. Lett. 2003, 5, 2071.