Synthesis of a cyclic tetrameric purine by successive cross-coupling reactions and subsequent Pd-catalyzed cyclization

European Journal of Organic Chemistry

Volumn , Issue 4, 2007, Pages 632-638

  Guthmann, Holger ^a   Könemann, Martin ^b   Bach, Thorsten ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b BASF AG   (Germany)

Author keywords

Cross coupling; Dyes; Halogenation; Metalation; Nitrogen heterocycles; Pigments

Indexed keywords

EID: 33846573350     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600724     Document Type: Article

References (50)

1. rd ed., Wiley-VCH, Weinheim, 2003;
2. b) H. Zollinger, Farbe - Eine multidisziplinäre Betrachtung, Wiley-VCH, Weinheim, 2005.
3. Review: H. Mustroph, M. Stollenwerk, V. Bressau, Angew. Chem. 2006, 118, 2068-2087;
4. Angew. Chem. Int. Ed. 2006, 45, 2016-2035.
5. Review: M. Grätzel, Inorg. Chem. 2005, 44, 6841-6851.
6. Review: R. Bonnett, J. Heterocycl. Chem. 2002, 39, 455-470.
7. E. Tauer, Synthesis 2002, 723-725.
8. For general reviews on the synthesis of purines, see: a) F. Seela, N. Ramzaeva, H. Rosemeyer, in: Science of Synthesis - Houben-Weyl Methods of Molecular Transformations, vol. 16 (Ed.: Y. Yamamoto), Thieme, Stuttgart, 2004, 945-1108;
9. b) F. Seela, N. Ramzaeva, H. Rosemeyer, in: Methoden der Organischen Chemie (Houben-Weyl), 4th ed., vol. E 9b/2 (Ed.: E. Schaumann), Thieme, Stuttgart, 1998, 304-546;
10. c) G. Shaw, in: Comprehensive Heterocyclic Chemistry, vol. 5 (Eds.: A. R. Katritzky, C. W. Rees), Pergamon Press, Oxford, 1984, 499-605;
11. nd ed., vol. 7 (Eds.: A. R. Katritzky, C. W. Rees), Pergamon Press, Oxford, 1996, 397-429;
12. e) J. Lister (Ed.), The Chemistry of Heterocyclic Compounds, vol. 56, Wiley-Interscience, New York, 1996.
13. Review: M. Hocek, Eur. J. Org. Chem. 2003, 245-254.
14. Review: S. Schröter, C. Stock, T. Bach, Tetrahedron 2005, 61, 2245-2267.
15. a) J. M. J. Nolsoe, L.-L. Gundersen, F. Rise, Acta Chem. Scand. 1999, 53, 366-372;
16. b) A. Bråthe, L.-L. Gundersen, J. Nissen-Meyer, F. Rise, B. Spilsberg, Bioorg. Med. Chem. Lett. 2003, 13, 877-880;
17. c) M. Hocek, D. Hocková, H. Dvořáková, Synthesis 2004, 889-894.
18. 8-Metalated purines are known to be stabilized as compared to 2- and 6-metalated purines, see T. Tobrman, D. Dvořák, Org. Lett. 2006, 8, 1291-1294 and refs. cited therein.
19. a) D. H. R. Barton, C. J. R. Hedgerock, E. Lederer, W. B. Motherwell, Tetrahedron Lett. 1979, 20, 279-280;
20. b) N. J. Leonard, J. D. Bryant, J. Org. Chem. 1979, 44, 4612-4616;
21. c) H. Tanaka, Y. Uchida, M. Shinozaki, H. Hayakawa, A. Matsuda, T. Miyasaka, Chem. Pharm. Bull. 1983, 31, 787-790;
22. d) H. Hayakawa, K. Haraguchi, H. Tanaka, T. Miyasaka, Chem. Pharm. Bull. 1987, 35, 72-79.
23. The preparation of diiodopurines has been attempted by iodode-chlorination. The reaction remained incomplete for 2,6-dichloropurine: G. B. Elion, G. H. Hitchings, J. Am. Chem. Soc. 1956, 78, 3508-3510.
24. 2-Chloro-6,8-diiodopurine was obtained from 2,6,8-trichloropurine: H. Ballweg, Justus Liebigs Ann. Chem. 1961, 649, 114-124.
25. a) Y. H. Kim, Phosphorus Sulfur Silicon Relat. Elem. 1993, 74, 249-260;
26. b) M. Brændvang, L.-L. Gundersen, Bioorg. Med. Chem. 2005, 13, 6360-6373.
27. J. M. J. Nolsoe, L.-L. Gundersen, F. Rise, Synth. Commun. 1998, 28, 4303-4315.
28. a) E. Negishi, A. O. King, N. Okukado, J. Org. Chem. 1977, 42, 1821-1823;
29. nd ed. (Ed.: M. Schlosser), Wiley, New York, 2002, 656-657.
30. S. Dey, P. Garner, J. Org. Chem. 2000, 65, 7697-7699.
31. a) Z. Janeba, A. Holy, M. Masojídková, Collect. Czech. Chem. Commun. 2000, 65, 1126-1144;
32. b) K. Meszárosová, A. Holý, M. Masojí dková, Collect. Czech. Chem. Commun. 2000, 65, 1109-1125.
33. P. Francom, M. J. Robins, J. Org. Chem. 2003, 68, 666-669.
34. a) J. A. Montgomery, C. Temple, J. Am. Chem. Soc. 1961, 83, 630-635;
35. b) L.-L. Gundersen, A. K. Bakkesturen, A. J. Aasen, H. Overas, F. Rise, Tetrahedron 1994, 50, 9743-9756.
36. a) P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117-2188;
37. b) E. Ender, Organozinc reagents in organic synthesis, CRC Press, Boca Raton, 1996.
38. A. S. B. Prasad, T. M. Stevenson, J. R. Citineni, V. Nyzam, P. Knochel, Tetrahedron 1997, 53, 7237-7254.
39. a) G. Heckmann, T. Bach, Angew. Chem. 2005, 117, 1223-1226;
40. Angew. Chem. Int. Ed. 2005, 44, 1199-1201;
41. b) O. Delgado, G. Heckmann, H. M. Müller, T. Bach, J. Org. Chem. 2006, 71, 4599-4608.
42. T. C. McKenzie, J. W. Epstein, J. Org. Chem. 1982, 47, 4881-4884.
43. Review: P. Knochel, W. Dohle, N. Gommermann, F. F. Kneisel, F. Kopp, T. Korn, I. Sapountzis, V. A. Vu, Angew. Chem. 2003, 115, 4438-4456;
44. Angew. Chem. Int. Ed. 2003, 42, 4302-4320.
45. A. Krasovskiy, P. Knochel, Angew. Chem. 2004, 116, 3396-3399;
46. Angew. Chem. Int. Ed. 2004, 43, 3333-3336.
47. a) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321;
48. nd ed. (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004, 1-40.
49. V. Farina, B. Krishnan, J. Am. Chem. Soc. 1991, 113, 9585-9595.
50. C. Santelli-Rouvier, C. Coin, L. Toupet, M. Santelli, J. Organomet. Chem. 1995, 91-96.