A novel approach to phenanthro[9,10-d]pyrimidines via an intramolecular Stille-type biaryl coupling reaction

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7155-7158

  Olivera, Roberto ^a   Pascual, Sergio ^a   Herrero, Maite ^a   SanMartin, Raul ^a   Domínguez, Esther ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Coupling reactions; Policyclic heterocyclic compounds; Pyrimidines

Indexed keywords

ENAMINE; HETEROCYCLIC COMPOUND; KETONE DERIVATIVE; ORGANOMETALLIC COMPOUND; PHENANTHRENE DERIVATIVE; POLYCYCLIC HYDROCARBON; PYRIMIDINE DERIVATIVE; TIN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; MOLECULAR INTERACTION; STEREOSPECIFICITY;

EID: 0032563819     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01531-7     Document Type: Article

References (34)

1. 1 a. Chen, K-X; Gresh, N.; Pullman, B. Nucleic Acid Research, 1986, 14, 9103-9115;
2. b. Kumar, S. J. Org. Chem., 1997, 62, 8535-8539.
3. 2. a. Krmpotic, E.; Farnsworth, N.R.; Norman, R.; Messmer, M.W. J. Pharm. Sci., 1972, 61, 1508-1509;
4. b. Lou, H.; Li, X.; Chu, X-J.; Jiang, Z. Shandong YikeDaxue Xuebao, 1995, 33, 158-162 (CA 124:211689, 1996)
5. b. Lou, H.; Li, X.; Chu, X-J.; Jiang, Z. Shandong YikeDaxue Xuebao, 1995, 33, 158-162 (CA 124:211689, 1996)
6. 3. a. Mulchandani, N.B; Venkatachalam, N.B. Phytochemistry, 1972, 15, 1561-1563;
7. b. Al-Shamma, A.; Drake, S.D.; Guagliardi, L.E.; Swayze, J.K. Phytochemistry, 1982, 21, 485-487.
8. 4. a. Domínguez, E.; Ibeas, E.; Martinez de Marigorta, E.; Palacios, J.K.; SanMartin, R. J. Org. Chem., 1996, 61, 5435-5439;
9. b. For a tentative mechanism to explain pyrimidine formation from enaminones under Leuckart conditions see: Domínguez, E.; Martinez de Marigorta, E.; Olivera, R.; SanMartin, R. Synlett, 1995, 51, 525-526.
10. 5. Mallory, F.B.; Mallory, C.W. Org. React., 1984, 30, 1.
11. 6. a. Steliou, K.; Salama, P.; Xu, X. J. Am. Chem. Soc., 1992, 114, 1456-1462;
12. b. Goldfinger, M.B.; Crawfird, K.B.; Swager, T.M. J. Am. Chem. Soc., 1997, 119, 4578-4593.
13. 7. Larock, R.C.; Doty, M.J.; Tian, Q.; Zenner, J.M. J. Org. Chem., 1997, 62, 7536-7537.
14. 8. Moss, R.A.; Bracken, K.; Emge, T.J. J. Org. Chem., 1995, 60, 7739-7746.
15. 9. Wu, G.; Rheingold; A.L.; Geib, S.J.; Heck, R.F. Organometallics, 1987, 6, 1941-1946.
16. 10. a. SanMartin, R.; Domínguez, E.; Martinez de Marigorta, E. Tetrahedron, 1994, 50, 2255-2264 and references cited therein;
17. b. Olivera, R.; Domínguez, E.; SanMartin, R. unpublished results.
18. +, 32), 388 (M-2, 18), 311 (47), 319 (47), 230 (100), 176 (22).
19. 3): δ 140.5-141.6 (=CH-N), 158.4-162.0 (CO); EI-MS a: m/z 427 (M+2-CHO, 3), 427 (M-CHO, 6), 427 (M-2-CHO, 4), 374.1 (M-Br, 14), 372.1 (M-Br, 14), 346 (M-Br-CHO, 77), 344 (M-Br-CHO, 77), 264 (M-2Br-CHO, 100); b: m/z 534 ((M-CHO, 4), 408 (M-I-CHO, 17), 280 (M-2I-CHO, 100)
20. 13. Miyaura, N.; Suzuki, A. Chem. Rev., 1995, 95, 2457-2483 and references cited therein.
21. 14. a. Stille, J.K. Angew. Chem., Int, Ed. Engl., 1986, 25, 508-524;
22. b. Mitchell, T.N. Synthesis, 1992, 803-815.
23. 15. Peterson, M.A.; Mitchell, J.R. J. Org. Chem., 1997, 62, 8327-8329.
24. +, 100), 229 (16), 176 (28), 88 (21).
25. 17. Azarian, D.; Dua, S.S.; Eaborn, C.; Walton, D.R.M. J. Organomet. Chem., 1976, 117, C55-C57
26. 18. Wang, J.; Scott, A.I. Tetrahedron Lett., 1996, 37, 3247-3250
27. 2, hexane/EtOAc 8:2 as solvent) to afford phenanthro[9,10-d]pyrimidine 4a (25 mg, 89%) as a yellow powder.
28. 20. González, J.J.; García, N.; Gómez-Lor, B.; Echavarren, A.M. J. Org. Chem., 1997, 62, 1286-1291.
29. 21. Crystal structure of a 4,5-diarylsubstituted isoxazole shows a marked steric interaction between aryl groups. See: SanMartin, R.; Olivera, R.; Domínguez, E.; Xolans, X.; Urtiaga, M.K.; Font-Bardia, M. Cryst. Res. Technol., 1997, 32, 1015-1020.
30. 22. A proposal for the mechanism based on previous reports regarding Stille coupling reactions (Farina, V.; Krishnan, B. J. Am. Chem. Soc., 1991, 113, 9585) is shown below: (equation presented)
31. 23. Other examples of similar intramolecular couplings: a) Grigg, R.; Teasdale, A.; Sridharan, V. Tetrahedron Lett., 1991, 32, 3858-3862.
32. b) Kelly, T.R.; Xu, W.; Ma, Z.; Li, Q.; Bhushan, V. J. Am. Chem. Soc., 1993, 115, 5843-5844.
33. c) Barrett, A.G.M.; Boys, M.L.; Boehm, T.L. J. Chem. Soc., Chem. Commun., 1994, 16, 1881-1882.
34. d) Beddoes, R.L.; Cheeseright, T.; Wang, J.; Quayle, P. Tetrahedron Lett., 1995, 36, 283-286.