Suzuki-Miyaura and Negishi approaches to a series of forensically relevant pyridines and pyrimidines

Synthesis

Volumn , Issue 21, 2011, Pages 3496-3506

  Błachut, Dariusz ^b   Szawkało, Joanna ^a   Czarnocki, Zbigniew ^a  

^a UNIVERSITY OF WARSAW   (Poland)

^b Agencja Bezpieczenstwa Wewnetrznego Warszawa   (Poland)

Author keywords

amphetamine analogues; cross coupling reaction; drugs; heterocycles; Leuckart synthesis

Indexed keywords

AMPHETAMINE ANALOGUES; CROSS-COUPLING REACTION; DRUGS; HETEROCYCLES; LEUCKART SYNTHESIS;

SYNTHESIS (CHEMICAL);

2,6 BIS(2 FLUOROBENZYL)PYRIDINE; 2,6 BIS(4 FLUOROBENZYL)PYRIDINE; 2,6 DIBENZYLPYRIDINE; 4 (2 FLUOROBENZYL)PYRIMIDINE; 4 (2 METHOXYBENZYL)PYRIMIDINE; 4 (2,5 DIMETHOXYBENZYL)PYRIMIDINE; 4 (3 METHOXYBENZYL)PYRIMIDINE; 4 (3,4,5 TRIMETHOXYBENZYL)PYRIMIDINE; 4 (4 FLUOROBENZYL)PYRIMIDINE; 4 (4 METHOXYBENZYL)PYRIMIDINE; 4 (4 METHYLTHIOBENZYLO)PYRIMIDINE; 4 BENZYLPYRIMIDINE; 4 METHYL 5 (3,4 METHYLENEDIOXYPHENYL)PYRIMIDINE; 4 METHYL 5 (3,4,5 TRIMETHOXYPHENYL)PYRIMIDINE; 4 METHYL 5 [3 (TRIFLUOROMETHYL)PHENYL]PYRIMIDINE; 4 METHYL 5 [4 (METHYLTHIO)PHENYL]PYRIMIDINE; 5 (2 ETHOXYPHENYL) 4 METHYLPYRIMIDINE; 5 (2 FLUOROPHENYL) 4 METHYLPYRIMIDINE; 5 (2 METHOXYPHENYL) 4 METHYLPYRIMIDINE; 5 (2,5 DIMETHOXYPHENYL) 4 METHYLPYRIMIDINE; 5 (3 FLUOROPHENYL) 4 METHYLPYRIMIDINE; 5 (3 METHOXYPHENYL) 4 METHYLPYRIMIDINE; 5 (4 FLUOROPHENYL) 4 METHYLPYRIMIDINE; 5 (4 METHOXYPHENYL) 4 METHYLPYRIMIDINE; 5 PHENYL 4 METHYLPYRIMIDINE; ARYLBORONIC ACID; BORONIC ACID DERIVATIVE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; FORENSIC SCIENCE; SYNTHESIS;

EID: 80054854558     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260224     Document Type: Article

References (39)

1. (a) Joule, J. A.; Mills, K.; Smith, G. F. In Heterocyclic Chemistry; Chapman & Hall: London, 1995.
2. (b) Itami, K.; Yamazaki, D.; Yoshida, J.-i. J. Am. Chem. Soc. 2004, 126, 15396.
3. (c) Baldwin, B. C.; Corran, A. J.; Robson, M. J. Pestic. Sci. 1995, 44, 81.
4. (d) Wong, K.-T.; Hung, T. S.; Wu, Ch. Ch.; Lee, G.-H.; Peng, S.-M.; Chou, Ch.-S.; Su, Y. O. Org. Lett. 2002, 4, 513.
5. (a) van der Ark, A. M.; Sinnema, A.; Theeuwen, A. B. E.; van der Torn, J. M.; Verweij, A. M. A. Pharm. Weekbl. 1978, 113, 41.
6. (b) van der Ark, A. M.; Sinnema, A.; van der Torn, J. M.; Verweij, A. M. A. Pharm. Weekbl. 1978, 113, 341.
7. (c) van der Ark, A. M.; Verweij, A. M. A.; Sinnema, A. J. Forensic Sci. 1978, 23, 693.
8. (a) Cloonan, S. M.; Keating, J. J.; Corrigan, D.; O'Brien, J. E.; Kavanagh, P. V.; Wiliams, D. C.; Meegan, M. J. Bioorg. Med. Chem. 2010, 18, 4009.
9. (b) Bohn, M.; Bohn, G.; Blaschke, G. Int. J. Leg. Med. 1993, 106, 19.
10. (c) Błachut, D.; Wojtasiewicz, K.; Czarnocki, Z. Forensic Sci. Int. 2005, 152, 157.
11. (a) Sinnema, A.; Verweij, A. M. A. Bull. Narc. 1981, 33, 37.
12. (b) Verweij, A. M. A. Forensic Sci. Rev. 1989, 1, 1.
13. Waumans, D.; Bruneel, N.; Tytgat, J. Forensic Sci. Int. 2003, 133, 159.
14. Błachut, D.; Wojtasiewicz, K.; Krawczyk, K.; Maurin, J.; Szawkało, J.; Czarnocki, Z. Forensic Sci. Int. 2011, in press.
15. (a) Błachut, D.; Wojtasiewicz, K.; Czarnocki, Z. Forensic Sci. Int. 2002, 127, 45.
16. (b) Błachut, D.; Maurin, J. K.; Starosta, W.; Wojtasiewicz, K.; Czarnocki, Z. Z. Naturforsch., B 2002, 57, 593.
17. (c) Błachut, D.; Danikiewicz, W.; Wojtasiewicz, K.; Olejnik, M.; Kalinowska, I.; Szawkało, J.; Czarnocki, Z. Forensic Sci. Int. 2011, 206, 197.
18. (a) Dodson, R. M.; Sayler, J. K. J. Org. Chem. 1952, 16, 461.
19. (b) Muller, T. J. J.; Braun, R.; Ansorge, M. Org. Lett. 2000, 2, 1967.
20. (a) Koyama, T.; Hirota, T.; Bashon, C.; Satoh, Y.; Shinhara, Y.; Watanabe, Y.; Matsumoto, S.; Shinohara, Y.; Ohmori, S.; Yamato, M. Chem. Pharm. Bull. 1975, 23, 2158.
21. (b) Kirkbridge, K. P.; Ward, A. D.; Jenkins, N. F.; Klass, G.; Coumbaros, J. C. Forensic Sci. Int. 2001, 115, 53.
22. Błachut, D.; Czarnocki, Z.; Wojtasiewicz, K. Synthesis 2006, 2855.
23. Schröter, S.; Stock, Ch.; Bach, T. Tetrahedron 2005, 61, 2245.
24. Schomaker, J. M.; Delia, T. J. J. Org. Chem. 2001, 66, 7125.
25. Parry, P. R.; Wang, Ch.; Batsanov, A. S.; Bryce, M. R.; Tarbit, B. J. Org. Chem. 2002, 67, 7541.
26. Ceide, S. C.; Montalban, A. G. Tetrahedron Lett. 2006, 47, 4415.
27. (a) Van der Plas, H. C. Rec. Trav. Chim. Bays-Pas 1965, 84, 1101.
28. (b) Yamanaka, H.; Sakamoto, T.; Nishimura, S.; Sagi, M. Chem. Pharm. Bull. 1987, 35, 3119.
29. The outcome of the reactions was controlled by GC-MS. The advantage of the GC-MS method is that it can be applied to complicated mixtures of compounds, providing useful information of their composition and the products ratio. Obviously, the differences in the mass spectra of closely related isomers cannot be spectacular but due to a similar fragmentation routes, the total ion current should be similar for substrate, final products and by-products formed. Consequently, the intensities (peak area) of the peaks in chromatograms are a good measure for the proportion of substances in the mixture. In our case, the conversion was calculated by comparison of the peak area of remaining substrate with a sum of peak areas of the final product and by-products. The yield of a particular component was calculated by comparing of a peak area of the product with a sum of peak areas recorded for remaining products and substrate (if present).
30. Wolfe, J. P.; Buchwald, S. L. Angew. Chem. Int. Ed. 1999, 38, 2413.
31. Wiley Registry 8th/NIST 2005 Mass Spectral Library; Wiley: New Jersey, 2006.
32. (a) King, L. A.; Poortman van der Meer, A. J. Sci. Justice 2001, 41, 200.
33. (b) Westphal, F.; Rösner, P.; Junge, Th. Forensic. Sci. Int. 2010, 194, 53.
34. Abbotto, A.; Alanzo, V.; Bradamante, S.; Pagani, G. A. J. Chem. Soc., Perkin Trans. 2 1991, 481.
35. Luke, R. W. A. US Patent US2006/0069109 A1, 2006.
36. Metzger, A.; Schade, M. A.; Knochel, P. Org. Lett. 2008, 10, 1107.
37. Unpublished results.
38. Minato, A.; Tamao, K.; Hayashi, T.; Suzuki, K.; Kumada, M. Tetrahedron Lett. 1980, 21, 845.
39. Berstein, J.; Stearns, B.; Shaw, E.; Lott, W. A. J. Am. Chem. Soc. 1947, 69, 1151.