The palladium-catalyzed cross-coupling reactions of 3-chloro-4-halogeno-1,2,5-thiadiazoles

Heterocycles

Volumn 60, Issue 1, 2003, Pages 29-45

  Merschaert, Alain ^a   Gorissen, Hugo J ^a  

^a Eli Lilly Benelux   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

3 BROMO 4 CHLORO 1,2,5 THIADIAZOLE; 3 CHLORO 4 IODO 1,2,5 THIADIAZOLE; 3,4 DICHLORO 1,2,5 THIADIAZOLE; BORONIC ACID DERIVATIVE; HALOGENATED HYDROCARBON; HETEROCYCLIC COMPOUND; PALLADIUM; THIADIAZOLE DERIVATIVE; TIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; DESULFURIZATION; HALOGENATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0037246811     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-02-9550     Document Type: Article

References (26)

1. Y. Hanasaki, H. Watanabe, K. Katsuura, H. Takayama, S. Shirakawa, K. Yamaguchi, S. Sakai, K. Ijichi, M. Fujiwara, K. Konno, T. Yokota, S. Shigeta, and M. Baba, J. Med. Chem., 1995, 38, 2038. See also references cited in this paper.
2. For the [4+1] approach (N-C-C-N/S): see (a) L. M. Weinstock, P. Davis, B. Handelsman, and R. J. Tull, J. Org. Chem., 1967, 32, 2823. For the [3+2] approach (C-C-N/N-S): see (b) S. C. Yoon, J. Cho, and K. Kim, J. Chem. Soc., Perkin Trans. I, 1998, 109. For the [2+3] approach (C-C/N-S-N): see (c) L. M. Weinstock and I. Shinkai, "1,2,5-Thiadiazoles and Their Benzo Derivatives" in "Comprehensive Heterocyclic Chemistry", ed. by A. R. Katritzky, C. W. Rees and K. T. Potts, Pergamon Press, Oxford, 1984, Vol. 6, p. 513.
3. For the [4+1] approach (N-C-C-N/S): see (a) L. M. Weinstock, P. Davis, B. Handelsman, and R. J. Tull, J. Org. Chem., 1967, 32, 2823. For the [3+2] approach (C-C-N/N-S): see (b) S. C. Yoon, J. Cho, and K. Kim, J. Chem. Soc., Perkin Trans. I, 1998, 109. For the [2+3] approach (C-C/N-S-N): see (c) L. M. Weinstock and I. Shinkai, "1,2,5-Thiadiazoles and Their Benzo Derivatives" in "Comprehensive Heterocyclic Chemistry", ed. by A. R. Katritzky, C. W. Rees and K. T. Potts, Pergamon Press, Oxford, 1984, Vol. 6, p. 513.
4. For the [4+1] approach (N-C-C-N/S): see (a) L. M. Weinstock, P. Davis, B. Handelsman, and R. J. Tull, J. Org. Chem., 1967, 32, 2823. For the [3+2] approach (C-C-N/N-S): see (b) S. C. Yoon, J. Cho, and K. Kim, J. Chem. Soc., Perkin Trans. I, 1998, 109. For the [2+3] approach (C-C/N-S-N): see (c) L. M. Weinstock and I. Shinkai, "1,2,5-Thiadiazoles and Their Benzo Derivatives" in "Comprehensive Heterocyclic Chemistry", ed. by A. R. Katritzky, C. W. Rees and K. T. Potts, Pergamon Press, Oxford, 1984, Vol. 6, p. 513.
5. Y. Hanasaki, Heterocycles, 1996, 43, 2435.
6. A. Merschaert and R. L. Robey, Eli Lilly & Co., "Palladium-catalyzed cross-coupling chemistry on 3-chloro-4-halogeno-1,2,5-thiadiazole", US Application 09/370957, 1998.
7. J.K. Stille, Angew. Chem. Int. Ed. Engl., 1986, 25, 508.
8. A. Suzuki, Pure & Appl. Chem., 1994, 66, 213.
9. Both 3-bromo-4-chloro- and 3-chloro-4-iodo-1,2,5-thiadiazole are not reported in the current literature yet. Only the 3-chloro-4-fluoro-1,2,5-thiadiazole is reported as occurring into a mixture (mono- and difluorinated 1,2,5-thiadiazoles) resulting from the reaction of potassium fluoride on the 3,4-dichloro-1,2,5-thiadiazole in sulfolane: see M. Geisel and R. Mews, Chem. Ber., 1982, 115, 2135.
10. Formation of 3,4-diamino-1,2,5-thiadiazole: see (a) A.P. Komin and M. Carmack, J Heterocycl. Chem., 1976, 13, 13. Formation of 3,4-bis(2-(trimethylsilyl)ethynyl)-1,2,5-thiadiazole: see (b) J. Kouvetakis, D. Grotjahn, P. Becker, S. Moore, and R. Dupon, Chem. Mater., 1994, 6, 636.
11. Formation of 3,4-diamino-1,2,5-thiadiazole: see (a) A.P. Komin and M. Carmack, J Heterocycl. Chem., 1976, 13, 13. Formation of 3,4-bis(2-(trimethylsilyl)ethynyl)-1,2,5-thiadiazole: see (b) J. Kouvetakis, D. Grotjahn, P. Becker, S. Moore, and R. Dupon, Chem. Mater., 1994, 6, 636.
12. L. M. Weinstock, D. M. Mulvey, and R. Tull, J. Org. Chem., 1976, 41, 3121.
13. A. Merschaert, "Réactivité des 3,4-dihalogéno-1,2,5-thiadiazoles. Application au 3,4-dichloro-1,2,5-thiadiazole de la réaction de couplage croisé catalysée par les métaux de transition.", Dissertation, Free University of Brussels, 1998.
14. A sample of 3-chloro-4-phenyl-1,2,5-thiadiazole was prepared by cyclization reaction of α-amino-α-phenylacetonitrile with sulfur monochloride: see reference 2a.
15. The 3,4-diphenyl-1,2,5-thiadiazole was prepared by Pd-catalyzed cross-coupling reaction of 3-chloro-4-phenyl-1,2,5-thiadiazole with tributylphenyl stannane under the Stille conditions reported in reference 3.
16. Occurrence of minor degradations via pathway 2b is also suggested in reference 3.
17. According to the nomenclature the 3- and 4-position are ranked by alphabetic order. For example: 3-chloro-4-vinyl-vs. 3-allyl-4-chloro-1,2,5-thiadiazole.
18. 4 was found to be effective: see reference 10.
19. Synthesis of 3-chloro-4-(pyrid-3-yl)-1,2,5-thiadiazole is reported by cyclization of the Strecker adduct of pyridine-3-carboxaldehyde with sulfur monochloride: see P. Sauerberg, P. H. Olesen, S. Nielsen, S. Treppendahl, M. J. Sheardown, T. Honoré, C. H. Mitch, J. S. Ward, A. J. Pike, F. B. Bymaster, B. D. Sawyer, and U. H. E. Shannon, J. Med. Chem., 1992, 35, 2274.
20. 3-Pyridylboronic acid was prepared by reaction of 3-pyridylmagnesium bromide on a trialkylborate: see F. C. Fischer and E. Havinga, Rec. Trav. Chim. Pays-Bas, 1965, 84, 439; ibid., 1974, 93, 21.
21. 3-Pyridylboronic acid was prepared by reaction of 3-pyridylmagnesium bromide on a trialkylborate: see F. C. Fischer and E. Havinga, Rec. Trav. Chim. Pays-Bas, 1965, 84, 439; ibid., 1974, 93, 21.
22. Screening trials involving other catalyst, base and solvent conditions were found to be ineffective: see reference 10.
23. Preparation of 3-amino-4-chloro-1,2,5-thiadiazole: see reference 2a. See also the next patent applications: K. Menzl, Lentia GmbH, "Verfahren zur Herstellung von 1,2,5-Thiadiazolderivaten", DE 1175683, 1962 (Chem. Abstr., 1964, 61, 69177); Oesterreichische Stickstoffwerke AG, "Nouvelle sulfonamide et procédé pour sa préparation", BE 629551, 1963 (Chem. Abstr., 1963, 60, 90900).
24. Preparation of 3-amino-4-chloro-1,2,5-thiadiazole: see reference 2a. See also the next patent applications: K. Menzl, Lentia GmbH, "Verfahren zur Herstellung von 1,2,5-Thiadiazolderivaten", DE 1175683, 1962 (Chem. Abstr., 1964, 61, 69177); Oesterreichische Stickstoffwerke AG, "Nouvelle sulfonamide et procédé pour sa préparation", BE 629551, 1963 (Chem. Abstr., 1963, 60, 90900).
25. M. P. Doyle, B. Siegfried, and J. F. Dellaria, Jr., J. Org. Chem., 1977, 42, 2426.
26. C. A. Alt, L. Merritt, G. A. Rhodes, R. L. Robey, E. E. Van Meter, J. S. Ward, and C. H. Mitch, Eli Lilly & Co., "Preparation of 1,2,5-thiadiazoles as CNS agents", Eur. Pat. Appl., 0709381, 1996 (Chem. Abstr., 1996, 125, 86647).