Greater variety in Groebke-Blackburn type 3-arylaminoimidazo[1,2-a]azines accessed via Pd-catalyzed arylation of a primary amine precursor

Tetrahedron Letters

Volumn 49, Issue 41, 2008, Pages 5990-5993

  Sandulenko, Yuri ^a   Komarov, Alexander ^a   Rufanov, Konstantin ^a   Krasavin, Mikhail ^a,b  

^a Chemical Diversity Research Institute   (Russian Federation)

^b TULA STATE LEV TOLSTOY PEDAGOGICAL UNIVERSITY   (Russian Federation)

Author keywords

Buchwald Hartwig reaction; Convertible isonitrile; Groebke Blackburn reaction; Walborsky reagent

Indexed keywords

2 AMINOPYRIDINE; 2 PHENYLIMIDAZO[1,2 ALPHA]PYRAZIN 3 AMINE; 2 PHENYLIMIDAZO[1,2 ALPHA]PYRIDIN 3 AMINE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; GROEBKE BLACKBURN REACTION;

EID: 50249091554     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.177     Document Type: Article

References (28)

1. Groebke K., Weber L., and Mehlin F. Synlett (1998) 661-663
2. Blackburn C., Guan B., Fleming P., Shiosaki K., and Tsai S. Tetrahedron Lett. 39 (1998) 3635-3638
3. Bienaymé H., and Bouzid K. Angew. Chem., Int. Ed. 37 (1998) 2234-2237
4. Krasavin M., Tsirulnikov S., Nikulnikov M., Kysil V., and Ivachtchenko A. Tetrahedron Lett. (2008) 10.1016/j.tetlet.2008.06.11
5. Examples of recent patents and patent applications related to the Groebke-Blackburn reaction: (a) Klein, M.; Gericke, R.; Beier, N.; Cezanne, B.; Tsaklakidis, C.; Mederski, W. German Patent DE 102006048728, 2008; Chem. Abstr. 2008, 148, 475292.
6. Muci, A.; Finer, J. T.; Morgan, B. P.; Russell, A. J.; Morgans, D. J., Jr. PCT Int. Appl. WO 2008016648 A2, 2008; Chem. Abstr. 2008, 148, 215052.
7. Mederski, W.; Beier, N.; Cezanne, B.; Gericke, R.; Klein, M.; Tsaklakidis, C. PCT Int. Appl. WO 2007147478 A1, 2007; Chem. Abstr. 2008, 148, 100605.
8. Thormann, M. German Patent DE 102005019181, 2006; Chem. Abstr. 2006, 145, 471525.
9. For recent examples of isocyanide-based reactions of 2-aminoazines and -azoles see:. Rousseau A.L., Matlaba P., and Parkinson C.J. Tetrahedron Lett. 48 (2007) 4079-4082
10. Shaabani A., Soleimani E., and Maleki A. Tetrahedron Lett. 47 (2006) 3031-3034
11. DiMauro E.F., and Kennedy J.M. J. Org. Chem. 72 (2007) 1013-1016
12. Kercher T., Rao C., Bencsik J.R., and Josey J.A. J. Comb. Chem. 9 (2007) 1177-1187
13. Carballares S., Cifuentes M.M., and Stephenson G.A. Tetrahedron Lett. 48 (2007) 2041-2045
14. Umkehrer M., Ross G., Jäger N., Burdack C., Kolb J., Hu H., Alvim-Gaston M., and Hulme C. Tetrahedron Lett. 48 (2007) 2213-2216
15. Shaabani A., Maleki A., Moghimi R.J., and Soleimani E. Chem. Pharm. Bull. 55 (2007) 957-958
16. Adib M., Mahdavi M., Noghani M.A., and Mirzaei P. Tetrahedron Lett. 48 (2007) 7263-7265
17. Parchinsky V.Z., Shuvalova O., Ushakova O., Kravchenko D.V., and Krasavin M. Tetrahedron Lett. 47 (2006) 947-951
18. Krasavin M., and Parchinsky V. Synlett (2008) 645-648
19. Blackburn C., and Guan B. Tetrahedron Lett. 41 (2000) 1495-1500
20. For key reviews on the Buchwald-Hartwig reaction see:. Buchwald S.L., Mauger C., Mignani G., and Scholz U. Adv. Synth. Catal. 348 (2006) 23-39
21. Yang B.H., and Buchwald S.L. J. Organomet. Chem. 576 (1999) 125-146
22. Wolfe J.P., Wagaw S., Marcoux J.-F., and Buchwald S.L. Acc. Chem. Res. 31 (1998) 805-818
23. Walborsky H.M., and Niznik G.E. J. Am. Chem. Soc. 91 (1969) 7778-7780
24. Walborsky H.M., and Niznik G.E. J. Org. Chem. 37 (1972) 187-191
25. Under traditional conditions (methanol, Brønsted or Lewis acid catalyst), the Groebke-Blackburn reaction has been noted to lead also to regioisomeric 2-amino-3-phenylimidazo[1,2-a]azines:. Mandair G.S., Light M., Russell A., Hursthouse M., and Bradley M. Tetrahedron Lett. 43 (2002) 4267-4269
26. Ref. 6e.
27. 6: C, 66.66; H, 4.20; N, 29.15. Found: C, 66.65; H, 4.21; N, 29.17.
28. In a control experiment, arylation of 1a was attempted with 2-chloropyrazine in the absence of the palladium catalyst which resulted in virtually no conversion (as evidenced by LCMS analysis of the reaction mixture).