Examination of the mechanism of the intramolecular amination of N-(3-bromopyridin-2-yl)azaheteroarylamines and N-(2-chloropyridin-3-yl)azaheteroarylamines: a Pd-catalyzed amination and/or a base-assisted nucleophilic aromatic substitution?

Tetrahedron

Volumn 63, Issue 18, 2007, Pages 3818-3825

  Loones, Kristof T J ^a   Maes, Bert U W ^a   Herrebout, Wouter A ^a   Dommisse, Roger A ^a   Lemière, Guy L F ^a   Van der Veken, Benjamin J ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

Aromaticity; Buchwald Hartwig reaction; SNAr; Tautomers

Indexed keywords

2 CHLORO 3 IODOPYRIDINE; AROMATIC AMINE; PALLADIUM; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; RING CLOSING METATHESIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33947641657     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.041     Document Type: Article

References (26)

1. Sugimura T. Mutat. Res. 376 (1997) 211-219
2. Kataoka H. J. Chromatogr., A 774 (1997) 121-142
3. Toribio F., Moyano E., Puignou L., and Galceran M.T. J. Chromatogr., A 948 (2002) 267-281
4. Wakabayashi K., and Sugimura T. J. Nutr. Biochem. 9 (1998) 604-612
5. Takeda K., Shudo K., Okamoto T., and Kosuge T. Chem. Pharm. Bull. 26 (1978) 2924-2925
6. Novak M., Toth K., Rajagopal S., Brooks M., Hott L.L., and Moslener M. J. Am. Chem. Soc. 124 (2002) 7972-7981
7. Hashimoto Y., Shudo K., and Okamoto T. J. Am. Chem. Soc. 104 (1982) 7636-7640
8. Weisburger J.H. Nutrition 16 (2000) 767-773
9. Imamura M., Takeda K., Shudo K., Okamoto T., Nagata C., and Kodama M. Biochem. Biophys. Res. Commun. 96 (1980) 611-617
10. Guram A.S., Rennels R.A., and Buchwald S.L. Angew. Chem., Int. Ed. Engl. 34 (1995) 1348-1350
11. Louie J., and Hartwig J.F. Tetrahedron Lett. 36 (1995) 3609-3612
12. Hartwig J.F. Synlett (2006) 1283-1294
13. Littke A.F., and Fu G.C. Angew. Chem., Int. Ed. 41 (2002) 4176-4211
14. Schlummer B., and Scholz U. Adv. Synth. Catal. 346 (2004) 1599-1626
15. Yang B.H., and Buchwald S.L. J. Organomet. Chem. 576 (1999) 125-146
16. Loones K.T.J., Maes B.U.W., Dommisse R.A., and Lemière G.L.F. Chem. Commun. (2004) 2466-2467
17. Loones K.T.J., Maes B.U.W., Meyers C., and Deruytter J. J. Org. Chem. 71 (2006) 260-264
18. NAr was published. The correct yield is 87%.
19. The N-(2-chloropyridin-3-yl)azaheteroarylamines are synthesized using the conditions for the synthesis of dipyrido[1,2-a:3′,2′-d]imidazole and its benzo and aza analogues (see Ref. 16), only the reaction time was shortened.
20. Bird C.W. Tetrahedron 53 (1997) 13111-13118
21. Cossi M., Rega N., Scalmani G., and Barone V. J. Chem. Phys. 114 (2001) 5691-5701
22. Cossi M., Scalmani G., Rega N., and Barone V. J. Chem. Phys. 117 (2002) 43-54
23. McQuarrie D.A., and Simon J.D. Physical Chemistry: A Molecular Approach. 2nd ed. (1997), University Science Books, Sausalito
24. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Wallingford, CT
25. Turck A., Plé N., Ndzi B., Quéguiner G., Haider N., Schuller H., and Heinisch G. Tetrahedron 49 (1993) 599-606
26. The reaction conditions are not optimized.