The Bohlmann-Rahtz route to functionalised pyridine scaffolds and their use in library synthesis

Tetrahedron Letters

Volumn 44, Issue 8, 2003, Pages 1627-1629

  Bashford, Katherine E ^a   Burton, Matthew B ^b   Cameron, Stuart ^b   Cooper, Anthony L ^b   Hogg, Rebecca D ^b   Kane, Peter D ^b   MacManus, David A ^b   Matrunola, Christopher A ^b   Moody, Christopher J ^a   Robertson, Avril A B ^b   Warne, Mark R ^b  

^a UNIVERSITY OF EXETER   (United Kingdom)

^b Tripos Receptor Research Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

NICOTINIC ACID DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 0037450398     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00034-0     Document Type: Article

References (24)

1. Gilchrist T.L. J. Chem. Soc., Perkin Trans. 1. 1999;2849-2866.
2. Gilchrist T.L. J. Chem. Soc., Perkin Trans. 1. 2001;2491-2515.
3. Groutas W.C., Kuang R.Z., Ruan S.M., Epp J.B., Venkataraman R., Truong T.M. Bioorg. Med. Chem. 6:1998;661-671.
4. Ding S., Gray N.S., Wu X., Ding Q., Schultz P.G. J. Am. Chem. Soc. 124:2002;1594-1596.
5. Bouras A., Boggetto N., Benatalah Z., de Rosny E., Sicsic S., Reboud-Ravaux M. J. Med. Chem. 42:1999;957-962.
6. Phillips G., Davey D.D., Eagen K.A., Koovakkat S.E., Liang A., Ng H.P., Pinkerton M., Trinh L., Whitlow M., Beatty A.M., Morrissey M.M. J. Med. Chem. 42:1999;1749-1756.
7. Bohlmann F., Rahtz D. Chem. Ber. 90:1957;2265-2272.
8. Moody C.J., Bagley M.C. Synlett. 1998;361-362.
9. Bagley M.C., Bashford K.E., Hesketh C.L., Moody C.J. J. Am. Chem. Soc. 122:2000;3301-3313.
10. Adlington R.M., Baldwin J.E., Catterick D., Pritchard G.J., Tang L.T. J. Chem. Soc., Perkin Trans. 1. 2000;303-305.
11. Adlington R.M., Baldwin J.E., Catterick D., Pritchard G.J., Tang L.T. J. Chem. Soc., Perkin Trans. 1. 2000;2311-2316.
12. Bagley M.C., Dale J.W., Bower J. Synlett. 2001;1149-1151.
13. Bagley M.C., Dale J.W., Hughes D.D., Ohnesorge M., Phillips N.G., Bower J. Synlett. 2001;1523-1526.
14. Bagley M.C., Brace C., Dale J.W., Ohnesorge M., Phillips N.G., Xiong X., Bower J. J. Chem. Soc., Perkin Trans. 1. 2002;1663-1671.
15. Bagley M.C., Dale J.W., Bower J. Chem. Commun. 2002;1682-1683.
16. Bagley M.C., Lunn R., Xiong X. Tetrahedron Lett. 43:2002;8331-8334.
17. Bagley M.C., Dale J.W., Ohnesorge M., Xiong X., Bower J. J. Comb. Chem. 5:2003;41-44.
18. Oikawa Y., Sugano K., Yonemitsu O. J. Org. Chem. 43:1978;2087-2088.
19. ChemSpace™ and ChemCore™ are Tripos' proprietary library-design technology and cheminformatics solution providing critical tracking of the chemistry process inside the laboratory.
20. Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. Adv. Drug Deliv. Rev. 23:1997;3-25.
21. Cramer R.D., Poss M.A., Hermsmeier M.A., Caulfield T.J., Kowala M.C., Valentine M.T. J. Med. Chem. 42:1999;3919-3933.
22. Clark R.D., Patterson D.E., Soltanshahi F., Blake J.F., Matthew J.B. J. Mol. Graphics Mod. 18:2000;404-411.
23. Clark R.D.J. Chem. Inf. Comput. Sci. 37:1997;1181-1188.
24. 1 intermediates: 4-(imidazol-1-yl)aniline; 1,2,5,6-tetrahydropyridine; thiazolidine; ethyl piperazine-1-carboxylate; 3-(2-aminoethyl)indole; 2-amino-5-(tert-butyl)-1,3,4-thiadiazole; N-methylfurfurylamine; 2-(2-aminoethyl)thiophene; 2-ethoxybenzylamine; isoindoline; 2-N-propoxyethylamine; 1-(3-aminopropyl)imidazole; 3-(aminomethyl)pyridine; 2-(furfurylthio)ethylamine.