Fs. Bavetta et al., AN EASY PHOTOCHEMICAL APPROACH TO THE SYNTHESIS OF THE FOOD-BORNE CARCINOGEN 2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE, Tetrahedron letters, 38(44), 1997, pp. 7793-7796
Mutations induced by substances formed during food cooking are a field
of growing interest; for a better comprehension of the mechanism of a
ction of these carcinogens, simple routes to their synthesis are neede
d. In this letter we describe an easy method for 2-amino-1-methyl-6-ph
enylimidazo[4,5-b]py (PhIP) synthesis, starting from the commercially
available 2,3-diaminopyridine 1 via the 2-amino-3-methylamino-5-phenyl
pyridine 5 formation. The key step of this approach is the one pot syn
thesis of 5 performed by photolysis of 2-amino-5-iodo-3-(N-methyl-N-to
sylamino)pyridine 4 to obtain simultaneous phenylation and tosyl group
removal. Compound 5 was then used as an intermediate to obtain the 1-
methyl-6-phenylimidazo[4,5-b]pyridine 6 which was aminated to afford P
hIP in good overall yields. (C) 1997 Elsevier Science Ltd.