AN EASY PHOTOCHEMICAL APPROACH TO THE SYNTHESIS OF THE FOOD-BORNE CARCINOGEN 2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE

Citation
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
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404039
Volume
38
Issue
44
Year of publication
1997
Pages
7793 - 7796
Database
ISI
SICI code
0040-4039(1997)38:44<7793:AEPATT>2.0.ZU;2-R
Abstract
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.