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An easy photochemical approach to the synthesis of the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine

✍ Scribed by Fabio S. Bavetta; Tullio Caronna; Massimo Pregnolato; Marco Terreni

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 166 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10039-9

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✦ Synopsis

Mutations induced by substances formed during food cooking are a field of growing interest; for a better comprehension of the mechanism of action of these carcinogens, simple routes to their synthesis are needed. In this letter we describe an easy method for 2-amino-l-methyl-6-phenylimidazo[4,5-b]pyridine (PhlP) synthesis, starting from the commercially available 2,3-di~mlnopyridine 1 via the 2-amino-3methylamino-5-phenylpyridine S formation. The key step of this approach is the one pot synthesis of 5 performed by photolysis of 2-amino-5-iodo-3-(N-methyi-N-tosylamlno)pyridine 4 to obtain simultaneous phenyiation 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 PhIP in good overall yields.

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