Reaction of arene oxides with nucleosides.

Inosine was reacted with phenanthrene-9,10-oxide and 7,12-dimethylbenz(a)anthracene-5,6-oxide (DMBA-5,6-oxide) to yield the corresponding N-1-alkylinosines. They were shown to undergo hydrolysis to 5-amino-4-imidazole-N-alkylcarboxamide ribosides when heated in the presence of sodium carbonate. Guanosine was reacted with DMBA-5,6-oxide to yield a mixture of N-7-alkylguanines along with a smaller amount of an orcine positive product exhibiting an ultraviolet spectrum resembling that of DMBA-5,6-dihydrodiol.