Transformations of 8-azabicyclo [3-2-1] octenones into 4-and 5-methylpyridin-3-ol and indole-tropane derivative

ABSTRACT

8-[substituted]-2-oxo-8-azabicyclo [3.2.1]-oct-3-ene derivatives Ia and Ib reacted with di-azomethane to give the corresponding two regioisomers of delta 2-pyrazoline derivatives II and III which were transformed directly into 4- and 5-methylpyridin-3-ols on pyrolysis. The synthesized 8-[2-cyanoethyl-8-azabicyclo [3.2.1] octan-6-exocarbonitrile-2-phenylhydrazone VIIa was treated with trifluoromethanesulfonic acid to yield the indole. derivative VIII