Abstract
Quinoline N-oxide was treated with 1H-pyrrole in the presence of acetic anhydride to give 2-(2 [1H] pyrrolyl) quinoline (Ib) in 37.4% yield. In the reaction of Ib and 2-chloroethyl tosylate (V) in acetone catalyzed by potassium hydroxide, 2-(1-(2-tosyloxyethyl)-2 [1H]-pyrrolyl) quinoline (Ic) was obtained. Ic was unstable and cyclized gradually to a quaternary tosylate (VIa), which was reduced with sodium borohydride in methanol to 9, 13-diazagona-1, 3, 5 (10), 14, 16-pentaene (VII), which was identified as its picrolonate.
