REACTIVITY OF 4-HYDROXY-2-METHYL-7,8,9,10-TETRAHYDROBENZO[H] QUINOLINE TOWARDS BASE-CATALYZED CYCLIZATION, MANNICH AND TURPIN REACTIONS

Mannich reaction upon 4-hydroxy-2-methyl-7,8,9,10-tetrahydrobenzo[h]quinoline and its nitration were studied. Condensation of the chloroquinoline 6b with sodium azide, benzylamine and ethanolamine gave the quinoline derivatives 6c, 6f and 6g, respectively. Phenylhydrazine and sodium borohydride effected reduction of the azidoquinoline 6c to the corresponding amino- and hydroxyamino derivatives 6d and 6e, respectively. Turpin''s reaction gave benzoquinobenzoxazines when applied to 6b. Treatment of 6f, 6g with alkali and the condensation of 6b with glycine in alcoholic sodium carbonate solution afforded imidazo[4,5-c]quinoline derivatives.