Reactivity of 4-hydroxy-2-methyl-7,8,9,10-tetrahydrobenzo[h] quinoline towards base-catalyzed cyclization,mannich and turpin reactions |
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Authors: | M Abbasi M Nasr H H Zoorob J M Michael |
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Abstract: | Mannich reaction upon 4-hydroxy-2-methyl-7,8,9,10-tetrahydrobenzoh]quinoline ( 1 ) as well as 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. Also, Turpin's reaction gave the benzoquinobenzoxazines 7a-d when applied to 6b . Treatment of 6f, 6g with alkali and the condensation of 6b with glycine in alcoholic sodium carbonate solution afforded the imidazo4,5-c]quinoline derivatives 9a-c , respectively. |
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