| abstract |
2-HYDROXY - 3 - (3,3,5-TRIMETHYCLCYCLOHEXYL)-(CH2)N)1,4-NAPHTHOQUINONES WERE N IS AN INTEGER FROM 4 TO 12 INCLUSIVE, HAVING ANTIMALARIAL PROPERTIES, ARE PREPARED: (A) BY HEATING 2-HYDROXY-1,4-NAPHTHOQUINONE WITH A DIACYL PEROXIDE OF THE FORMULA (3,3,5-TRIMETHYLCYCLOHEXYL)(CH2)N-CO)2O2 WHERE N IS 4 TO 12 INCLUSIVE TO PRODUCE SAID NAPHTHOQUINONES WHERE N IF 4 TO 12, RESPECTIVELY; (B) BY OXIDIZING UNDER ALKALINE CONDITIONS 2-HYDROXY-3-(3,3, 5-TRIMETHYLCYCLOHEXYL)-(CH2)N) - 1,4 - NAPHTHOQUINONE WHERE N IS 5 TO 12 INCLUSIVE TO PRODUCE THE CORRESSPONDING COMPOUND WHERE N IS 4 TO 11, RESPECTIVELY; AND, (C) BY THE STEPS OF OXIDIZING 2-((3,3,5 - TRIMETHYLCYCLOHEXYL)CH2)N)-1-NAPHTHOL WHERE N IS 4 TO 12 INCLUSIVE TO FORM 2 - (3,3,5-TRIMETHYCYCLOHEXYL) - (CH2)0) - NAPHTHOQUINONE, REACTING THE LATTER WITH A PEROXIDE UNDER ALKALINE CONDITIONS TO FORM 2 - ((3,3,5 - TRIMETHYLCYCLOHEXYL)(CH2)N) - 1,4-NAPHTHOQUINONE-2,3-OXIDE AND HYDROLYZING THE 2,3-OXIDE UNDER ACIDIC CONDITIONS TO YEILD 2-HYDROXY3-((3,3,5-TRIMETHYLCYCLOHEXYL)-(CH2)N) - 1,4 - NAPHTHOQUINONE. NOVEL INTERMEDIATES INCLUDE COMPOUNDS OF THE FORMULA (3,3,5 - TRIMETHYLCYCLOHEXYL) - (CH2)C-COOH WHERE X IS AN INTEGER FROM 3 TO 12 INCLUSIVE. |