A method for rapid construction of indolo [3,2-l]acridin-7-one systems bearing isocryptolepine scaffold is described. Metalfree condensation of (4-methoxyphenyl)cyclohexan carbinols with ortho-amino/hydroxybenzonitriles in concentrated sulfuric acid yields polyannulated compounds with four new stereo-genic centers in a highly diastereoselective manner. The reaction includes elecrophilic dearomatization of methoxyarene, formation of spirocyclic intermediate and intramolecular 1,4-nucleophilic addition sequence.

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Reactions of available 1-alkyl-3,4-dihydroisoquinolines with 4-(2,2,2-trifluoroacetyl)-, 4-acetyl-or 4-(ethoxy-methylene)-2-aryloxazol-5(4H)-ones were studied. A series of new 3-amino-6,7dihydro-4H-pyrido[2,1-a]isoquinolin-4-one derivatives was synthesized. The intermediates formed as a result of the addition of azlactone to 1-methyl-3,4-dihydroisoquinoline were isolated. The effect of the nature of the substituents, as well as the reaction conditions on the yield and structure of the title products was revealed.

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