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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This review summarizes a series of studies on the reactions of 1H-pyrrole-2,3-diones, fused at the C 5 -N 1 bond to nitrogen-containing heterocycles, with nucleophiles, leading to the formation of C-C bonds. Reactions of pyrrolobenzoxazinetrione and pyrroloquinoxalinetrione with CH,OH-, CH,NH-binucleophiles, and dienophiles are discussed.

[reaction: see text] 2-Polyfluoroalkylchromones react with 1,3,3-trimethyl-3,4-dihydroisoquinolines to give zwitterionic axially chiral 6,7-dihydrobenzo[a]quinolizinium derivatives in high yields. In addition, performing this reaction with aromatic methylketimines is a simple and convenient synthesis of 2,6-diaryl-4-polyfluoroalkylpyridines.