A convenient method is reported for the synthesis of 34 novel tricyclic and tetracyclic cage‐like lactams in high to excellent yields. The method involves treatment of easily available exo‐2,3‐epoxy(or Ts‐aziridino)bicyclo[2.2.1]heptan‐endo‐5,6‐dicarboximides by Grignard reagents, their N‐analogues, or phenyl lithium in tetrahydrofuran. In silico screening of biological activity spectrum showed high probability levels of glyceryl‐ether monooxygenase inhibitory, testosterone 17β‐dehydrogenase (NADP+) inhibitory, bilirubin oxidase inhibitory, and anti‐ischemic activity for tetracyclic derivatives.

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Study of isomerization of 5-endo-hydroxy-4-azatricyclo[5.2.1.0 2,6 ]dec-8-en-3-ones under the action of Lewis acids (MgBr 2 , AlCl 3 ), CF 3 COOH, and NaH showed that the optimum catalyst of the process was trifluoroacetic acid. In reaction of 4-benzyl-5-endo-hydroxy-4-azatricyclo-[5.2.1.0 2,6 ]dec-8-en-3-one with anhydrous AlCl 3 in benzene was unexpectedly isolated N-benzyl-3-(diphenylmethyl)bicyclo[2.2.1]hept-5-ene-2-carboxamide. A convenient method was developed for the preparation of 5-exo-alkoxy-4-alkyl(aryl)-4azatricyclo[5.2.1.0 2,6 ]dec-8-en-3-ones.