exo-2,3-Epoxybicyclo[2.2.1]heptan-endo-5,6-dicarboximides: versatile starting materials for the preparation of oxazaheterocyclic cage compounds

Grignard Reagents and Their N‐analogues in the Synthesis of Tricyclic and Tetracyclic Cage‐like Lactams

“…The structures of synthesized heterocycles 11a – s were confirmed by their IR and 1 H NMR and 13 C NMR spectra. Key signals in the 1 H NMR spectra of new compounds are singlet and doublet ( 3 J 3,10 3.4–5.1 Hz) of the trans ‐oriented protons H 2 and H 3 (3.25–3.89 and 3.92–4.42 ppm) in norbornane subunit . Resonance of methylene protons in ethyl group is notable in spectra of compounds 11b – h .…”

“…Recently, we have developed the synthesis of N ‐substituted tetracyclic lactams 9 (Fig. ) belonging to the most rare group of represented polycycles (substructure 2 ; Fig.…”

“…Cage compounds are characterized by three‐dimensional structures that have defined rigid geometry, and as such, they are very useful synthons in organic synthesis, as well as the indispensable substrates for the mechanistic studies . The synthesis and chemistry of polycyclic cage‐like heterocycles derived from exo ‐epoxynorbornanes 1 has attracted considerable attention in recent years from both our group and many others (Fig. ).…”

The formation of the salt and neutral molecule cocrystal from equimolar solution of heliamine and bicyclo[2.2.1]hept-5-ene-endo-2,3-dicarboxylic acid

“…The bicyclo[2.2.1]hept-5-ene-endo-2,3-dicarboxylic acid anhydride is used widely as an initial compound for the synthesis of amido acids possessing prominent biological properties (Kas'yan et al, 2005(Kas'yan et al, , 2006aPalchikov et al, 2014;Klimochkin et al, 2015;Zhang & Mastalerz, 2014). Among these derivatives were found analgesics (Palchikov et al, 2011), tranquillizer (Koch et al, 1971), anticonvulsant and antihypoxic (Palchikov et al, 2011) agents.…”

Reactivity of 5-endo-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-en-3-ones and their isomerization initiated by acids and bases

“…This study is a continuation of our research in the field of reactivity of cage imides [15][16][17][18] aimed at the preparation from these substances of various azaheterocycles and their functional derivatives [19,20]. We report here on the investigation of isomerization of 5-hydroxy-pyrrolidin-2-ones (hydroxylactams), derivatives of imides of bicyclo[2.2.1]hept-5ene-endo,endo-2,3-dicarboxylic acid.…”