Synthesis of new benzo[c]phenanthridine derivatives

Abstract

Synthesis of New Benzo[c]phenanthridineDerivatives. -Three component condensation of naphthylamine (I) with triethyl orthoformate and dimedone or reaction of amine (I) with 2-acetylcyclohexanedione deivatives (VI) affords corresponding enamino diketones (IV) and (VIII), resp., which undergo PPA-mediated intramolecular cyclizations to furnish new benzophenanthridine derivatives in good yields. Attempted intramolecular cyclization of enamino diketone (X) derived from cyclopentanedione (IX) fails. -(PYRKO, A. N.; Russ.

One-Pot Synthesis, E-/Z-Equilibrium in Solution of 3-Hetarylaminomethylidenefuran-2(3H)-ones and the Way to Selective Synthesis of the E-Enamines

“…In this way, various biologically active compounds can be made. Noncyclic compounds, the most common of which are cyclohexanedione derivatives [ 17 , 18 , 19 , 20 ], can act as carriers of the active methylene component [ 18 , 19 ]. Active methylene heterocyclic compounds [ 21 ] with different ring sizes and heterocycles containing a methyl group in the side chain [ 22 , 23 ] are widely used.…”

Fabrication of Nano‐CuO@ZnO for the Synthesis of Functionalized β‐Enaminone Derivatives from β‐Nitrostyrenes, Aliphatic/Aromatic Amines and 1,3‐Dicarbonyl/4‐Hydroxy Coumarin

“…Traditionally, β ‐enaminones were synthesized by the reaction of cyclic 1,3‐diketones, triethyl orthoformate and amines, or via the nucleophilic addition of the triketones with primary or secondary amines…”

“…Traditionally, b-enaminones were synthesized by the reaction of cyclic 1,3-diketones, triethyl orthoformate and amines, [5] or via the nucleophilic addition of the triketones with primary or secondary amines. [6] The condensation of active methylene compounds and ketones in presence of dimethoxy-N,N-dimethylmethanamine was also adopted to prepare these moieties.…”

Three-component reaction between substituted β-nitrostyrenes, β-dicarbonyl compounds and amines: diversity-oriented synthesis of novel β-enaminones

“…4 This combination of significant pharmacological and biological properties and compelling synthetic utility has resulted in the development of a number of methods for enamino diketone preparation. They are most commonly synthesized either by enamination of the corresponding cyclic 1,3-diketone and triethyl orthoformate with aromatic amines, 5 or by direct nucleophilic addition of the triketones such as 2-benzoyl-1,3-cyclohexanedione with a primary or secondary amine. 6 In addition, the condensation of methylketones or ketones with activated methylene and dimethoxy-N,N-dimethylmethanamine was usually used to prepare the enaminones.…”