Ethyl 2-amino-4,6-bis(4-fluorophenyl)cyclohexa-1,3-diene-1-carboxylate

Abstract

Cyclohexenones are efficient synthons in building spiro compounds (Padmavathi, Sharmila, Somashekara Reddy & Bhaskar Reddy, 2001) or intermediates in the synthesis of benzisoxazoles or carbazole derivatives (Padmavathi et al., supporting information sup-8

Ethyl 2-amino-6-(4-bromophenyl)-4-(4-fluorophenyl)cyclohexa-1,3-diene-1-carboxylate

“…The title compound, (I), was prepared by the amination of cyclohexenone derivative of 4-bromo-4′-fluorochalcone with ammonium acetate. The crystal structure of a similar aminated product viz., ethyl 2-amino-4,6-bis (4-fluorophenyl)cyclohexa-1,3-diene-1-carboxylate has been reported (Jasinski et al, 2012). Also, the crystal structure of precursor of the title compound (I) viz., ethyl 6-(4-bromophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate has been reported (Kant et al, 2012).…”

“…For cyclohexenones as precursors for functionalized derivatives, see: Samshuddin et al (2013); For 4-bromo-4 0 -fluorochalcone derivatives, see: Fun et al (2012a,b,c). For related structures, see: Jasinski et al (2012); Kant et al (2012). For puckering parameters, see: Cremer & Pople (1975).…”

Synthesis, Characterization and Crystal Structure of Ethyl 2-amino-4-(4-fluorophenyl)-6-phenylcyclohexa-1,3-diene-1-carboxylate

“…The amination of cyclohexenone derivative of 1-(4-fluorophenyl)-3-phenylprop-2-en-1-one with ammonium acetate afforded the title compound (I). The crystal structure of similar aminated products viz., ethyl 2-amino-4,6-bis(4-fluoro phenyl)cyclohexa-1,3-diene-1-carboxylate and ethyl 2-amino-6-(4-bromophenyl)-4-(4-fluorophenyl)cyclohexa-1,3-diene-1-carboxylate have been reported [4,5]. The crystal structure of the cyclohexenone derivatives viz., ethyl 6-(4-bromophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate and ethyl 4,6-bis(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate have been reported [6,7].…”

Expected and Unexpected Products in Half Curcuminoid Synthesis: Crystal Structures of But-3-en-2-ones and 3-Methylcyclohex-2-enones

“…The prop-2-en-1-one moiety also provides a chemically reactive function for Michael-type additions [4][5][6][7][8], leading to the formation of cyclic structures through a domino reaction [9,10] (Scheme 1, Path II) in the presence of catalysts other than a strong base. Enones and cyclohexenones are the building blocks or synthons [10,11] important in the synthesis of natural products and a wide range of biological activities have been associated with them, such as anti-inflammatory and anticancer effects [12,13]. Furthermore, they are used as food additives and in the synthesis of pheromones [14].…”