Chemo and regioselective serendipitous electrochemically initiated spirocyclization of caffeic acid esters with barbituric acid derivatives

Abstract

Please cite this article as: Abdolhamid Alizadeh, Mohammad Mehdi Khodaei, Mitra Fakhari, Gisya Abdi, Sohrab Ghouzivand, Chemo and regioselective serendipitous electrochemically initiated spirocyclization of caffeic acid esters with barbituric acid derivatives, Electrochimica Acta http://dx. Abstract HOGraphite + R 1 = H or CH 3 R = Methyl or Ethyle or Isopropyl 1 2 6 I or II 2H + , 2e -An interesting sequence of oxidation/Michael addition/oxidation/spirocyclization is observed in the electrolysis of caffeic acid esters in the presence of barbituric acid derivatives leading to the synthesis of a series of novel spirocycles. In an experimentally simple and clean procedure, the electrolyses proceed via a domino of electrochemical (E) and chemical (C) events with employing electrons as the only reagents in aqueous solution without introducing any catalyst or oxidant. From mechanistic point of view, a new type of domino mechanism (ECEC i , C i =spirocyclization) is proven with a unique C i phenomenon at final step. Also, in light of experimental and theoretical NMR investigations, highly chemo and regioselectivities have been detected in these synthetic electrolyses.

A review of the synthetic strategies toward spirobarbiturate-fused 3- to 7-membered rings

“…It should be noted that the synthesized compounds showed antibacterial activity against Gram-positive and Gram-negative bacterial strains (Scheme 42). 85…”

Guanylguanidines: Catalyst and Ligand for Organic Transformations

“…Alizadeh et al [73] in 2015 explored the catalytic application of immobilized metformin on SBA-15 (SBA-15/Met3, C13) and magnetically separable silica (Fe 3 O 4 /SiO 2 /Met, C15) for Henry reaction. The catalyst was found to be efficient under mild conditions.…”