One-Pot Esterification and Amide Formation via Acid-Catalyzed Dehydration and Ritter Reactions

Abstract

General Remarks1 H NMR spectra were recorded at 300 or 400 MHz with CDCl3 as solvent. 13 C-NMR spectra were obtained at 75.4 or 100.59 MHz in CDCl 3 . Chemical shifts were determined relative to the residual solvent peaks (CHCl3, δ = 7.26 ppm for hydrogen atoms, δ = 77.0 for carbon atoms).

An efficient and general method for the synthesis of stable isotope deuterium labeled phthalate esters

“…The manufacture of phthalate esters is fairly common in industrial scale. The most common method for the preparation of phthalate esters is the esterification of phthalic anhydride or phthalic acid generally catalyzed by acids and refluxed for several hours 22–25 . However, the reaction conditions of strong acid catalysis and high temperature reflux are not suitable for deuterium labeled synthesis, which will lead to the decrease of product abundance.…”

Synthesis and styrene copolymerization of novel dimethyl and dimethoxy ring-substituted isobutyl phenylcyanoacrylates

“…Dimethyl ring-substituted phenylcyanoacrylates (PCA) are reported in a number of applications [1][2][3][4][5][6][7][8][9][10][11][12]. Thus, 2,3-dimethyl-phenyl ethyl PCA was prepared inside microflow reactor using polymer networks carrying tertiary amine as a catalyst [1], whereas 3,4dimethyl-phenyl PCA was prepared with amine-functionalized polyacrylonitrile fiber [2].…”

“…2,3-Dimethoxy ring-disubstituted ethyl PCA used in synthesis of pyranoquinoline [6], of polysubstituted cyclopropanes [7], of some derivatives of o-vanillin [8], as well as in microwave enhanced Knoevenagel condensation of ethyl cyanoacetate with aldehydes [9]. 3,4-Dimethoxy-phenyl ring-disubstituted isobutyl PCA was reported in esterification and amide formation via acid-catalyzed dehydration and Ritter reactions [10]. 3,5-Dimethoxy-phenyl methyl PCA was used in synthesis of pyrido [2,1-c]-1,2,4-triazine, 1,2, 4-triazolo[4,3-a]pyridine and 2-(substituted-pyrazolyl)nicotinonitrile [11] and in synthesis of dihydrouracils spiro-fused to pyrrolidines [12].…”

Synthesis and styrene copolymerization of novel dimethyl and dimethoxy ring-substituted isobutyl phenylcyanoacrylates

“…where R is 2,3-dimethyl, 2,4-dimethyl, 3,5-dimethyl, 2,3-dimethoxy, 2,4-dimethoxy, 2,5dimethoxy, 2,6-dimethoxy, 3,4-dimethoxy, 3,5-dimethoxy, and explored the feasibility of their copolymerization with styrene. To the best of our knowledge, there have been no reports (except 3,4-dimethoxy [30]) on either synthesis of these compounds, nor their copolymerization with styrene.…”