Thermal-Induced Dimerization Cyclization of Ethyl N-(Styrylcarbamoyl)acetates: Formation of 4-Hydroxy-2(1H)-pyridone-3- carboxamide Derivatives

Abstract

Table of contents General informationSynthesis and spectral data of (E)-diethyl 2-(styrylcarbamoyl)malonates S2Synthesis and spectral data of (E)-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamides S3Synthesis and spectral data of Ethyl 4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylates S4Synthesis and spectral data of (E)-ethyl 2-((E)-styrylcarbamoyl)-3-hydroxybut-2-enoates S6Synthesis and spectral data of 3-acetyl-4-hydroxypyridin-2(1H)-ones S71 H NMR and 13 C NMR spectra of (E)-diethyl 2-(styrylcarbamoyl)malonates S71 H NMR and 13 C NMR spectra of (E)-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamides S111 H NMR and 13 C NMR spectra of Ethyl 4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylates S151 H NMR and 13 C NMR spectra of (E)-ethyl 2-((E)-styrylcarbamoyl)-3-hydroxybut-2-enoates S181 H NMR and 13 C NMR spectra of 3-acetyl-4-hydroxypyridin-2(1H)-ones S20 X-ray crystallographic data for compound ethyl 2-(((E)-4-methoxystyryl)carbamoyl)-3-hydroxybut-2-enoate S22 s1 General informationMelting points were determined with RY-1 apparatus, and were uncorrected. IR spectra were determined as KBr pellets on a Shimadzu model 470 spectrophotometer. 1 H NMR spectra were recorded using a Bruker AV 400 MHz spectrometer in DMSO-d 6 and CDCl 3 with tetramethylsilane as internal standard. EI mass spectra were recorded on Shimadzu QP-2010 GC-MS system and Waters Micromass GCT system. ESI mass spectra were obtained on Shimadzu 2010A LC-MS instrument. Crystal structure was determined by using a Bruker SMART CCD area detector diffractometer. All chemicals and reagents were purchased from known commercial suppliers and were used without further purification. (E)-diethyl 2-(styrylcarbamoyl)malonate were synthesized according to the literature procedures with minor change [10] . Synthesis and spectral data of (E)-diethyl 2-(styrylcarbamoyl)malonatesGeneral procedure for the preparation of (E)-diethyl 2-(styrylcarbamoyl)malonate 5. To a ice-cooled solution of cinnamic acid (10.0 g, 67.6 mmol) in 100 mL toluene was added triethylamine (10.3 mL, 74.7 mmol) and diphenyl phosphorazidate (DPPA, 18.6 g, 67.6 mmol).

Revisiting Acetoacetyl Chemistry to Build Malleable Cross-Linked Polymer Networks via Transamidation

“…This preferred result can be attributed to three probable reasons: (1) the amide carbonyl as an electron-withdrawing group bonded with α-carbon enhanced the acidity of α-H, which is unfavorable for the keto form; (2) the cross-conjugation effects make the enol form stable; and (3) the formation of hydrogen bonds as revealed by X-ray crystallographic also can stabilize the enol form (SI). − With confirmed chemical structures of the model AFAs, the reaction between AFA 1 and AFA 4 was monitored by liquid chromatography–mass spectrometry (LC-MS). In Figure a, there are two new peaks present in the chromatogram and the intensity of the new peaks increased with heating time until an equilibrium (SI).…”