114702-44-2Relevant academic research and scientific papers
Synthesis of spirobarbiturate-pyrrolidinones: Via a domino aza-Michael/SN2 cyclization of barbiturate-derived alkenes with N-alkoxy α-haloamides
Wang, Chuan-Chuan,Zhou, Jing,Ma, Zhi-Wei,Chen, Xiao-Pei,Chen, Ya-Jing
, p. 9200 - 9208 (2019)
A highly efficient domino aza-MIRC (Michael Induced Ring Closure) reaction between barbiturate-derived alkenes and N-alkoxy α-haloamides has been achieved in moderate to excellent yields. This reaction proceeds smoothly under mild conditions via a domino aza-Michael addition/intramolecular SN2 sequence, providing a practical tool in the synthesis of bioactive molecules spirobarbiturate-3-pyrrolidinones.
One-Pot Knoevenagel and [4 + 2] Cycloaddition as a Platform for Calliviminones
Roy, Pritam,Anjum, S. Rehana,Ramachary, Dhevalapally B.
supporting information, p. 2897 - 2901 (2020/04/15)
Bioactive compounds featuring an unusual core of spiro[5.5]undecenes and calliviminones were synthesized in very good yield with good regio- and diastereoselectivities through a one-pot Knoevenagel and [4 + 2] cycloaddition from the readily available aldehydes, cyclic-1,3-diones, dienes, and a catalytic amount of (s)-proline.
Determination of thermodynamic affinities of various polar olefins as hydride, hydrogen atom, and electron acceptors in acetonitrile
Cao, Ying,Zhang, Song-Chen,Zhang, Min,Shen, Guang-Bin,Zhu, Xiao-Qing
, p. 7154 - 7168 (2013/08/23)
A series of 69 polar olefins with various typical structures (X) were synthesized and the thermodynamic affinities (defined in terms of the molar enthalpy changes or the standard redox potentials in this work) of the polar olefins obtaining hydride anions, hydrogen atoms, and electrons, the thermodynamic affinities of the radical anions of the polar olefins (X ?-) obtaining protons and hydrogen atoms, and the thermodynamic affinities of the hydrogen adducts of the polar olefins (XH?) obtaining electrons in acetonitrile were determined using titration calorimetry and electrochemical methods. The pure Ci - 'C π-bond heterolytic and homolytic dissociation energies of the polar olefins (X) in acetonitrile and the pure Ci - 'C π-bond homolytic dissociation energies of the radical anions of the polar olefins (X?-) in acetonitrile were estimated. The remote substituent effects on the six thermodynamic affinities of the polar olefins and their related reaction intermediates were examined using the Hammett linear free-energy relationships; the results show that the Hammett linear free-energy relationships all hold in the six chemical and electrochemical processes. The information disclosed in this work could not only supply a gap of the chemical thermodynamics of olefins as one class of very important organic unsaturated compounds but also strongly promote the fast development of the chemistry and applications of olefins.
5-Arylidene 1,3-Dimethylbarbituric Acid Derivatives, Mild Organic Oxidants for Allylic and Benzylic Alcohols
Tanaka, Kiyoshi,Chen, Xing,Kimura, Teiji,Yoneda, Fumio
, p. 60 - 69 (2007/10/02)
Various 5-arylidene 1,3-dimethylbarbituric acid derivatives and closely related compounds were synthesized as models of redox coenzymes and used for oxidation of alcohols.Under mild neutral conditions, 5-arylidene 1,3-dimethylbarbituric acid derivatives, especially those having an electron-withdrawing group on the aromatic ring, effectively oxidized allylic and benzylic alcohols to the corresponding carbonyl compounds.The relationship between the oxidizing ability and the structure of the oxidant (coenzyme model) was investigated and it was found that the electron density on the carbon-carbon double bond is a critical factor for the oxidation.In the case of the deuterium-labeled compound, the observed value of normal and primary isotope effect was 3.3 and so it was concluded that mechanism of this oxidation mainly involves the hydride transfer from the alcohol.An electrochemical investigation was also carried out and the redox potentials of the coenzyme models, 5-arylidene 1,3-dimethylbarbituric acid derivatives and related compounds, were measured.Keywords - 5-arylidene 1,3-dimethylbarbituric acid; coenzyme model; oxidation; allylic alcohol; benzylic alcohol; oxidation mechanism; hydride transfer; primary isotope effect; cyclic voltammetry; redox potential
