57270-86-7Relevant academic research and scientific papers
Diversity-oriented Multicomponent Heterocyclizations Involving Derivatives of 3(5)-Aminoisoxazole, Aldehydes and Meldrum's or N,N′-Dimethylbarbituric Acid
Morozova, Alisa D.,Muravyova, Elena A.,Shishkina, Svitlana V.,Vashchenko, Elena V.,Sen'ko, Yulia V.,Chebanov, Valentin A.
, p. 932 - 943 (2017)
5-Amino-3-methylisoxazole and 3-amino-5-methylisoxazole were studied in details in the multicomponent heterocyclizations with aromatic aldehydes and Meldrum's or N,N′-dimethylbarbituric acid with help of classical and non-classical (microwave and ultrasonic irradiation) activation methods.
L-Proline based ionic liquid: A highly efficient and homogenous catalyst for synthesis of 5-benzylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione and pyrano[2,3-d] pyrimidine diones under ultrasonic irradiation
Patil, Paresh G.,Satkar, Yuvraj,More, Dhananjay H.
, p. 3804 - 3819 (2020/09/01)
A catalytic, practical, efficient procedure for the synthesis of 5-benzylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione and pyrano[2,3-d] pyrimidine diones at room temperature was developed using L-Proline nitrate ionic liquid under ultrasonic irradiation. The L-Proline nitrate is homogeneous and green catalyst easy to prepare by mixing L-Proline and nitric acid possess excellent catalytic activity under standard ultrasonic bath at room temperature for the synthesis of pyrimidine core. This adequate procedure offers some advantages like the use of green solvent H2O, environmentally green benign procedure, excellent yields, simple procedure, short reaction times, no need for column chromatographic separation and reusability of catalyst for five subsequent reaction.
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.
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
supporting information, p. 9200 - 9208 (2019/11/05)
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.
Dynamic Covalent Metathesis in the C=C/C=N Exchange between Knoevenagel Compounds and Imines
Gu, Ruirui,Flidrova, Karolina,Lehn, Jean-Marie
supporting information, p. 5560 - 5568 (2018/05/01)
Fast and reversible dynamic covalent C=C/C=N exchange takes place without catalyst in nonpolar solvents between barbiturate-derived Knoevenagel (Kn) compounds and imines. A detailed study of the reaction indicates that it proceeds by an associative organo-metathesis mechanism involving the formation of a four-membered ring azetidine intermediate by addition of the imine C=N group to the C=C bond of the Kn compound. This intermediate could be generated cleanly and stabilized at low temperature by condensation of the o,p-dinitrophenyl Kn derivative with the cyclic imine 1-azacyclohexene. It was characterized by extensive NMR and mass spectrometric studies. The process described represents a genuine dynamic covalent organo-metathesis through a four-membered ring adduct as intermediate. It paves the way for the exploration of a wide set of dynamic systems involving (strongly) polarized C=C bonds and various imines, extending also into covalent dynamic polymers and polymolecular assemblies.
“On-water” catalyst-free, one-pot synthesis of quaternary centered and spiro-tetrahydrothiophene-barbiturate hybrids
Nagaraju, Sakkani,Sathish, Kota,Paplal, Banoth,Kashinath, Dhurke
supporting information, p. 2865 - 2871 (2017/06/27)
A green and efficient method have been developed for the synthesis of quaternary centered and spiro-barbiturate-tetrahydrothiophene hybrids via Knoevenagel condensation,1,4-thia-Michael and intramolecular Aldol reactions using “on water” concept under catalyst-free conditions. Systematic studies were carried out to find the role of the water and total reaction concentration (0.086?M) to promote the reaction in two steps (one-pot). The use of water as a reaction medium, catalyst-free conditions, broad substrate scope, one-pot approach for the creation of quaternary centered and spiro molecules are the advantages of this method.
Efficient one-pot synthesis of some new pyrimido[5′,4′:5,6]pyrido[2,3-d]pyrimidines catalyzed by magnetically recyclable Fe3O4 nanoparticles
Fattahi,Davoodnia,Pordel
, p. 863 - 867 (2017/05/29)
The study is devoted to one-pot reaction of 1,3-dimethylbarbituric acid with aromatic aldehydes and ammonium acetate using Fe3O4 nanoparticles as efficient and magnetically recyclable catalysts. Aromatic aldehydes substituted with electron-withdrawing groups or none, reacted successfully with 1,3-dimethylbarbituric acid and ammonium acetate to give new pyrimido[5′,4′:5,6]pyrido[2,3-d]pyrimidine derivatives (can be also named as pyrido[2,3-d:6,5-d′]dipyrimidines) in high yields over relatively short reaction time. The Knoevenagel condensation products were isolated using aromatic aldehydes bearing electron-donating substituents. The catalyst could be efficiently used for four times without substantial reduction in its activity. The new products were characterized on the basis of FT-IR, 1H NMR and 13C NMR spectral data.
Asymmetric Construction of Highly Functionalized Spirobarbiturate-Cyclopentenes through Chiral Phosphine-Catalyzed [3+2] Annulation of Morita–Baylis–Hillman Carbonates with Barbiturate-Derived Alkenes
Liu, Yang,Yang, Wenjun,Wu, Yang,Mao, Biming,Gao, Xing,Liu, Honglei,Sun, Zhanhu,Xiao, Yumei,Guo, Hongchao
supporting information, p. 2867 - 2872 (2016/09/16)
A multifunctional chiral phosphine-catalyzed enantioselective [3+2] annulation of Morita–Baylis–Hillman carbonates with barbiturate-derived alkenes has been achieved under mild conditions, providing a variety of chiral spirobarbiturate-cyclopentenes in moderate to excellent yields with moderate to excellent diastereo- and enantioselectivities. (Figure presented.).
Effect of reaction parameters on the synthesis of 5-arylidene barbituric acid derivatives in ball mills
Schmidt, Robert,Burmeister, Christine F.,Balá?, Matej,Kwade, Arno,Stolle, Achim
supporting information, p. 427 - 436 (2015/04/14)
The influence of crucial reaction parameters on Knoevenagel condensation in planetary ball mills was investigated. Rotation frequency (νrot), milling ball diameter (dMB), milling ball filling degree (φMB), and beaker size
Synthesis of Phenanthrene Derivatives through the Reaction of an α,α-Dicyanoolefin with α,β-Unsaturated Carbonyl Compounds
Alizadeh, Abdolali,Hosseini, Seyed Yasub,Sedighian, Hadi,Bayat, Fahimeh
, p. 1426 - 1434 (2015/10/20)
Phenanthrene derivatives were prepared by reacting an α,α-dicyanoolefin with different α,β-unsaturated carbonyl compounds resulting from Wittig reaction of ninhydrin and phosphanylidene or condensation of barbituric acid and an aldehyde. The easy procedure, mild and metal-catalyst free, reaction conditions, good yields, and no need for chromatographic purifications are important features of this protocol. The structures of the product of type 3 and 5 were corroborated spectroscopically (IR, 1H- and 13C-NMR, and EI-MS). A plausible mechanism for this type of reaction is proposed (Scheme 1).
