Catalyst-free aza-Michael addition for C–N coupling in active pharmaceutical ingredient synthesis: Modelling of thermodynamic, reaction kinetics and mass transfer considerations

2019 ◽  
Vol 374 ◽  
pp. 924-936
Author(s):  
Marko Trampuž ◽  
Gaj Stavber ◽  
Blaž Likozar
Keyword(s):  
Mass Transfer ◽  
Reaction Kinetics ◽  
Michael Addition ◽  
Active Pharmaceutical Ingredient ◽  
Catalyst Free

Catalyst-Free One-Pot Synthesis of Novel Heteroarylamine Substituted Furo[3,2-c]coumarins

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1589-1592 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Mahnaz Saraei ◽  
Reyhaneh Khoeiniha
Keyword(s):  
Michael Addition ◽  
Aldol Condensation ◽  
Ring Closure ◽  
Dehydration Reaction ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Tandem Process ◽  
First Time

A high-yielding cyclocondensation of 4-hydroxycoumarin, phenylglyoxal monohydrate, and heteroarylamines proceeds without catalysis, which gives novel functionalized furo[3,2-c]coumarins and heteroarylamino alkylation of coumarin products in acetonitrile under reflux, is reported for the first time. This tandem process involves sequentially an aldol condensation, Michael addition, a ring closure, and dehydration reaction.

Base and catalyst-free synthesis of nitrobenzodiazepines via a cascade N-nitroallylation-intramolecular aza-Michael addition involving o-phenylenediamines and nitroallylic acetates

Tetrahedron ◽  
2019 ◽  
Vol 75 (51) ◽  
pp. 130761 ◽  
Author(s):  
Divya K. Nair ◽  
Sudheesh T. Sivanandan ◽  
Pravin Kendrekar ◽  
Irishi N.N. Namboothiri
Keyword(s):  
Michael Addition ◽  
Catalyst Free

CFD Simulation of the Particle Dispersion Behavior and Mass Transfer–Reaction Kinetics in non-Newton Fluid with High Viscosity

2019 ◽  
Vol 17 (7) ◽  
Author(s):  
Le Xie ◽  
Qi-An Wang ◽  
Xian-Jin Luo ◽  
Zheng-Hong Luo
Keyword(s):  
Mass Transfer ◽  
Reaction Kinetics ◽  
Transfer Reaction ◽  
High Viscosity ◽  
Particle Dispersion ◽  
Agitation Speed ◽  
Fluid Viscosity ◽  
Condensation Polymerization ◽  
Cross Model ◽  
Dispersion Behavior

Abstract Solid particle dispersion and chemical reactions in high-viscosity non-Newtonian fluid are commonly encountered in polymerization systems. In this study, an interphase mass transfer model and a finite-rate/eddy-dissipation formulation were integrated into a computational fluid dynamics model to simulate the dispersion behavior of particles and the mass transfer–reaction kinetics in a condensation polymerization-stirred tank reactor. Turbulence fields were obtained using the standard k–ε model and employed to calculate the mixing rate. Cross model was used to characterize the rheological property of the non-Newton fluid. The proposed model was first validated by experimental data in terms of input power. Then, several key operating variables (i.e. agitation speed, viscosity, and particle size) were investigated to evaluate the dispersive mixing performance of the stirred vessel. Simulation showed that a high agitation speed and a low fluid viscosity favored particle dispersions. This study provided useful guidelines for industrial-scale high-viscosity polymerization reactors.

Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [e]-Fused 1H-Pyrrole-2,3-diones

Synthesis ◽  
2018 ◽  
Vol 50 (24) ◽  
pp. 4897-4904 ◽  
Author(s):  
Ekaterina Stepanova ◽  
Andrey Maslivets ◽  
Svetlana Kasatkina ◽  
Maksim Dmitriev
Keyword(s):  
Intramolecular Cyclization ◽  
Aromatic Hydrocarbons ◽  
Michael Addition ◽  
Aldol Reaction ◽  
Synthetic Approach ◽  
Reaction Conditions ◽  
Diversity Oriented Synthesis ◽  
Catalyst Free ◽  
Solvent Free Conditions ◽  
Reaction Proceeds

A facile synthetic approach towards two distinct pyrrole-based heterocyclic scaffolds has been developed by the interaction of 1H-pyrrole-2,3-diones fused at the [e]-side to a 1,4-benzoxazin-2-one or quinoxalin-2(1H)-one moiety with ketones. The described interaction proceeds either as an aldol reaction or as a Michael addition/intramolecular cyclization depending on the reaction conditions. The disclosed aldol reaction proceeds with good diastereoselectivity under catalyst-free conditions when the reaction is carried out in aromatic hydrocarbons. Products of the cascade Michael addition/intramolecular cyclization reaction are predominantly formed under catalyst-free and solvent-free conditions. The proposed strategy provides facile access to pharmaceutically interesting pyrrole-based polyheterocycles.

A study on mass transfer–reaction kinetics of NO absorption by using UV/H2O2/NaOH process

Fuel ◽  
2013 ◽  
Vol 108 ◽  
pp. 254-260 ◽  
Author(s):  
Yangxian Liu ◽  
Jianfeng Pan ◽  
Aikun Tang ◽  
Qian Wang
Keyword(s):  
Mass Transfer ◽  
Reaction Kinetics ◽  
Transfer Reaction ◽  
Kinetics Of ◽  
No Absorption

scholarly journals Substrate-controlled Diastereoselective Michael Addition of Alkylidene Malonates by Grignard Reagents

2019 ◽  
Vol 25 (1) ◽  
pp. 116-121
Author(s):  
Wei Zhou ◽  
Qingwei Xiao ◽  
Yuanyuan Chang ◽  
Qifa Liu ◽  
Xiaohao Zang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Chiral Auxiliary ◽  
Grignard Reagents ◽  
Amino Acid Derivatives ◽  
Catalyst Free ◽  
Chemical Efficiency

AbstractHerein is described a diastereoselective Michael addition of Grignard reagents to α, β- unsaturated diethyl malonates incorporated with a 2-oxazolidone chiral auxiliary. The catalyst-free Michael addition proceeds with good chemical efficiency and excellent stereoselectivity; and it provides new thoughts to the asymmetric synthesis of β-substituted β3 amino acid derivatives.

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