Ultrasound Assisted One-Pot Synthesis of Tetrahydropyrimidne Deriva-tives through Biginelli Condensation: A Catalyst Free Green Chemistry Approach

2020 ◽  
Vol 17 ◽  
Author(s):  
Ashish Patel ◽  
Jinagna Shah ◽  
Kesha Patel ◽  
Krishna Patel ◽  
Harit Patel ◽  
...  
Keyword(s):  
Aromatic Aldehydes ◽  
Green Technology ◽  
Sustainable Chemistry ◽  
Structural Variants ◽  
One Pot ◽  
The Past ◽  
Catalyst Free ◽  
Classical Methodology ◽  
Ultrasound Assisted ◽  
Biginelli Condensation

: The chemical applications of ultrasound, "sonochemistry", has become an exciting new field of research during the past decade as it can increase reactivities by nearly a million fold. Owing to the increasing use of Green technology approach, due to its various merits over Classical methodology and as a need for sustainable Chemistry, this reaction has received renewed interest for preparing tetrahydropyrimidine (THPM) through Biginelii condensation in an environmentally thoughtful manner with improved yields. The classical reaction has been modified in the recent past with/without various catalysts and several structural variants in different solvents to synthesize a large number of Biginelli type compounds due to its diverse pharmacological properties. We reported ultrasound assisted one-pot catalyst free procedure for the synthesis of 6-Aryl substituted-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-Carbonitrile from various aromatic aldehydes, ethyl cyano-acetate and urea under a basic condition with affording isolated yield up to 99% within a reaction time of 5-20 min under mild condition. The synthesized products were characterized by MP, IR, NMR and Mass spectroscopies.

scholarly journals Ag2O/GO/TiO2 Composite Nanostructure: an efficient heterogeneous catalyst for one pot synthesis of Bis (dihydropyrimidinone) and tetrahydro-4H-chromenes derivatives

2021 ◽  
Author(s):  
Fatemeh Samandi Zadeh ◽  
Mohammad Kazem Mohammadi ◽  
Ayeh Raeiatzadeh ◽  
Neda Hasanzadeh
Keyword(s):  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
Synthesis Methods ◽  
X Ray Diffraction ◽  
One Pot ◽  
Transmission Electron ◽  
One Pot Condensation ◽  
Effective Synthesis ◽  
Ft Ir ◽  
Biginelli Condensation

Abstract The simple and efficient synthesis reaction was used for preparing Bis (dihydropyrimidinone) derivatives through Biginelli condensation reaction of terephthalic aldehyde, 1, 3-dicarbonyl compounds and (thio) urea or guanidine and tetrahydro-4H-chromenes via one pot condensation of aromatic aldehydes, malononitrile and dimedone with Ag2O/GO/TiO2 composite nanostructures as a catalyst. The structural functionalities and morphological observations of catalyst were obtained using characterization techniques of field emission scanning electron microscopy (FESEM), X-ray diffraction (XRD), Fourier transfer infrared (FT-IR) spectroscopy and transmission electron microscope (TEM). The structures of Bis (dihydropyrimidinone) and tetrahydro-4H-chromenes confirmed by FT- IR, NMR and mass spectroscopy. Excellent yields of the products, simple reaction process and simple work-up are attractive features of these effective synthesis methods.

One-Pot Solvent-and Catalyst-Free Synthesis of Some New Heteroarylaminonaphthoquinones from Lawsone

2021 ◽  
Vol 18 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Nilufar Rahmani ◽  
Mahdieh Sadeghpour ◽  
Amir Mohamadi
Keyword(s):  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Heterocyclic Amines ◽  
Environmentally Benign ◽  
One Pot ◽  
Simple Operation ◽  
Catalyst Free ◽  
Three Component Reaction ◽  
Methyl Naphthalene ◽  
Work Up

: A clean and efficient one-pot protocol for the synthesis of a series of new 2-hydroxy-3-((3-aryl)(heteroarylamino)methyl)naphthalene-1,4-dione derivatives has been developed by the three-component reaction of 2-hydroxynaphthalene-1,4-dione, aromatic aldehydes and heterocyclic amines at 90 oC under solvent and catalyst-free conditions. The procedure avoids the use of toxic solvents, tedious work-up, catalyst and purification of the products by chromatographic methods. Simple operation, short reaction times, generating the desired compounds in high to excellent yields and an environmentally benign method are advantages of this protocol.

scholarly journals Ag2O/GO/TiO2 Composite Nanostructure: An Efficient Heterogeneous Catalyst for one Pot Synthesis of Bis (Dihydropyrimidinone) and Tetrahydro-4H-chromenes Derivatives

2020 ◽  
Author(s):  
Fatemeh Samandi Zadeh ◽  
Mohammad Kazem Mohammadi ◽  
Ayeh Rayatzadeh ◽  
Neda Hasanzadeh
Keyword(s):  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
Synthesis Methods ◽  
X Ray Diffraction ◽  
One Pot ◽  
Transmission Electron ◽  
One Pot Condensation ◽  
Effective Synthesis ◽  
Ft Ir ◽  
Biginelli Condensation

Abstract The simple and efficient synthesis reaction was used for preparing Bis (dihydropyrimidinone) derivatives through Biginelli condensation reaction of terephthalic aldehyde, 1, 3-dicarbonyl compounds and (thio) urea or guanidine and tetrahydro-4H-chromenes via one pot condensation of aromatic aldehydes, malononitrile and dimedone with Ag2O/GO/TiO2 composite nanostructures as a catalyst. The structural functionalities and morphological observations of catalyst were obtained using characterization techniques of field emission scanning electron microscopy (FESEM), X-ray diffraction (XRD), Fourier transfer infrared (FT-IR) spectroscopy and transmission electron microscope (TEM). The structures of Bis (dihydropyrimidinone) and tetrahydro-4H-chromenes confirmed by FT- IR, NMR and mass spectroscopy. Excellent yields of the products, simple reaction process and simple work-up are attractive features of these effective synthesis methods.

Fast and Efficient One-Pot Three-Component Synthesis of Some 1,2,3,4- Tetrahydro-6-methyl-N-phenyl-5-pyrimidinecarboxamide Derivatives via Biginelli Condensation Reaction

2020 ◽  
Vol 17 (5) ◽  
pp. 366-371 ◽  
Author(s):  
Şirin Gülten ◽  
Ufuk Gezer ◽  
Elmas Aksanli Gündoğan
Keyword(s):  
Medicinal Chemistry ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
Heterocyclic Ring ◽  
Biological Properties ◽  
Spectroscopic Techniques ◽  
One Pot ◽  
Efficient Catalyst ◽  
Biginelli Condensation

Tetrahydropyrimidine (THPM) synthesis has an enormous importance in organic chemistry and especially in pharmaceutical applications. Pyrimidines are the most active class of N-containing heterocyclic compounds and have different biological properties. The heterocyclic ring system with a thio group occupy a unique position in medicinal chemistry. This type of compounds play an important role in synthetic drugs and in biological processes. Dihydropyrimidinethione derivatives occur widely in nature. Several modifications of THPM-5-carboxamides have attracted considerable interest of medicinal chemists due to their pharmacological and therapeutic properties. A series of 1,2,3,4-tetrahydro- 2-pyrimidinone/thione derivatives bearing a phenylcarbamoyl group at C-5 position were synthesized by one-pot three-component Biginelli condensation reaction. The reaction of acetoacetanilide as the 1,3-dicarbonyl component with various aromatic aldehydes and urea/thiourea in the presence of a catalytic amount of p-toluenesulfonic acid monohydrate (PTSA·H2O) or concentrated HCl as an efficient catalyst leads to Biginelli compounds. We have prepared eight THPM 5-carboxamide derivatives, four of them are new compounds. Their structures were confirmed by spectroscopic techniques and elemental analysis. These compounds have potential applications in organic synthesis and medicinal chemistry. We have synthesized a series of THPM-5-carboxamides by simple and efficient threecomponent Biginelli condensation reaction. Significant benefits of the present procedure include: a) application of inexpensive, non-toxic, environmentally friendly and easily available catalysts, b) the reactions are easy to carry out without high temperature and the workup is very simple, c) the required reaction times are relatively short (30-80 min with HCl and 8-24 h with PTSA·H2O), d) compatibility with various functional groups, e) the products are isolated in good to excellent yields (50-95%).

Microwave-assisted One-pot Synthesis of 7-Dimethylamino-4-Aryl-2- methylamino-3-nitro-4H-chromenes

2019 ◽  
Vol 16 (6) ◽  
pp. 468-473
Author(s):  
Pallava Nagaraju ◽  
Pannala Padmaja ◽  
Pedavenkatagari Narayana Reddy
Keyword(s):  
Aromatic Aldehydes ◽  
Synthetic Methods ◽  
Quinone Methide ◽  
Chromatographic Purification ◽  
One Pot ◽  
Dimethylamino Group ◽  
Microwave Assisted ◽  
Catalyst Free ◽  
One Pot Condensation ◽  
Direct Use

4-Aryl-2-amino-4H-chromenes possessing N,N-dimethylamino group have been reported as potential anticancer drugs. Despite few synthetic methods reported in the literature for their synthesis, there appear to be no reports on the direct use of N,N-dimethyl-3-aminophenol for the synthesis of 4- aryl-2-methylamino-3-nitro-4H-chromenes. One-pot condensation of N,N-dimethyl-3-aminophenol, aromatic aldehydes and (E)-N-methyl-1-(methylthio)-2-nitro-ethenamine was carried out using MW irradiation to get the 4-aryl-2-methylamino-3-nitro-4H-chromenes under catalyst-free conditions. This transformation presumably occurs via o-quinone methide formation, Michael addition-intramolecular O-cyclization-elimination sequence of reactions creating new two C-C bonds and one C-O bond. Various substituted aromatic aldehydes reacted smoothly with N,N-dimethyl-3-aminophenol and (E)-Nmethyl- 1-(methylthio)-2-nitro-ethenamine to give the corresponding 4-aryl-2-methylamino-3-nitro-4Hchromenes in good yields. We have developed a one-pot three component condensation of N,Ndimethyl- 3-aminophenol, aromatic aldehyde and NMSM for the synthesis of N,N-dimethylamino substituted 4-aryl-2-methylamino-3-nitro-4H-chromenes in good yields. The significant features of this reaction include catalyst-free, solvent free, no column chromatographic purification, short reaction time and good yields.

Enviro-economic, Ultrasound-assisted One-pot, Three-component Synthesis of Pyrido[2,3-d]pyrimidines in Aqueous Medium

2012 ◽  
Vol 67 (3) ◽  
pp. 231-237 ◽  
Author(s):  
Essam M. Hussein
Keyword(s):  
Reaction Time ◽  
Phase Transfer ◽  
Ethyl Cyanoacetate ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Ammonium Bromide ◽  
One Pot ◽  
Short Reaction Time ◽  
Ultrasound Assisted ◽  
Work Up

Tetra-n-butyl ammonium bromide (TBAB) was found to be an efficient phase-transfer catalyst for the synthesis of pyrido[2,3-d]pyrimidines by one-pot reaction of 6-aminouracils, aromatic aldehydes, and malononitrile or ethyl cyanoacetate in water under ultrasonic irradiation. The advantages of this method are the use of an inexpensive and readily available catalyst, short reaction time, easy work-up, improved yields, and the use of water as a solvent that is environmentally benign.

An efficient and catalyst-free synthesis of N-arylidene-2-arylimidazo[1,2-a]pyridine-3-ylamine derivatives via Strecker reaction under controlled microwave heating

2017 ◽  
Vol 6 (4) ◽  
Author(s):  
Afaf Mohamed Abdel Hameed ◽  
Moustafa Sherief Moustafa ◽  
Saleh Mohammed Al-Mousawi ◽  
Reham R. Awed ◽  
Kamal Usef Sadek
Keyword(s):  
Microwave Heating ◽  
Multicomponent Reaction ◽  
Aromatic Aldehydes ◽  
Atom Economy ◽  
One Pot ◽  
Strecker Reaction ◽  
Catalyst Free ◽  
Benzoyl Cyanide

AbstractAn efficient one-pot multicomponent reaction of 2-aminopyridine with aromatic aldehydes and either benzoyl cyanide or cyanamide in pyridine under controlled microwave heating afforded N-aryldene-2-arylimidazo[1,2-a]-pyridine-3-ylamine derivatives. The reaction is catalyst free and is of high atom economy.

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex

2020 ◽  
Author(s):  
José Tiago Menezes Correia ◽  
Gustavo Piva da Silva ◽  
Camila Menezes Kisukuri ◽  
Elias André ◽  
Bruno Pires ◽  
...  
Keyword(s):  
Electron Donor ◽  
Functional Group ◽  
Photoexcited Electron ◽  
One Pot ◽  
Quaternary Centers ◽  
Metal Free ◽  
Acceptor Complex ◽  
Catalyst Free ◽  
Donor Acceptor ◽  
Radical Cascade

A metal- and catalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a SET event involving a photoexcited electron-donor-aceptor complex between NHPI ester and Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. <a>The method provides an operationally simple, robust and step-economical approach to the construction of diversely functionalized dihydroquinolinones bearing quaternary-centers. A sequential one-pot hydroalkylation-isomerization approach is also allowed giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance was observed in both approaches</a>.

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