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.

scholarly journals A multicomponent, facile and catalyst-free microwave-assisted protocol for the synthesis of pyrazolo-[3,4-b]-quinolines under green conditions

RSC Advances ◽  
2019 ◽  
Vol 9 (53) ◽  
pp. 30768-30772 ◽  
Author(s):  
Mandlenkosi Robert Khumalo ◽  
Surya Narayana Maddila ◽  
Suresh Maddila ◽  
Sreekantha B. Jonnalagadda
Keyword(s):  
Ambient Temperature ◽  
Aqueous Ethanol ◽  
Reaction Medium ◽  
One Pot ◽  
Microwave Assisted ◽  
Catalyst Free ◽  
Green Conditions

A facile, swift and ecofriendly microwave-assisted multi-component/one-pot protocol is designed for the synthesis of novel pyrazolo-[3,4-b]-quinolines at ambient temperature in aqueous ethanol as a reaction medium.

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.

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.

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 In situ synthesis of SO3H supported Fe3O4@resorcinol–formaldehyde resin core/shell and its catalytic evaluation towards the synthesis of hexahydroquinoline derivatives in green conditions

RSC Advances ◽  
2020 ◽  
Vol 10 (68) ◽  
pp. 41703-41712
Author(s):  
Aliyeh Barzkar ◽  
Alireza Salimi Beni
Keyword(s):  
Ammonium Acetate ◽  
Aromatic Aldehydes ◽  
In Situ Synthesis ◽  
Formaldehyde Resin ◽  
One Pot ◽  
Resorcinol Formaldehyde ◽  
Resin Core ◽  
One Pot Condensation ◽  
Green Conditions

A novel core@double-shell acidic nanocatalyst (Fe3O4@SiO2@RF–SO3H) was prepared, characterized and applied in catalytic one-pot condensation between aromatic aldehydes, dimedone, malononitrile, and ammonium acetate for synthesis of hexahydroquinoline derivatives.

Green catalyst-free one-pot synthesis of novel tetrahydropyridine-3-carboxamides by microwave-assisted approach

2020 ◽  
Vol 132 (1) ◽  
Author(s):  
Mandlenkosi Khumalo ◽  
Surya Narayana Maddila ◽  
Suresh Maddila ◽  
Sreekantha B Jonnalagadda
Keyword(s):  
One Pot ◽  
Green Catalyst ◽  
Microwave Assisted ◽  
Catalyst Free ◽  
One Pot Synthesis

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.

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