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%).

scholarly journals Acid Catalyzed Multicomponent One-Pot Synthesis of New Quinazolinone based Unsymmetrical C-N Linked Bis Heterocycles

2022 ◽  
Vol 34 (2) ◽  
pp. 432-436
Author(s):  
Nagamani Rayala ◽  
Sumathi Vodnala ◽  
Supriya Kamsani ◽  
A.K.D. Bhavani ◽  
Nagaraju Myakala ◽  
...  
Keyword(s):  
Hydrochloric Acid ◽  
13C Nmr ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
Heterocyclic Ring ◽  
Spectroscopic Techniques ◽  
One Pot ◽  
Hybrid Compounds ◽  
Three Component Reaction ◽  
Acid Catalyzed

A novel series of unsymmetrical C-N linked bis heterocycles bearing quinazolinone and acridinedione skeletons have been synthesized in an acid promoted one pot multicomponent reaction. A blend of 6-aminoquinazolin-4-(3H)-one, aromatic aldehydes and cyclohexane-1,3-dione in a simple and efficient condensation-cyclization reaction using hydrochloric acid in catalytic amount as catalyst afforded unsymmetrical bis hybrids in good to excellent yields. Multiheterocyclic hybrid compounds were also synthesized using heterocyclic ring containing aldehyde in three component reaction. The synthesized quinazolinone-acridindione hybrids were characterized using spectroscopic techniques such as a IR, 1H NMR, 13C NMR, ESI-mass and HRMS.

TiO2 Nanoparticles as an Efficient Catalyst for the One-pot Preparation of Tetrahydrobenzo[c]acridines in Aqueous Media

2013 ◽  
Vol 68 (4) ◽  
pp. 362-366 ◽  
Author(s):  
Shahrzad Abdolmohammadi ◽  
Mahdieh Mohammadnejad ◽  
Faezeh Shafaei
Keyword(s):  
Ammonium Acetate ◽  
Titanium Dioxide Nanoparticles ◽  
Aqueous Media ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
One Pot ◽  
Efficient Catalyst ◽  
The One ◽  
Work Up ◽  
Operational Simplicity

A series of tetrahydrobenzo[c]acridinone derivatives have been prepared by a one-pot fourcomponent reaction of 1-naphthol, aromatic aldehydes, dimedone, and ammonium acetate in aqueous media using a catalytic amount of titanium dioxide nanoparticles (TiO2 NPs). The advantages of this novel protocol include the excellent yields, operational simplicity, short reaction time, easy work-up, reusability of the catalyst and an environmentally friendly procedure.

scholarly journals Leucine: green and efficient catalyst for the synthesis of 4H-chromenes

2017 ◽  
Vol 10 (9) ◽  
pp. 3197-3202 ◽  
Author(s):  
Davood Azarifar ◽  
Younes Abbasi ◽  
Omolbanin Badalkhani
Keyword(s):  
Amino Acid ◽  
Condensation Reaction ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
One Pot ◽  
Efficient Catalyst ◽  
Naturally Occurring ◽  
The One ◽  
High Yields ◽  
Work Up

Leucine, a naturally occurring α-amino acid, has been found as an effective catalyst to effect the one-pot three-component condensation reaction between aromatic aldehydes, malononitrile and 5,5-dimethyl-1,3-cyclohexanedione (dimedone). Various 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile derivatives are conveniently prepared by these reactions in excellent yields. High yields, short reaction times, simple work-up, use of green and naturally occurring catalyst and solvent are the main merits of the present protocol. 

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.

scholarly journals Solvent-free preparation of amidoalkyl phenols catalyzed by trityl chloride under neutral media

2015 ◽  
Vol 93 (11) ◽  
pp. 1245-1248 ◽  
Author(s):  
Ahmad Reza Moosavi-Zare ◽  
Mohammad Ali Zolfigol ◽  
Fateme Derakhshan-Panah ◽  
Masoume Daraei
Keyword(s):  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
Solvent Free ◽  
One Pot ◽  
Multicomponent Condensation ◽  
Solvent Free Condition ◽  
Neutral Media ◽  
In Situ Generation

A one-pot, multicomponent condensation reaction of phenols, aromatic aldehydes, and amides in the presence of catalytic amount of trityl chloride as a homogeneous organocatalyst under solvent-free condition to prepare amidoalkyl phenols has been reported. It is interesting that trityl chloride by in situ generation of trityl carbocation with inherent instability catalyzes the reaction.

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.

scholarly journals Trichloroisocyanuric acid, a New and Efficient Catalyst for the Synthesis of 2′- Aminobenzothiazolo-arylmethyl-2-naphthols

2012 ◽  
Vol 9 (4) ◽  
pp. 2424-2428 ◽  
Author(s):  
Limin Yang
Keyword(s):  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
Solvent Free ◽  
One Pot ◽  
Efficient Catalyst ◽  
One Pot Synthesis ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
Trichloroisocyanuric Acid

An efficient one-pot synthesis of 2′-aminobenzothiazolo-arylmethyl-2-naphthols is described. This involves the three-component reaction ofβ-naphthol, aromatic aldehydes and 2-aminobenzothiazole in the presence of a catalytic amount of trichloroisocyanuric acid under solvent-free conditions.

scholarly journals Bi-SO3H Functionalized Ionic Liquid Based on DABCO: New and Efficient Catalyst for Facile Synthesis of Dihydropyrimidinones

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Firouzeh Nemati ◽  
Sara G. Alizadeh
Keyword(s):  
Ionic Liquid ◽  
Efficient Method ◽  
Condensation Reaction ◽  
Facile Synthesis ◽  
One Pot ◽  
Efficient Catalyst ◽  
Dicarbonyl Compounds ◽  
Functionalized Ionic Liquid ◽  
The One ◽  
Biginelli Condensation

A simple and efficient method for the one-pot Biginelli condensation reaction of aldehydes,β-dicarbonyl compounds, and urea or thiourea employing [DABCO](SO3H)2Cl2as a novel ionic liquid catalyst is described.

scholarly journals Tandem reaction for the synthesis of bicyclic ortho-aminocarbonitrile derivatives using DMAPA as a cheap and efficient catalyst

2020 ◽  
Vol 2 (2) ◽  
pp. 145-151
Author(s):  
Lisha Wu ◽  
◽  
Shiqiang Yan ◽  
Yinta Li ◽  
◽  
...  
Keyword(s):  
Aromatic Aldehyde ◽  
Multicomponent Reaction ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
New Method ◽  
Tandem Reaction ◽  
One Pot ◽  
Efficient Catalyst ◽  
Simple Filtration

To develop a new method for the synthesis of bicyclic ortho-aminocarbonitrile derivatives. Reaction of aromatic aldehydes, cycloketones and malononitrile with catalytic amount of 3-(dimethylamino)- 1-propylamine (DMAPA) in ethanol via Knoevenagel-Michael cascades. The bicyclic ortho-aminocarbonitrile derivatives were obtained with good to excellent yields along with short reaction times. The universality, excellent yields, mild reaction and easy collection through simple filtration indicate the preparation of orthoaminocarbonitriles derivatives is an efficient and suitable protocol, which use one-pot multicomponent reaction of aromatic aldehyde, cycloketone, and 2 equiv. of malononitrile under the catalytic amount of DMAPA in ethanol.

Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde

2018 ◽  
Vol 21 (4) ◽  
pp. 298-301 ◽  
Author(s):  
Ghasem Marandi
Keyword(s):  
Biological Sciences ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
High Performance ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
New Materials ◽  
One Pot ◽  
High Yields ◽  
Benzaldehyde Derivatives

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

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