Selective synthesis of tetrahydroimidazo[1,2-a]pyridine and pyrrolidine derivatives via a one-pot two-step reaction

2017 ◽  
Vol 15 (38) ◽  
pp. 8072-8077 ◽  
Author(s):  
Yu Zhang ◽  
Jing Sun ◽  
Guo-Liang Shen ◽  
Chao-Guo Yan
Keyword(s):  
Amino Acid ◽  
Addition Reaction ◽  
Aromatic Aldehydes ◽  
Selective Synthesis ◽  
Pyridine Derivatives ◽  
Alkyl Esters ◽  
One Pot

In the presence of triethylamine, the addition reaction of substituted α-amino acid alkyl esters with dialkyl but-2-ynedioate afforded active β-enamino esters, which in turn reacted with aromatic aldehydes and malononitrile to give tetrahydroimidazo[1,2-a]pyridine derivatives in moderate yields.

scholarly journals Tandem four-component reaction for efficient synthesis of dihydrothiophene with substituted amino acid ethyl esters

RSC Advances ◽  
2018 ◽  
Vol 8 (40) ◽  
pp. 22498-22505 ◽  
Author(s):  
Jing Sun ◽  
Yu Zhang ◽  
Chao-Guo Yan
Keyword(s):  
Amino Acid ◽  
Aromatic Aldehydes ◽  
Ethyl Esters ◽  
Efficient Synthesis ◽  
One Pot ◽  
The One

The one-pot four-component reaction of aromatic aldehydes, malononitrile, 1,3-thiazolidinedione and ethyl glycinate hydrochloride in ethanol in the presence of triethylamine afforded trans-dihydrothiophene.

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. 

′′One-Pot′′ Selective Synthesis of 3,4-Disubstituted Pyrroles and Benzo[f]indole-4,9-diones from 1,3-Indanedione, Aromatic Aldehydes and TosMIC

2017 ◽  
Vol 2 (24) ◽  
pp. 7246-7250 ◽  
Author(s):  
Anjaiah Aitha ◽  
Nagaraju Payili ◽  
Santhosh Reddy Rekula ◽  
Satyanarayana Yennam ◽  
Jaya Shree Anireddy
Keyword(s):  
Aromatic Aldehydes ◽  
Selective Synthesis ◽  
One Pot

scholarly journals One-pot, three-component, selective synthesis of the polyfunctionalized 4H-pyran and 4H-benzo[b]pyran derivatives in the presence of a highly efficient molecular sieve-supported zinc catalyst

2018 ◽  
Vol 7 (4) ◽  
pp. 316-322 ◽  
Author(s):  
Ágnes Magyar ◽  
Zoltán Hell
Keyword(s):  
Reaction Time ◽  
Ethyl Acetoacetate ◽  
Molecular Sieve ◽  
Aromatic Aldehydes ◽  
Selective Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Dicarbonyl Compound ◽  
Short Reaction Time ◽  
One Pot Condensation

Abstract A series of pentasubstituted 4H-pyrans and tetrahydrobenzo[b]pyrans are synthesized with excellent yields via a one-pot condensation of aromatic aldehydes, malononitrile, and a dicarbonyl compound, ethyl acetoacetate, acetyl-acetone or dimedone, in the presence of 4 Å molecular sieve modified with zinc(II) as heterogeneous catalyst, in ethanol. The process offers numerous advantages, such as better yield, short reaction time, and mild reaction conditions. The catalyst’s preparation is simple and it could be reused while still maintaining its activity.

Convenient Synthesis of 2,4-Disubstituted Chromeno[4,3-b]Pyridine by Microwave Assisted One Pot Three Component Protocol

2020 ◽  
Vol 17 ◽  
Author(s):  
Ghanshyam Jadhav ◽  
Vijay Medhane ◽  
Dattatray Deshmukh
Keyword(s):  
Reaction Time ◽  
Microwave Irradiation ◽  
Aromatic Aldehydes ◽  
Pyridine Derivatives ◽  
Substituted Anilines ◽  
One Pot ◽  
Microwave Assisted ◽  
Synthetic Strategy ◽  
Convenient Synthesis ◽  
Scalable Synthesis

: We herein, describe efficient and scalable synthesis of 2,4-diaryl substituted chromene [43-b] pyridine derivatives using multicomponent reaction strategy by microwave irradiation of 4-amino 2-oxo-2H-chromene, aromatic aldehydes and substituted anilines. This synthetic strategy was found to be very useful as it follows environment benign protocol, also it gives good outcome in terms of yield and requires shorter reaction time.

scholarly journals Pyridine Derivatives—A New Class of Compounds That Are Toxic to E. coli K12, R2–R4 Strains

Materials ◽  
2021 ◽  
Vol 14 (18) ◽  
pp. 5401
Author(s):  
Dominik Koszelewski ◽  
Ryszard Ostaszewski ◽  
Paweł Śmigielski ◽  
Anastasiia Hrunyk ◽  
Karol Kramkowski ◽  
...  
Keyword(s):  
Aromatic Aldehydes ◽  
Pyridine Derivatives ◽  
Antimicrobial Drugs ◽  
One Pot ◽  
Bacterial Dna ◽  
E Coli ◽  
New Class ◽  
Oxidative Damages ◽  
Preliminary Study ◽  
Selection Of

A preliminary study of 2-amino-4-aryl-3,5-dicarbonitrile-6-thiopyridines as new potential antimicrobial drugs was performed. Special emphasis was placed on the selection of the structure of target pyridine derivatives with the highest biological activity against different types of Gram-stained bacteria by lipopolysaccharide (LPS). Herein, Escherichia coli model strains K12 (without LPS in its structure) and R2–R4 (with different lengths of LPS in its structure) were used. Studied target compounds were provided with yields ranging from 53% to 91% by the lipase-catalyzed one pot multicomponent reaction of various aromatic aldehydes with malononitrile, and thiols. The presented work showed that the antibacterial activity of the studied pyridines depends on their structure and affects the LPS of bacteria. Moreover, the influence of the pyridines on bacteria possessing smooth and rough LPS and oxidative damage to plasmid DNA caused by investigated compounds was indicated. Additionally, the modification of the bacterial DNA with the tested compounds was performed to detect new potential oxidative damages, which are recognized by the Fpg protein. The obtained damage modification values of the analyzed compounds were compared with the modifications after antibiotics were used in this type of research. The presented studies demonstrate that 2-amino-4-aryl-3,5-dicarbonitrile-6-thiopyridines can be used as substitutes for known antibiotics. The observed results are especially important in the case of the increasing resistance of bacteria to various drugs and antibiotics.

scholarly journals Three-Dimensional Walnut-Like, Hierarchically Zn-MOF Microsphere: One-Pot Synthesis, Characterization And Its Application as a Green Catalyst For The Asymmetric Hantzsch Synthesis of Polyhydroquinolines

2021 ◽  
Author(s):  
Sayed Mohammad Ramish ◽  
Arash Ghorbani-Choghamarani ◽  
Masoud Mohammadi
Keyword(s):  
Hydrothermal Reaction ◽  
Three Dimensional ◽  
Aromatic Aldehydes ◽  
Zinc Salt ◽  
Tridentate Ligand ◽  
Selective Synthesis ◽  
Electronic Effects ◽  
One Pot ◽  
Physico Chemical ◽  
Bet Analysis

Abstract A three-dimensional walnut-like, microsphere Zn-based MOFs system was designed and synthesized via hydrothermal reaction of zinc salt with 4,6-diamino-2-pyrimidinethiol as a tridentate ligand. Besides, Zn ions were coordinated to the ligand’s functional groups to give a novel Zn-MOF microsphere material. Afterward, the resultant material was thoroughly characterized by various analysis and physico-chemical methods; including, FT-IR, XRD, TGA, EDX, X-ray mapping, SEM, TEM, and BET analysis. The Zn-MOF microspheres were utilized in the Hantzsch reaction for selective synthesis of asymmetric polyhydroquinolines, using various aromatic aldehydes. Our strategy provides a way for controlled synthesis of the hierarchically nanoporous Zn-MOF microspheres with well-defined morphology, structure, and excellent catalytic properties, resulting in having a promising heterogeneous catalyst for a selective synthesis with good yields in the short reaction time and a low limit of steric hindrance and electronic effects. Besides, the heterogeneity of the catalyst is further tested with hot filtration and also the reusability results point.

One-pot cis-selective route to sugar-fused thiazines via a masking–unmasking strategy in basic ionic liquid

2016 ◽  
Vol 94 (10) ◽  
pp. 827-832 ◽  
Author(s):  
Vijai K. Rai ◽  
Rahul K. Kosta
Keyword(s):  
Ionic Liquid ◽  
Amino Acid ◽  
Knoevenagel Condensation ◽  
Selective Synthesis ◽  
Ring Transformation ◽  
One Pot ◽  
Transformation Reaction ◽  
Basic Ionic Liquid ◽  
Ring Transformation Reaction ◽  
Cis Isomer

A novel sequential Knoevenagel condensation, thia-Michael, and amino/mercaptoacetylative ring transformation reaction cascade for cis-selective synthesis of sugar-fused 1,3-thiazine is reported. The expeditious one-pot multicomponent annulation was performed using masked amino acid viz. 2-phenyl-1,3-oxazol-5-one or masked mercaptoacid viz. 2-methyl-2-phenyl-1,3-oxathiolan-5-one, d-xylose/d-glucose, and N-aryldithiocarbamic acid in ionic liquid [bmim]OH. The acetophenone obtained as a by-product and [bmim]OH itself could be easily recycled for further use without loss of efficiency. The envisaged method is operationally simple, high yielding, and excellent diastereoselective in favor of the cis-isomer of fused thiazines.

Metal-, and Organocatalyst-Free One-Pot Assembly of Chiral Aza-Tricyclic Molecules: Creating Six Contiguous Stereocenters from 2-D-Structures and an Amino Acid

2020 ◽  
Author(s):  
Dung Do
Keyword(s):  
Amino Acid ◽  
Chemical Space ◽  
Structural Diversity ◽  
Therapeutic Agents ◽  
Chiral Molecules ◽  
One Pot ◽  
Complex Molecules ◽  
Chiral Catalyst ◽  
Chiral Complex ◽  
Free Process

<p>Chiral molecules with their defined 3-D structures are of paramount importance for the study of chemical biology and drug discovery. Having rich structural diversity and unique stereoisomerism, chiral molecules offer a large chemical space that can be explored for the design of new therapeutic agents.<sup>1</sup> Practically, chiral architectures are usually prepared from organometallic and organocatalytic processes where a transition metal or an organocatalyst is tailor-made for desired reactions. As a result, developing a method that enables rapid assembly of chiral complex molecules under metal- and organocatalyst-free condition represents a daunting challenge. Here we developed a straightforward route to create a chiral 3-D structure from 2-D structures and an amino acid without any chiral catalyst. The center of this research is the design of a <a>special chiral spiroimidazolidinone cyclohexadienone intermediate</a>, a merger of a chiral reactive substrate with multiple nucleophillic/electrophillic sites and a transient organocatalyst. <a>This unique substrate-catalyst (“subcatalyst”) dual role of the intermediate enhances </a><a>the coordinational proximity of the chiral substrate and catalyst</a> in the key Aza-Michael/Michael cascade resulting in a substantial steric discrimination and an excellent overall diastereoselectivity. Whereas the “subcatalyst” (hidden catalyst) is not present in the reaction’s initial components, which renders a chiral catalyst-free process, it is strategically produced to promote sequential self-catalyzed reactions. The success of this methodology will pave the way for many efficient preparations of chiral complex molecules and aid for the quest to create next generation of therapeutic agents.</p>

Chlorosulfonic Acid Supported Piperidine-4-carboxylic Acid (PPCA) Functionalized Fe3O4 Nanoparticles (Fe3O4-PPCA): The Efficient, Green and Reusable Nanocatalyst for the Synthesis of Pyrazolyl Coumarin Derivatives under Solvent-Free Conditions

2019 ◽  
Vol 22 (2) ◽  
pp. 123-128
Author(s):  
Setareh Habibzadeh ◽  
Hassan Ghasemnejad-Bosra ◽  
Mina Haghdadi ◽  
Soheila Heydari-Parastar
Keyword(s):  
Carboxylic Acid ◽  
Fe3o4 Nanoparticles ◽  
High Efficiency ◽  
Reaction Times ◽  
Chlorosulfonic Acid ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Magnetic Nanocatalyst ◽  
One Pot ◽  
Solvent Free Conditions

Background: In this study, we developed a convenient methodology for the synthesis of coumarin linked to pyrazolines and pyrano [2,3-h] coumarins linked to 3-(1,5-diphenyl-4,5- dihydro-1H-pyrazol-3-yl)-chromen-2-one derivatives using Chlorosulfonic acid supported Piperidine-4-carboxylic acid (PPCA) functionalized Fe3O4 nanoparticles (Fe3O4-PPCA) catalyst. Materials and Methods:: Fe3O4-PPCA was investigated as an efficient and magnetically recoverable Nanocatalyst for the one-pot synthesis of substituted coumarins from the reaction of coumarin with a variety of aromatic aldehydes in high to excellent yield at room temperature under solvent-free conditions. The magnetic nanocatalyst can be easily recovered by applying an external magnet device and reused for at least 10 reaction runs without considerable loss of reactivity. Results and Conclusion: The advantages of this protocol are the use of commercially available materials, simple and an inexpensive procedure, easy separation, and an eco-friendly procedure, and it shows good reaction times, good to high yields, inexpensive and practicability procedure, and high efficiency.

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