An efficient synthesis of imidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxides by a one-pot, three-component reaction in water

2018 ◽  
Vol 24 (6) ◽  
pp. 297-302 ◽  
Author(s):  
Jabbar Khalafy ◽  
Nasser Etivand ◽  
Neda Khalillou
Keyword(s):  
Reaction Times ◽  
Sulfamic Acid ◽  
One Pot ◽  
Green Protocol ◽  
H Nmr ◽  
Three Component Reaction ◽  
Ft Ir ◽  
High Yields ◽  
Reaction In Water ◽  
C Nmr

Abstract An improved synthesis of 2-ethyl-5-(2-hydroxy-4-oxoquinolin-3(4H)-ylidene)-6-aryl-5,6-dihydroimidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxide derivatives 4a–k via the reaction of aryl glyoxal monohydrates 1a–k, quinoline-2,4-diol 2 and 2-amino-[1,3,4]thiadiazole (3) in the presence of Et3N/sulfamic acid in H2O is described. This green protocol is characterized by the use of the readily available catalyst and reactants, short reaction times, operational simplicity and high yields of products. The structures of all compounds were characterized by 1H NMR, 13C NMR and Fourier-transform infrared (FT-IR) spectral data and microanalyses.

Ultrasound-assisted aqua-mediated synthesis of multi-substituted tetrahydropyridine-3-carboxylates using N-carboxymethyl-3-pyridinium hydrogensulfate ([N-CH2CO2H-3-pic]+HSO4−) as a new efficient ionic liquid catalyst

2021 ◽  
Vol 3 (6) ◽  
Author(s):  
Kobra Nikoofar ◽  
Fatemeh Shahriyari
Keyword(s):  
Ionic Liquid ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
H Nmr ◽  
Sonic Waves ◽  
Ft Ir ◽  
High Yields ◽  
Work Up ◽  
C Nmr

AbstractA simple, straightforward, and ultrasound-promoted method for the preparation of some highly functionalized tetrahydropyridines reported via pseudo five-component reaction of (hetero)aromatic aldehydes, different anilines, and alkyl acetoacetates in the presence of [N-CH2CO2H-3-pic]+HSO4−, as a novel ionic liquid, in green aqueous medium. The IL was synthesized utilizing simple and easily-handled substrates and characterized by FT-IR, 1H NMR, 13C NMR, GC-MASS, FESEM, EDX, and TGA/DTG techniques. The procedure contains some highlighted aspects which are: (a) performing the MCR in the presence of aqua and sonic waves, as two main important and environmentally benign indexes in green and economic chemistry, (b) high yields of products within short reaction times, (c) convenient work-up procedure, (d) preparing the new IL via simple substrates and procedure.

scholarly journals Para toluenesulfonic acid-catalyzed one-pot, three-component synthesis of benzo[5,6]chromeno[3,2-c]quinoline compounds in aqueous medium

2021 ◽  
Vol 27 (1) ◽  
pp. 90-99
Author(s):  
Naser Sadeghpour Orang ◽  
Hadi Soltani ◽  
Mehdi Ghiamirad ◽  
Mehdi Ahmadi Sabegh
Keyword(s):  
Thermal Conditions ◽  
Reaction Conditions ◽  
One Pot ◽  
Mass Spectral ◽  
H Nmr ◽  
Toluenesulfonic Acid ◽  
Ft Ir ◽  
High Yields ◽  
Arylglyoxal Monohydrates ◽  
C Nmr

Abstract A new series of benzo[5,6]chromeno[3,2-c]quinoline derivatives were successfully synthesized using various arylglyoxal monohydrates, quinoline-2,4-dione, and β-naphthol in H2O:EtOH (2:1) as a green solvent in the presence of catalytic amounts p-toluenesulfonic acid as a mild catalyst under reflux conditions with high yields (83–92%). The reaction conditions were optimized in different solvents at variable thermal conditions, and the optimized reaction condition for this synthesis has been reported. The structures of all new products were defined by 1H-NMR, 13C-NMR, FT-IR, mass spectral data, and HRMS.

scholarly journals A facile and one-pot synthesis of new tetrahydrobenzo[b]pyrans in water under microwave irradiation

BMC Chemistry ◽  
2019 ◽  
Vol 13 (1) ◽  
Author(s):  
Mandlenkosi Robert Khumalo ◽  
Surya Narayana Maddila ◽  
Suresh Maddila ◽  
Sreekantha B. Jonnalagadda
Keyword(s):  
Microwave Irradiation ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
One Pot ◽  
Spectral Techniques ◽  
H Nmr ◽  
Water As Solvent ◽  
Aqueous Solvent ◽  
Three Component Reaction ◽  
C Nmr

AbstractEleven new tetrahydrobenzo[b]pyran derivatives were synthesized via a three component reaction of different aromatic aldehydes, methyl cyanoacetate and 1,3-cyclohexadione, with water as solvent under catalyst-free microwave irradiation. The structures of all the new molecules were well analysed and their structures established by using various spectral techniques (1H NMR, 13C NMR, 15N NMR and HRMS). Various advantages of reported protocol are the ease of preparation, short reaction times (10 min), aqueous solvent and excellent yields (89–98%). Additionally, this method provides a clean access to the desired products by simple workup.

A highly efficient and green approach for the synthesis of pyrimido[4,5-b]quinolines using N,N-diethyl-N-sulfoethanaminium chloride

2021 ◽  
Vol 76 (2) ◽  
pp. 85-90
Author(s):  
Abdolkarim Zare ◽  
Manije Dianat
Keyword(s):  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Catalyst Amount ◽  
Green Protocol ◽  
Highly Efficient ◽  
Green Approach ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields

Abstract A highly efficient and green protocol for the synthesis of pyrimido[4,5-b]quinolines has been described. The one-pot multicomponent reaction of dimedone with arylaldehydes and 6-amino-1,3-dimethyluracil in the presence of N,N-diethyl-N-sulfoethanaminium chloride ([Et3N–SO3H][Cl]) as an ionic liquid (IL) catalyst under solvent-free conditions afforded the mentioned compounds in high yields and short reaction times. Our protocol is superior to many of the reported protocols in terms of two or more of these factors: the reaction times, yields, conditions (solvent-free versus usage of organic solvents), temperature and catalyst amount.

scholarly journals Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives

2014 ◽  
Vol 2014 ◽  
pp. 1-4 ◽  
Author(s):  
Hamid Beyzaei ◽  
Reza Aryan ◽  
Zahra Keshtegar
Keyword(s):  
Ring Opening ◽  
Reaction Times ◽  
Reaction Conditions ◽  
Ir Spectrometry ◽  
H Nmr ◽  
Chemical Structures ◽  
Thioamide Group ◽  
Solvent Free Conditions ◽  
Ft Ir ◽  
C Nmr

Synthesis of new imidazolidine and tetrahydropyrimidine derivatives 3a, b and 4a–c as cyclic 1,3-diamines under two reaction conditions (A and B) is described. Under reaction conditions-A, a suspension of (E)-2-cyano-2-(oxazolidin-2-ylidene)ethanethioamide 1 (1 eq.) and diaminoalkanes 2a–e (2 eq.) in absolute ethanol is heated under reflux for 16–22 h to afford 3a, b and 4a–c. Alternatively, under reaction conditions-B, a solution of thioamide 1 (1 eq.) in diaminoalkanes 2a–e (3 eq.) is stirred under solvent-free conditions at room temperature for 3 days to give desired products. Reaction conditions-A for having higher yields, shorter reaction times, and required less diamines is more effective than reaction conditions-B. Oxazolidine ring opening is observed by reacting compound 1 with all of the diamines 2a–e, but the thioamide group only reacts with nonbulky diamines 2a, b. The chemical structures of novel compounds were confirmed by 1H NMR, 13C NMR, elemental analysis, and FT-IR spectrometry.

scholarly journals Synthesis and Spectroscopic Characterization of Some New Biological Active Azo–Pyrazoline Derivatives

2012 ◽  
Vol 9 (3) ◽  
pp. 1613-1622 ◽  
Author(s):  
Farouq E. Hawaiz ◽  
Mohammad K. Samad
Keyword(s):  
Addition Reaction ◽  
Coupling Reaction ◽  
Spectroscopic Characterization ◽  
Hydroxyl Group ◽  
Significant Activity ◽  
H Nmr ◽  
Ft Ir ◽  
High Yields ◽  
C Nmr

A number of 3-[4-(benzyloxy)-3-(2-Chlorophenylazo)-phenyl]-5-(substituted-phenyl)-1-substituted-2-pyrazolines( 4a-j) and (5a-j) have been synthesized by diazotization of 2-chloroaniline and its coupling reaction with 4-hydroxy acetophenone, followed by benzyloxation of the hydroxyl group to give the substrate [4-benzyloxy-3-(2-chlorophenylazo)-acetophenone (1)].The prepared starting material (1) has been reacted with different substituted benzaldehydes to give a new series of chalcone derivatives 1-[(4-benzyloxy)-3-(2-chloro-phenylazo)-phenyl]-3-(substituted phenyl)-2-propen-1-one (3a-j), in high yields and in a few minutes, and the later compounds were treated with hydrazine hydrate according to Michael addition reaction to afford a new biolological active target compounds (4a-j) and (5a-j). Furthermore, The structures of the newly synthesized compounds were confirmed by FT-IR,13C-NMR,13C-DEPT &1H-NMR spectral data. The chalcone and pyrazoline derivatives were evaluated for their anti bacterial activity againstEscherichia colias gram negative andStaphylococcus aureusas gram positive, the results showed significant activity against both types of bacteria.

scholarly journals Microwave-Assisted Hydrogenation of Codeine in Aqueous Media

2012 ◽  
Vol 2012 ◽  
pp. 1-4 ◽  
Author(s):  
F. Taktak ◽  
I. Bulduk
Keyword(s):  
Aqueous Solution ◽  
Aqueous Media ◽  
One Pot ◽  
H Nmr ◽  
Microwave Assisted ◽  
Analysis Technique ◽  
Purity Analysis ◽  
Ft Ir ◽  
Elemental Analysis Technique ◽  
C Nmr

An efficient one-pot microwave-assisted hydrogenation of codeine was achieved in aqueous solution. This technique is simple, fast, environmentally friendly, and highly efficient. Structure of produced dihydrocodeine was approved by using FT-IR, 1H NMR, 13C NMR, EIMS, and elemental analysis technique. Its purity analysis was performed by using HPLC and assay analysis was performed by using potentiometric titration methods.

scholarly journals One-pot, three-component synthesis of pyrrolo[2,3-d]pyrimidine derivatives

2018 ◽  
Vol 62 (1) ◽  
Author(s):  
Jabbar Khalafy ◽  
Ramin Javahershenas
Keyword(s):  
Simple Procedure ◽  
Reaction Times ◽  
Pyrimidine Derivatives ◽  
Reaction Conditions ◽  
One Pot ◽  
General Applicability ◽  
Green Approach ◽  
Three Component Reaction ◽  
High Yields ◽  
Work Up

<p>A green approach for the synthesis of polyfunctionalized pyrrolo[2,3-<em>d</em>]pyrimidine derivatives was successfully achieved by a one-pot, three-component reaction of arylglyoxals, 6-amino-1,3-dimethyluracil and barbituric acid derivatives in the presence of tetra-<em>n</em>-butylammonium bromide (TBAB) (5 mol%) as the catalyst in ethanol at 50 °C. This protocol has many advantages such as high yields (73-95%), green and simple procedure, short reaction times, easy work-up, mild reaction conditions and general applicability.</p>

The Discovery of Ultrasound Irradiation as a Useful Tool for Accelerating Petasis Three-component Reaction: Synthesis of α-Arylglycines

2018 ◽  
Vol 15 (2) ◽  
pp. 256-266 ◽  
Author(s):  
Fan Yun ◽  
Chunhui Cheng ◽  
Jingxuan Li ◽  
Pingwah Tang ◽  
Qipeng Yuan
Keyword(s):  
Reaction Time ◽  
Glyoxylic Acid ◽  
Reaction Times ◽  
Ultrasound Irradiation ◽  
Secondary Amines ◽  
One Pot ◽  
Petasis Reaction ◽  
Three Component Reaction ◽  
Wide Range ◽  
High Yields

Aim and Objective: α-Arylglycines belong to an important class of non-proteinogenic amino acids. Petasis 3-component, one-pot reaction lends itself to be suitable for the synthesis of α-Arylglycines. Because of the low reactivity, Petasis reaction requires long reaction time. Our objective is to use ultrasound irradiation to accelerate this versatile Petasis' synthesis of α-Arylglycines. Materials and Methods: Ultrasound irradiation as a physical tool to accelerate the Petasis 3-component reaction without any auxiliary catalyst can significantly shorten the reaction time. The operation is simple. It can be applied to a wide range of substrates. In order to highlight the remarkable utility of the ultrasound in Petasis reaction, we have compared side-by-side the reactivity between the reaction with ultrasound and the one without ultrasound. Results: Using ultrasound, the reaction times of Petasis reactions with various amine substrates including primary and secondary amines, heterocyclic amines, with a wide variety of boronic acids having different substituents (activating and deactivating groups) in the phenyl rings, and with glyoxylic acid and salicylic aldehyde were shortened from 5 to more than 20-fold. Conclusion: We have discovered the first examples of an efficient ultrasound-promoted approach for Petasis reaction to prepare a series of α-arylglycines in high yields and in excellent purities. The low reactivity of the reactions in this study were significantly enhanced by the ultrasound irradiation. By virtue of the acceleration and the operational simplicity, the present ultrasound assisted Petasis reaction can find applications in the synthetic areas of the already widely used Petasis three-component reaction.

Synthesis and Characterization of Imidazo[1,2-a]Pyrimidine

2015 ◽  
Vol 52 ◽  
pp. 1-4
Author(s):  
A.M. Shah ◽  
A.J. Rojivadiya
Keyword(s):  
Mass Spectroscopy ◽  
Synthesis And Characterization ◽  
Spectroscopic Techniques ◽  
One Pot ◽  
H Nmr ◽  
Ft Ir ◽  
C Nmr

An efficient protocol for the synthesis of imidazo [1,2-a] pyrimidine was developed by using three component one-pot Biginelli synthesis. The synthesized compounds were characterized by spectroscopic techniques like FT-IR, 1H NMR, 13C NMR, and mass spectroscopy.

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