Synthesis of Zingerone Using NiCl2•6H2O-NaBH4 as a Selective Hydrogenation Reaction Agent

2019 ◽  
Vol 948 ◽  
pp. 127-132
Author(s):  
Murdiah ◽  
Deni Pranowo ◽  
Tri Joko Raharjo
Keyword(s):  
Mild Condition ◽  
Selective Hydrogenation ◽  
Aldol Condensation ◽  
Condensation Reaction ◽  
Hydrogenation Reaction ◽  
Second Step ◽  
H Nmr ◽  
Ft Ir ◽  
High Yields ◽  
C Nmr

Synthesis of zingerone (4-(4-hydroxy-3-methoxyphenyl)-2-butanone) has been done. The first step was to synthesize the compound (4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-on) through a cross aldol condensation reaction between vanilin:acetone mol ratio of 1:5:5, for 5 hours in high yields (97%). The second step was the selective hydrogenation of (4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-on) with NiCl2•6H2O-NaBH4 catalyst in mild condition. Based on the FT-IR, 13C-NMR and 1H-NMR and GC-MS analyses, the synthesis of zingerone has been successfully synthesized by selective hydrogenation reaction with 80% yield.

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 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 Synthesis of Thiophenyl Thiazole Based Novel Quinoxaline Derivatives

2015 ◽  
Vol 51 ◽  
pp. 115-124
Author(s):  
Haresh G. Kathrotiya ◽  
Yogesh T. Naliapara
Keyword(s):  
Aromatic Amine ◽  
Elemental Analysis ◽  
Condensation Reaction ◽  
High Yield ◽  
Experimental Procedure ◽  
H Nmr ◽  
Quinoxaline Derivatives ◽  
Ft Ir ◽  
C Nmr

A new series of thiophenyl thiazole based novel quinoxaline derivatives 4a-4t have been synthesized by base catalysed condensation reaction. In which 6-substituted 2,3-dichloroquinoxaline 1a and 4-(thiophen-2-yl) thiazol-2-amine 2b reacted in basic condition to afford intermediate 3c which reacts with various aromatic amine to form final compounds. Easy experimental procedure, high yield, and selectivity are the imperative features of this method. The identity of all the compounds has been established by 1H NMR, 13C NMR, FT-IR, and elemental analysis.

Synthesis of 4-(5-Bromo-4-Hydroxyphenyl-3-Methoxy)-2-Butanone and the Activity Test as Fruit Flies Attractant

2020 ◽  
Vol 840 ◽  
pp. 113-117
Author(s):  
Yuri Pradika ◽  
Deni Pranowo ◽  
Sabirin Matsjeh
Keyword(s):  
Aldol Condensation ◽  
Fruit Fly ◽  
Hydrogenation Reaction ◽  
Reduction Reaction ◽  
Fruit Flies ◽  
Base Catalyst ◽  
H Nmr ◽  
Activity Test ◽  
Ft Ir ◽  
Potential Test

Synthesis of 4-(5-bromo-4-hydroxyphenyl-3-methoxy)-2-butanone and its potential test as fruit flies attractant has been done. All of products were analyzed by FT-IR GC-MS, and 1H-NMR. Synthesis of 4-(5-bromo-4-hydroxyphenyl-3-methoxy)-2-butanone was carried out in three steps reaction. First, the bromination of vanillin was performed using KBrO3 and HBr in acidic condition. Second, aldol condensation of 5-bromovanillin with acetone using base catalyst NaOH 20%. Third, 4-(5-bromo-4-hydroxyphenyl-3-methoxy)-2-butanone was synthesized by reacting the reduction reaction of condensation aldol products with NaBH4 and NiCl2.6H2O in methanol solvent in mild condition. Based on FT-IR, GC-MS and 1H-NMR analyses, the synthesis of 4-(5-bromo-4-hydroxyphenyl-3-methoxy)-2-butanone has been successfully by selective hydrogenation reaction with 68% yield. Testing the result as attractant of fruit fly indicated that synthesized compound can be used as attractant.

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 Synthesis and Antimicrobial Activity of Some New Thiazolidin-4-one Derivatives of 4-(6-methylbenzo[d]thiazol-2-yl)benzamine

2013 ◽  
Vol 2013 ◽  
pp. 1-6
Author(s):  
Awaz Jamil Hussein ◽  
Hashim Jalal Azeez
Keyword(s):  
Escherichia Coli ◽  
Antimicrobial Activity ◽  
Significant Activity ◽  
Gram Negative ◽  
H Nmr ◽  
Cyclocondensation Reaction ◽  
Ft Ir ◽  
High Yields ◽  
Derivatives Of ◽  
C Nmr

A number of derivatives of 2-(substituted phenyl)-3-(4-(6-methylbenzo[d]thiazol-2-yl)phenyl) thiazolidin-4-one (3a–j) have been synthesized from the reaction of 4-(6-methylbenzo[d]thiazol-2-yl)benzenamine(1), with different substituted benzaldehydes (2a–j), followed by cyclocondensation reaction of the prepared imines with 2-meraptoacetic acid in high yields. Furthermore, the structures of the newly synthesized compounds were confirmed by FT-IR,13C-NMR,13C-DEPT, and1H-NMR spectral data. The imines and thiazolidin-4-one derivatives were evaluated for their antibacterial activity againstEscherichia colias gram negative andStaphylococcus aureusas gram positive, the results have shown significant activity against both types of bacteria.

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.

scholarly journals Synthesis of some New Quinoxalines Bearing Pyridinyl Thiazole Moiety

2015 ◽  
Vol 52 ◽  
pp. 74-83
Author(s):  
Haresh G. Kathrotiya ◽  
Yogesh T. Naliapara
Keyword(s):  
Elemental Analysis ◽  
Condensation Reaction ◽  
Mass Spectral Data ◽  
Structural Class ◽  
Mass Spectral ◽  
H Nmr ◽  
Chemical Structures ◽  
Quinoxaline Derivatives ◽  
Ft Ir ◽  
C Nmr

Keeping the objective to build up a new structural class of quinoxaline, a new series of quinoxaline derivatives bearing the pyridinyl thiazole nucleus have been synthesized by base-catalyzed chloro-amine condensation reaction approach. The protocol offers expeditious and easy synthesis with excellent yield. The chemical structures of the synthesized compounds were elucidated by 1H NMR, 13C NMR, FT-IR, elemental analysis, and mass spectral data.

scholarly journals Facile synthesis of new pyrazolo[4′,3′:5,6]pyrano[2,3-d]pyrimidin-5(1H)-ones via the tandem intramolecular Pinner–Dimroth rearrangement and their antibacterial evaluation

2019 ◽  
Vol 74 (2) ◽  
pp. 175-181
Author(s):  
Nadieh Dorostkar-Ahmadi ◽  
Abolghasem Davoodnia ◽  
Niloofar Tavakoli-Hoseini ◽  
Hossein Behmadi ◽  
Mahboobeh Nakhaei-Moghaddam
Keyword(s):  
Staphylococcus Epidermidis ◽  
Diffusion Method ◽  
Dimroth Rearrangement ◽  
Disk Diffusion Method ◽  
Gram Positive Bacteria ◽  
H Nmr ◽  
Ft Ir ◽  
High Yields ◽  
Aliphatic Carboxylic Acids ◽  
C Nmr

AbstractSome new 7-alkyl-4,6-dihydropyrazolo[4′,3′:5,6]pyrano[2,3-d]pyrimidin-5(1H)-ones were prepared through heterocyclization of 6-amino-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles with aliphatic carboxylic acids in the presence of phosphoryl chloride under reflux in high yields. The suggested mechanism involves a tandem intramolecular Pinner–Dimroth rearrangement. The products were characterized on the basis of FT-IR, 1H NMR, and 13C NMR spectral and microanalytical data and evaluated for their antibacterial activity against Gram-positive bacteria (Staphylococcus aureus and Staphylococcus epidermidis) and Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) using the disk diffusion method.

scholarly journals Synthesis and antioxidant properties of 2-(3-(hydroxyimino)methyl)-1H-indol-1-yl)acetamide derivatives

2020 ◽  
Vol 6 (1) ◽  
Author(s):  
Chandravadivelu Gopi ◽  
Magharla Dasaratha Dhanaraju
Keyword(s):  
Antioxidant Activity ◽  
Condensation Reaction ◽  
Antioxidant Properties ◽  
Side Chain ◽  
Antioxidant Power ◽  
H Nmr ◽  
Antioxidant Agents ◽  
Phenyl Rings ◽  
Ferric Reducing Antioxidant Power ◽  
Ft Ir

Abstract Background The main aim of this work was to synthesise a novel N-(substituted phenyl)-2-(3-(hydroxyimino) methyl)-1H-indol-1-yl) acetamide derivatives and evaluate their antioxidant activity. These compounds were prepared by a condensation reaction between 1H-indole carbaldehyde oxime and 2-chloro acetamide derivatives. The newly synthesised compound structures were characterised by FT-IR, 1H-NMR, mass spectroscopy and elemental analysis. Furthermore, the above-mentioned compounds were screened for antioxidant activity by using ferric reducing antioxidant power (FRAP) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) methods. Result The antioxidant activity result reveals that most of the compounds were exhibiting considerable activity in both methods and the values are very closer to the standards. Among the synthesised compounds, compound 3j, 3a and 3k were shown remarkable activity at low concentration. Conclusion Compounds 3j, 3a and 3k were shown highest activity among the prepared analogues due to the attachment of halogens connected at the appropriate place in the phenyl ring. Hence, these substituted phenyl rings considered as a perfect side chain for the indole nucleus for the development of the new antioxidant agents.

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