Eco-friendly Synthesis of Some New Benzylidene-iminothiazolyl-pyrazol-3-ol Derivatives via One-Pot Multicomponent Reaction and Evaluation of Antioxidant Activities

2021 ◽  
Vol 6 (4) ◽  
pp. 264-269
Author(s):  
Ajay N. Ambhore
Keyword(s):  
Multicomponent Reaction ◽  
Antioxidant Activities ◽  
Bleaching Earth ◽  
Ethyl Cyanoacetate ◽  
Phenacyl Bromide ◽  
Mass Spectral Data ◽  
One Pot ◽  
Mass Spectral ◽  
Reaction Proceeds ◽  
Reaction Media

In present work, one-pot multicomponent reaction (MCR) route for the synthesis of benzylideneiminothiazolyl- pyrazol-3-ol derivatives (5a-p) by reacting ethyl cyanoacetate (1), substituted benzaldehyde (2a-c), thiosemicarbazide (3) and substituted phenacyl bromide (4a-g). This reaction proceeds by using bleaching earth clay (BEC) (pH 12.5) in PEG-400 as a green reaction media. All the synthesized compounds were characterized by IR, 1H NMR, 13C NMR and mass spectral data. The pharmacological investigation of the synthesized compounds suggest that most of them showed good antioxidant activity.

scholarly journals AN EFFICIENT THREE COMPONENT ONE-POT SYNTHESIS OF -1,2,3,4-TETRAHYDRO-4-OXO- 6-(5-SUBSTITUTED 2-PHENYL-1H-INDOL-3-YL)-2-THIOXOPYRIMIDINE-5-CARBONITRILE AS ANTIMICROBIAL AND ANTITUBERCULAR AGENTS

2021 ◽  
pp. 94-97
Author(s):  
PRABHAKER WALMIK
Keyword(s):  
Spectral Data ◽  
13C Nmr ◽  
Antitubercular Agents ◽  
Mass Spectral Data ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Spectral Techniques ◽  
Mass Spectral ◽  
One Pot Synthesis

Objective: The objective of the study was to synthesis of 1,2,3,4-tetrahydro-4-oxo-6-(5-substituted 2-phenyl-1H-indol-3-yl)-2-thioxopyrimidine-5- carbonitrile derivatives (4a-c). Methods: The structures of all these unknown compounds have been confirmed with the help of physical and spectral techniques such as IR, 1H, and 13C NMR and mass spectral data and these newly synthesized compounds were evaluated for in-vitro antimicrobial and antitubercular activities. Results: Screening studies have demonstrated that the newly synthesized compound 4a exhibited promising antimicrobial and antitubercular properties. Conclusion: The final results revealed that compound 4a exhibited promising antimicrobial and antitubercular properties when compared to the standard drugs.

scholarly journals Zinc Triflate Promoted General Synthetic Protocol for the Facile Construction of Chromenes and Pyrimidines Bearing N-Allyl Quinolone Nucleus

2015 ◽  
Vol 47 ◽  
pp. 199-207
Author(s):  
Nileshkumar D. Vala ◽  
Hardik H. Jardosh ◽  
Manish P. Patel
Keyword(s):  
Elemental Analysis ◽  
13C Nmr ◽  
Room Temperature ◽  
Mass Spectral Data ◽  
One Pot ◽  
Mass Spectral ◽  
Cyclocondensation Reaction ◽  
Ft Ir ◽  
Derivatives Of ◽  
Zinc Triflate

A series of 8 derivatives of chromene 5a-h synthesized via one-pot cyclocondensation reaction of N-allyl quinolones, α/β naphthol and malononitrile. And 8 derivatives of pyrimidines 8a-h bearing N-allyl quinolone have been synthesized by N-allyl quinolones, ethylacetoacetate, thiourea/urea in the presence of zinc triflate as less toxic catalyst. This methodology allowed the high conversion of product at room temperature. Titled derivatives were elucidated by FT-IR, 1H NMR, 13C NMR, elemental analysis, and mass spectral data.

scholarly journals A One Pot Synthesis of 5, 7-diaryl-1,5-dihydro (or 1, 2, 3, 5-tetrahydro)- pyrano[2, 3-D] pyrimidin-2, 4-diones (or 2-thioxo-4-ones)

2013 ◽  
Vol 61 (2) ◽  
pp. 167-171 ◽  
Author(s):  
M Mahbubur Rahman ◽  
S Mosaddeq Ahmed ◽  
SMA Hakim Siddiki ◽  
Md Ershad Halim ◽  
Kawsari Akhter ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Glacial Acetic Acid ◽  
Barbituric Acid ◽  
Thiobarbituric Acid ◽  
Mass Spectral Data ◽  
Phosphorous Pentoxide ◽  
One Pot ◽  
Mass Spectral ◽  
Elemental Analyses ◽  
One Step

A number of 5, 7-diaryl-1,5-dihydro (or 1, 2, 3, 5-tetrahydro)- pyrano[2, 3-d] pyrimidin-2, 4-diones (or 2-thioxo-4-ones) (3a-f) have been synthesized in one-step by cyclocondensation of barbituric acid or thiobarbituric acid (1) with arylideneacetophenones (2a-c), in glacial acetic acid in the presence of phosphorous pentoxide. The structures of the compounds 3a-f have been determined by UV, IR, 1H NMR, 13C NMR, mass spectral data and elemental analyses. DOI: http://dx.doi.org/10.3329/dujs.v61i2.17065 Dhaka Univ. J. Sci. 61(2): 167-171, 2013 (July)

scholarly journals A one-pot synthesis of 7,11-diaryl-2,4-diazaspiro[5,5]undecane-3-oxo (or thioxo)-1,5,9-triones

1970 ◽  
Vol 24 (2) ◽  
pp. 135-142
Author(s):  
M Giasuddin Ahmed ◽  
Syeda Asghari Ahmed ◽  
UKR Romman ◽  
Kawsari Akhter ◽  
Md Ershad Halim ◽  
...  
Keyword(s):  
Barbituric Acid ◽  
Aqueous Ethanol ◽  
Thiobarbituric Acid ◽  
Chemical Society ◽  
Spiro Compounds ◽  
Mass Spectral Data ◽  
One Pot ◽  
Mass Spectral ◽  
Ethanol Medium ◽  
Elemental Analyses

Spiro compounds 7,11-diaryl-2,4-diazaspiro[5,5]undecane-1,3,5,9-tetraones 3a-d were prepared by carrying out reactions between diarylideneacetones, (ArCH=CH)2C=O, 2a-d [Ar= 2-CH3C6H4, 4-CH3C6H4, 4-(CH3)2NC6H4 and 4-HOC6H4 respectively] and  barbituric acid (1a) under refluxing condition in aqueous ethanol medium without using any catalyst. Under similar conditions the corresponding 7,11-diaryl-3-thioxo-2,4-diazaspiro[5,5]undecane-1,5,9-triones 3e-g were synthesized from the reactions of diarylideneacetones 2a, 2d and 2e [Ar= 4-ClC6H4] with 2-thiobarbituric acid (1b). The structures of the spiro compounds were established with the help of their UV, IR, 1H NMR, 13C NMR and mass spectral data and elemental analyses. DOI: http://dx.doi.org/10.3329/jbcs.v24i2.9702 Journal of Bangladesh Chemical Society, Vol. 24(2), 135-142, 2011

scholarly journals A three step one-pot regioselective synthesis of highly substituted pyrazolo[1,5-a]pyrimidines assisted by KHSO4 in aqueous media under ultrasound irradiation

2020 ◽  
Vol 11 (3) ◽  
pp. 179-186
Author(s):  
Shunan Kaping ◽  
Philippe Helissey ◽  
Jai Narain Vishwakarma
Keyword(s):  
Aqueous Media ◽  
Ultrasound Irradiation ◽  
Mass Spectral Data ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Triclinic Space Group ◽  
X Ray ◽  
Mass Spectral ◽  
Chemical Structures ◽  
Crystallographic Study

A simple and efficient synthesis of substituted pyrazolo[1,5-a]pyrimidine derivatives has been developed by the use of ultrasound. 5-Methyl-4-phenyl-1H-pyrazol-3-amine required for the synthesis of pyrazolo[1,5-a]pyrimidine derivatives has been easily obtained by the reaction of 3-(dimethylamino)-2-phenylacrylonitrile (formed from readily available 2-phenylacetonitrile) with hydrazine hydrate in refluxing ethanol. The 5-aminopyrazole was then reacted with various formylated active proton compounds in presence of KHSO4 in aqueous medium under ultrasound irradiation to give the desired products. The chemical structures of the newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and Mass spectral data. X-ray crystallographic study of a selected compound 6-(4-chlorophenyl)-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine (7c) was performed to ascertain the regioselectivity of the reaction. Crystal data for compound 7c: Triclinic, space group P-1 (no. 2), a = 8.0198(3) Å, b = 14.0341(6) Å, c = 14.2099(6) Å, α = 87.672(2)°, β = 83.902(2)°, γ = 89.120(2)°, V = 1588.87(11) Å3, Z = 4, T = 293(2) K, μ(MoKα) = 0.248 mm-1, Dcalc = 1.400 g/cm3, 12918 reflections measured (4.012° ≤ 2Θ ≤ 49°), 5152 unique (Rint = 0.0411, Rsigma = 0.0429) which were used in all calculations. The final R1 was 0.0486 (I > 2σ(I)) and wR2 was 0.1320 (all data).

scholarly journals Synthesis of some biologically active 2,4'-bipyridine-5-carbonitriles carrying the 4-hydroxyphenylthio moiety

2009 ◽  
Vol 74 (7) ◽  
pp. 733-743 ◽  
Author(s):  
T. Karabasanagouda ◽  
Vasudeva Adhikari ◽  
G. Parameshwarappa
Keyword(s):  
13C Nmr ◽  
Ammonium Acetate ◽  
Ethyl Cyanoacetate ◽  
Aromatic Aldehydes ◽  
Biologically Active ◽  
The Other ◽  
Mass Spectral Data ◽  
1H And 13C Nmr ◽  
Mass Spectral

A series of new 4-aryl-2'-[(4-hydroxyphenyl)thio]-6oxo-1,6-dihydro- 2,4'-bipyridine-5-carbonitriles (3a-k) and 6-amino-4aryl-2'-[(4-hydroxyphenyl) thio]-2,4'-bipyridine-5-carbonitriles (4a-h) were synthesized from 4-hydroxythiophenol (1). The reaction of 4-hydroxythiophenol with 4-acetyl-2-chloropyridine yielded 1-{2-[(4-hydroxyphenyl)thio]pyridin-4-yl}ethanone (2). Further treatment of 2 with ethyl cyanoacetate in the presence of ammonium acetate with various aromatic aldehydes furnished the compounds 3a-k. On the other hand, condensation of 2 with aromatic aldehydes in the presence of alcoholic malononitrile in ammonium acetate gave compounds 4a-h. The structures of the newly synthesized compounds were established on the basis of their elemental analysis, as well as their IR, 1H- and 13C-NMR and mass spectral data. All the title compounds were subjected to in vitro antibacterial testing against two strains and antifungal screening against two fungi. Some of the compounds showed promising activity.

A Clean, Benign, Energy Efficient One-Pot Multicomponent Synthesis and Bio-evaluation of Novel [1,2,4]Triazolo[1,5-a]quinolines

2021 ◽  
Vol 6 (2) ◽  
pp. 111-115
Author(s):  
H.P. Parekh ◽  
M.H. Chauhan ◽  
N.L. Solanki ◽  
V.H. Shah
Keyword(s):  
Room Temperature ◽  
Cost Effective ◽  
Second Step ◽  
Mass Spectral Data ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Green Catalyst ◽  
Mass Spectral ◽  
Elemental Analyses ◽  
Ft Ir

In present work, a series of novel [1,2,4]triazolo[1,5-a]quinoline derivatives (HP-101-110) have been synthesized using multi-component reaction at room temperature in the presence of ammonium chloride as mild, cost effective green catalyst along with water as eco-friendly green solvent. The synthesis of 1,2,4-triazolo[1,5-a]quinolines (HP-101-110) was achieved by two step process. In first step, diversified Hantzsch pyridine reaction of an appropriate aromatic aldehyde, malononitrile, dimedone and benz hydrazide using ethanol as a solvent gives N-(2-amino-3-cyano-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8- tetrahydro-quinolin-1(4H)-yl)-4-hydroxybenzamide derivatives. In the second step, synthesis of the final product 2-(4-hydroxyphenyl)-8,8-dimethyl-6-oxo-5-phenyl-6,7,8,9-tetrahydro[1,2,4]triazolo[1,5- a]-quinoline-4-carbonitriles was achieved by the intramolecular cyclization of step 1 product.The structure of all the synthesized compounds (HP101-110) has been elucidated by FT-IR, 1H & 13C NMR, mass spectral data and elemental analyses.

scholarly journals Design, Synthesis, and In Vitro Antimicrobial Evaluation of Fused Pyrano[3,2-e]tetrazolo[1,5-c]pyrimidines and Diazepines

2013 ◽  
Vol 2013 ◽  
pp. 1-9 ◽  
Author(s):  
Sankari Kanakaraju ◽  
P. Sagar Vijay Kumar ◽  
Bethanamudi Prasanna ◽  
G. V. P. Chandramouli
Keyword(s):  
Carbon Disulfide ◽  
Phenacyl Bromide ◽  
Mass Spectral Data ◽  
Design Synthesis ◽  
Mass Spectral ◽  
H Nmr ◽  
Elemental Analyses ◽  
Antimicrobial Evaluation ◽  
C Nmr

A series of novel pyranochromene-containing tetrazoles fused with pyrimidinethiones, pyrimidines, and diazepines 3a–f, 4a–f, and 5a–f were synthesized by condensation of the corresponding tetrazoles 2a–f with carbon disulfide, benzaldehyde, and 4-methoxy phenacyl bromide, respectively. The compound 2a–f was obtained by reaction of pyrano[3,2-c]chromenes 1a–f with sodium azide. The structures of the newly synthesized compounds 2a–f to 5a–f were established on the basis of their elemental analyses, IR, 1H NMR, 13C NMR, and mass spectral data. All of the title compounds were subjected to in vitro antibacterial testing against four pathogenic strains and antifungal screening against two fungi. Preliminary results indicate that some of them exhibited promising activities and that they deserve more consideration as potential antimicrobials.

scholarly journals Microwave Induced Facile One-Pot Access to Diverse 2-Cyanobenzothiazole-A Key Intermediate for the Synthesis of Firefly Luciferin

2015 ◽  
Vol 44 ◽  
pp. 81-89 ◽  
Author(s):  
Neelam P. Prajapati ◽  
Rajesh H. Vekariya ◽  
Hitesh D. Patel
Keyword(s):  
Microwave Irradiation ◽  
Elemental Analysis ◽  
High Purity ◽  
Mass Spectral Data ◽  
One Pot ◽  
Mass Spectral ◽  
H Nmr ◽  
Solvent Free Conditions ◽  
Firefly Luciferin ◽  
One Step

An eco-friendly one-step preparation of various substituted 2-cyanobenzothiazole by condensation of corresponding substituted ortho-aminothiophenol with ethyl cyanoformate, employing an effective amount of Lawesson’s reagent, under microwave irradiation (MWI) and solvent free conditions is presented. The structures of the compounds were elucidated with the aid of elemental analysis, IR, 1H-NMR and mass spectral data. The targeted various substituted 2-cyanobenzothiazole are obtained in good yields and high purity.

scholarly journals One-pot synthesis of new Pyrido [2,3-d] Pyrimidine derivatives under ultrasonic irradiation using organo catalyst 4-Dimethylaminopyridine (DMAP)

2016 ◽  
Vol 3 (1) ◽  
Author(s):  
Imtiyaz Rasool Parrey ◽  
Athar Adil Hashmi
Keyword(s):  
Ultrasonic Irradiation ◽  
Aromatic Aldehydes ◽  
Major Effect ◽  
Mass Spectral Data ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Environment Friendly ◽  
Mass Spectral ◽  
One Pot Synthesis ◽  
The One

AbstractThe one-pot synthesis of pyrido[2,3-d] pyrimidine derivatives has been reported via Knoevenagel-Michal addition pathways using substituted aromatic aldehydes, Cyanoacetamide and 6-aminouracil in N,N-dimethylformamide (DMF) solvent, with 4-dimethylaminopyridine (DMAP) as new organo catalyst catalyst under ultrasonic irradiation. The results showed that a series of aromatic aldehydes were effectively used to prepare the targeted pyrido [2, 3-d] pyrimidine derivatives with good to excellent yields (81-93 %) with no major effect on the yield of product by electron donating/withdrawing substituents. Short reaction time, environment friendly procedure, excellent yields, inexpensive and readily available catalyst are the advantages of this procedure. All synthesized compounds were characterized by IR, 1HNMR, 13CNMR and mass spectral data.

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