The synthesized cycloadduct displayed a tendency to exhibit an imineenamine type of. Xiaoyong duan, xiulong yang, panpan jia, man zhang, bing han. Molecular docking studies of pyrazoline derivatives. The present study aims at the synthesis of pyrazolines bearing benzothiazole and their evaluation as anticancer agents. The mechanism begins with an acid catalyzed imine formation, where in the case of hydrazine derivatives the attack can happen on either carbonyl carbon and result in two possible. And then the synthesis of the novel compounds 7 were accomplished by the reaction of pyrazole and its derivatives 6a6f with the 2isocyanate glucose 5 to give the. Ethyl 1,2,4 triazolo3,4c1,2,4triazino5,6b5hindole5ethanoate 26 and 15h. Mar 21, 2007 effect of reaction condition on synthesis of 1,3,5triphenyl2pyrazoline a in order to verify the effect of ultrasound irradiation, in the absence of ultrasound, we have performed the reaction of chalcone with phenylhydrazine hydrochloride by refluxing at 108c for 4 h. Design, synthesis and biological evaluation of novel antitubercular agents by combining pyrazoline and benzoxazole pharmacophores hemal m.
The relationship of substituents and the optical properties were discussed. Nmr results suggests that only the rc snh 2 and rc onh 2 species, more stable, are present. An experimental study on the synthesis, tautomerism and acid promoted structural changes of spiropyrazolines is described. Beiqiong lu, jianming zhang, mingjian wang, yuanhai zhou, xiaolei chen. First, the chalcones were prepared fron substituted aldehydes and ketones in the presence of alkali naoh and alcohol as solvent medium. Based on the biological activities exhibited by the pyrazoline compounds, revanasiddappa32 et al. Synthesis, antimicrobial and antitubercular activities of. A proposed mechanism for formation of the pyrazole via spiropyrazoline ring opening is shown in scheme 3. Synthetic and biological studies of pyrazolines and.
As microwave irradiation facilitates the polarization of the molecule, the. Synthesis of pyrazoline derivative was performed in a manner as outlined in scheme 2 and 3. An ecofriendly synthesis of 2pyrazoline derivatives. A simple, efficient and environment friendly method has been developed for the synthesis of pyrazoline by the cyclocondensation of chalcones and hydrazine hydrate using very cheaper catalyst, bakers yeast saccharomyces cerevisiae. Bhandari, synthesis, antimicrobial and antitubercular activities of some novel pyrazoline derivatives, journal of saudi chemical society, vol. Synthesis, photoluminescence properties and theoretical insights on 1,3diphenyl59anthryl2 pyrazoline and 1hpyrazole.
Synthesis, antimicrobial and antitubercular activities of some novel. The title compound was prepared by reaction of e14tertbutoxyphenyl4,4dimethylpent1en3one e1 and 4fluorophenylhydrazine hydrochloride according to the general procedure for pyrazoline synthesis. Pyrazole is an aromatic heterocyclic compound characterized by a five membered ring with formula c 3 h 3 n 2 h. After the formation of the cycloadduct 11, an imine to enamine tautomerization occurs to form the enamine tautomer 12. Synthesis and fluorescent property of pyrazoline derivatives. Tuning the photoinduced electrontransfer thermodynamics in 1. Synthesis of pyrazoline derivatives from halovinylacetylenes and haloallenes. Synthesis, antibacterial and antifungal activity of some. Reaction of substituted acetophenones and benzaldehydes to form chalcones. The bispyrazoline derivatives 3ag were obtained by the reaction of compound 1 with substituted chalcone 2 in the alkaline ethanol solution under reflux temperature in 2034% yields. Based on the neuroprotective properties of 2pyrazoline derivatives, in the current work. Pyrazoline synonyms, pyrazoline pronunciation, pyrazoline translation, english dictionary definition of pyrazoline. Synthesis of pyrazoline derivatives from halovinylacetylenes. An ironcatalyzed route for the regioselective synthesis of 1,3 and 1,3,5substituted.
A series of 2pyrazolines 59 have been synthesized from. The 1 h nmr spectra of the compounds showed three doublet of doublets in the regions of. Tuning the photoinduced electrontransfer thermodynamics. Synthesis, antitubercular and analgesic activity evaluation of new 3pyrazoline derivatives. It forms white crystals or white crystalline powder.
Taj t, kamble rr,gireesh tm, hunnur rk and margankop sb. There are various green techniques available in the literature for synthesis of pyrazoline derivatives. The pyrazoline compounds 309 and their 1acetylated derivatives congiu et al. Experimental detail data which includes experimental detail of the spectral instruments, synthesis of 1,3,5triaryl2pyrazolines, 1 h nmr, c, ir and elemental analysis data along with ultrasonic instrument. A novel synthesis of 1,3,5trisubstituted pyrazoles through a. Pyrazoline is a heterocyclic chemical compound with the molecular formula c 3 h 6 n 2.
Synthesis and spectral characterization of novel 2pyrazoline. Kshirsagar2, sarita singhal1 1mahatma jyoti rao phoole university, jaipur, rajasthan, india 2p. The structures of these compounds were confirmed by. The synthesis of arylsubstituted pyrazolines 73 has been developed by matthias beller and coworkers alex et al. The structures of the compounds 3ag were determined by ir, 1 h nmr and hrms spectral data. A novel synthesis of 1,3,5trisubstituted pyrazoles. A series of donorsubstituted 1,3,5triaryl2pyrazoline fluorophores were structurally characterized by xray analysis, and their photophysical properties studied by steadystate absorption and emission spectroscopy.
Synthesis of different chalcones using substituted acetophenones and benzaldehydes. Since conventional methods of organic synthesis are energy. Synthesis, anticancer activity, and docking study of nacetyl. One pot synthesis of pyrazoline derivatised carbazoles as antitubercular, anticancer agents, their dna cleavage and antioxidant activities. These compounds were prepared by cyclocondensation of chalcones and bischalcones in presence of hydrazine hydrate. Then, addition of hydrazine hydrate afforded pyrazoline intermediates. Synthesis and evaluation of new pyrazoline derivatives as.
Parkinsons disease pd is a chronic, progressive, and agerelated neurodegenerative disorder characterized by the loss of midbrain dopaminergic neurons caused by the accumulation of free radicals and oxidative stress. An efficient synthesis of some new chalcone, acetyl pyrazoline and amino pyrimidine bearing 1,3,5triazine nucleus as potential antimicrobial and antitubercular agent. A series of new pyrazoline derivatives containing pyridine, piperazine and amide linkage were prepared through multistep synthesis. This reaction was conducted in formic acid in presence of bf3et2o or in acetic acid. The photoinduced electrontransfer thermodynamics of the derivatives was estimated on the basis of the spectroscopic data and redox potentials of. S ynthesis and characterization of pyrazoline derivatives. Cecl3 7h2o catalysed synthesis of 2pyrazoline derivatives 1443 1 2 3 510 c scheme 1. Synthesis of a series of pyrazoline derivatives carrying tosyl. Chemicals and reagent furan2carbaldehyde, various acetophenone, phenyl hydrazine, hydrazine hydrate, ethanol, ampicillin and griseofulvin. An efficient synthesis of some new chalcone, acetyl. This article about a heterocyclic compound is a stub. The sequence leading to the title compounds is outlined in scheme 1. The reaction of halovinylacetylenes and haloallenes with hydrazine and phenylhydrazine in the presence of a mixture of copper powder and cuprous chloride gives substituted pyrazolines. Ecofriendly synthesis of pyrazoline derivatives impact factor.
Pdf synthesis and anticonvulsant activity of some substituted 3,5. In order to quickly refresh your memory, a pyrrolelike nitrogen is a nonbasic nitrogen, with a lone pair involved. The cyclization of chalcones with phenyl hydrazine hydrochloride under basic condition in 50 ml of ethanol led to the formation of nphenyl pyrazoline compounds and it is stable in solid state. Synthesis of 3acetyl4hydroxyphenyl acetamide 1 a mixture of pacetamidophenol 0. Synthesis and antimicrobial activities of various pyrazolines from chalcones vishal d. Design, synthesis and biological evaluation of some novel. Their experiment seems to be the first example of pyrazoline formation by the reaction of an. It was cooled and poured onto crushed ice, filtered, washed with water and crystallized from acetone. Green synthesis of pyrazoline derivatives the design of chemical products and processes that are more environmentally benign and reduce negative impacts to human health and the environment16. Pdf synthesis and characterization of a novel 2pyrazoline. Apr 02, 2014 an experimental study on the synthesis, tautomerism and acid promoted structural changes of spiropyrazolines is described. Synthesis of 1,3,5trisubstituted2pyrazolines compound p 54fluorophenyl34fluorophenyl1isonicotinoylpyrazoline 9,10 was performed by taking equimolar quantities 0. E14ethoxycarbonylphenyl53,4dimethoxyphenyl33,4dimethoxystyryl2pyrazoline was synthesized via the cyclization reaction between the monocarbonyl curcuminoid 2e,6e2,6bis3,4dimethoxybenzylideneacetone and ethyl hydrazinobenzoate in high yield and purity 95% by highperformance liquid chromatography hplc.
Synthesis, xray crystal structure and optical properties. The mechanism begins with an acid catalyzed imine formation, where in the case of hydrazine derivatives the attack can happen on either carbonyl carbon. In summary, we report a unique route for the synthesis of novel 1,3,5trisubstituted pyrazoles through a novel 1,3dipolar cycloadditionring opening of a spiro pyrazoline intermediate. It is a pyrazoline derivative which is chemically 2,3dimethyl1phenyl 3pyrazolin5one.
A new series of benzothiazolepyrazoline hybrids 4ap were synthesized from condensation reaction of intermediate chalcones by cyclizing with phenyl hydrazine. New 2pyrazoline derivatives 15 bearing benzenesulfonamide moieties were then synthesized by condensing the appropriate chalcones 24 with 4hydrazinyl benzenesulfonamide hydrochloride. An i 2mediated metalfree oxidative cn bond formation enables a regioselective pyrazole synthesis. The structures of the newly synthesized compounds were confirmed by ir, 1h nmr, lcms and hplc elemental analysis. A onepot synthesis of nitrogencontaining heterocycles from alkyl dihalides and primary amines and hydrazines occurs under microwave irradiation via a simple and efficient cyclocondensation in an alkaline aqueous medium. Remove the stirrer and leave the reaction mixture in an ice chest or. We have recently explored the synthesis and antimicrobial activity of a series of compounds having aryloxy substituents attached to pyrazoline. During the last century, after these pioneering studies, numerous 2pyrazolines. With increasing the solvent polarity, fluorescence emission displayed a redshift and fluorescence quantum yields decreased. A strategy for the synthesis of pyrazolinefunctionalized oxindoles. Synthesis and pharmacological activities of pyrazole.
A strategy for the synthesis of pyrazoline functionalized oxindoles. All the compounds were stable in the solid as well as in the solution state. Udupi, himabindu 1, ajjanna m sridharav 3 1 department of chemistry, jawaharlal nehru technological university kukatpally, hyderabad 500072. Pdf synthesis and characterization of pyrazoline derivatives. The desired compounds were prepared by the reaction of 6,6dimethyl4oxo4,5,6,7tetrahydro1hindole2carbaldehyde 1 with different acetophenones. The synthesis of novel pyrazoline derivatives and investigation of their chemical and biological behavior have gained more improved potency and lesser toxicity.
Eight new compounds containing in their structures substituted quinoline and pyrazole entity were synthesized in good to excellent yield by cyclocondensation reaction of chalcones and hydrazine hydrate. These approaches were extended to bischalcones, which delivered functionalized. The new prepared compounds will contain both quinoline and pyrazoline moieties. Synthesis, antibacterial and antifungal activity of some new. Led by these considerations, it appeared of interest to synthesize novel pyrazoline derivatives and screened for their antimicrobial activities. Synthesis of ethyl 3,5substituteddiphenyl4,5dihydropyrazole1carboxylate derivatives c 1c 6. Instead of compound 12 reverting to 11, the enamine tautomer undergoes an eliminatory ring cleavage of the indoline ring at the spirocyclic carbon. Diversely substituted pyrazolines embedded with a variety of functional groups are found in many important biologicallyactive compounds and. Synthesis, spectroscopic and computational characterization. Synthesis of nheterocycles synthesis of pyrazolines.
Wadhwani college of pharmacy, yavatmal, maharashtra, india corres. The structures of nphenyl pyrazoline derivatives 7a. Pdf the chemistry of chalcones has generated intensive scientific studies throughout the world. The knorr pyrazole synthesis is an organic reaction used to convert a hydrazine or its derivatives and a 1,3dicarbonyl compound to a pyrazole using an acid catalyst. Download fulltext pdf download fulltext pdf download fulltext pdf synthesis and characterization of a novel 2pyrazoline article pdf available in molbank 20093 september 2009 with 673 reads. So, pertaining to its importance, many attempts are made to synthesize pyrazolines.
The compound of different pyrazoline derivatives were synthesized by cyclisation of substituted chalcone derivatives in the presence of 2, 4 dintro phenyl. Review on synthesis of bioactive pyrazoline derivatives. Feprazone also finds use in the treatment of rheumatic disorders. Synthetic and biological studies of pyrazolines and related. General procedure for the synthesis of pyrazolines 4 a mixture of chalcones 2 1.
Synthesis, fungicidal and insecticidal activities of. Pyrazoline definition of pyrazoline by the free dictionary. The reaction of halovinylacetylenes and haloallenes with hydrazine and phenylhydrazine in the presence of a mixture of copper powder and cuprous. The results of the in vitro assay against a nonsmall cell lung. Department of chemistry, ugm, sekip utara, yogyakarta, indonesia. Entry ar1 ar2 melting point c yield % found reported3840. Some substituted 3,5diphenyl2pyrazoline1carboxamide derivatives were synthesized from appropriate substituted 1,3diphenylprop2en1one chalcone. Knorr pyrazole synthesis the knorr pyrazole synthesis is an organic reaction used to convert a hydrazine or its derivatives and a 1,3dicarbonyl compound to a pyrazole using an acid catalyst. Their uvvis absorption and fluorescence emission spectra were investigated. As a result, a large number of pyrazoline containing compounds have been developed, and some products have gained application on the clinical level such as azolid tandearil anti inflammatory, phenazone amidopyrene. Synthesis and spectral characterization of novel 2.
Introduction tuberculosis tb, an infection caused by mycobacterium tuberculosis, remains a major global health problem in the. S4 1en3one e1 and 4trifluoromethylphenylhydrazine hydrochloride according to the general procedure for pyrazoline synthesis. Synthesis and antimicrobial activities of various pyrazolines. Synthesis and spectral characterization of novel 2pyrazoline and bis2pyrazoline containing quinoline moiety abstract fulltext html xml download as pdf size. The chalcones 24 were prepared as starting material to obtain the desired pyrazoline and pyrazole derivatives. Udupi, himabindu 1, ajjanna m sridharav 3 1 department of chemistry, jawaharlal nehru technological university kukatpally, hyderabad. Hypervalent iodinemediated rittertype amidation of. An efficient synthetic method has been established for the synthesis of new 3pyrazoline derivative. The synthesis of pyrazole derivatives based on glucose. Novel 2pyrazoline derivatives as potential antibacterial. Pdf in the present study the synthesis of pyrazoline derivatives were carried out by cyclization of the chalcone with hydrazine hydrate in the.
In general the synthesis of pyrazolines involves the basecatalyzed aldol condensation of aromatic ketones to give alpha,beta unsaturated ketones also named as chalcones, which undergo a subsequent cyclization reaction with hydrazine and hydrazine derivatives affording 2 pyrazoline and 2 pyrazoline derivatives. The two nitrogen atoms are adjacent and as we saw for imidazole one of them is a pyrrolelike nitrogen while the other is a pyridinelike nitrogen. S3 1 experimental procedures and analytical data 43tertbutyl14fluorophenyl4,5dihydro1hpyrazol5ylphenol 1b. Chapteriii synthesis and anticancer activity of noval. Pyrazolines are even more special due to their marked physiological and pharmacological activity and distinct functions. Synthesis, antitubercular and analgesic activity evaluation of new 3 pyrazoline derivatives. Methods for the synthesis of substituted hydrazones. This practical and ecofriendly onepot protocol provides a facile access to various di, tri, and tetrasubstituted aryl, alkyl, andor vinyl pyrazoles from readily available. Synthesis and spectral characterization of novel 2 pyrazoline and bis2 pyrazoline containing quinoline moiety. An improved synthesis of 1,3,5triaryl2pyrazolines in. There are elaborate pathways for green and ecofriendly synthesis of pyrazoline derivatives including microwave irradiation, ultrasonic irradiation, grinding and use of ionic liquids which assures the synthesis of the same within much lesser time and by use of minimal energy. Kui du, yijia mei, xianting cao, pengfei zhang, and hui zheng.