Design, synthesis and biological evaluation of some novel. Based on the neuroprotective properties of 2pyrazoline derivatives, in the current work. The sequence leading to the title compounds is outlined in scheme 1. S3 1 experimental procedures and analytical data 43tertbutyl14fluorophenyl4,5dihydro1hpyrazol5ylphenol 1b. Pdf synthesis and anticonvulsant activity of some substituted 3,5. Synthesis, antibacterial and antifungal activity of some new. Nmr results suggests that only the rc snh 2 and rc onh 2 species, more stable, are present.
Then, addition of hydrazine hydrate afforded pyrazoline intermediates. Synthesis and spectral characterization of novel 2. Novel 2pyrazoline derivatives as potential antibacterial. Synthesis and antimicrobial activities of various pyrazolines. After the formation of the cycloadduct 11, an imine to enamine tautomerization occurs to form the enamine tautomer 12. Wadhwani college of pharmacy, yavatmal, maharashtra, india corres. There are various green techniques available in the literature for synthesis of pyrazoline derivatives. Synthesis of pyrazoline derivative was performed in a manner as outlined in scheme 2 and 3. Chapteriii synthesis and anticancer activity of noval. Cecl3 7h2o catalysed synthesis of 2pyrazoline derivatives 1443 1 2 3 510 c scheme 1.
Entry ar1 ar2 melting point c yield % found reported3840. Synthesis of pyrazoline derivatives from halovinylacetylenes. Pyrazoline synonyms, pyrazoline pronunciation, pyrazoline translation, english dictionary definition of pyrazoline. Synthesis of nheterocycles synthesis of pyrazolines. It forms white crystals or white crystalline powder. Pdf synthesis and characterization of pyrazoline derivatives. The title compound was prepared by reaction of e14tertbutoxyphenyl4,4dimethylpent1en3one e1 and 4fluorophenylhydrazine hydrochloride according to the general procedure for pyrazoline synthesis. Xiaoyong duan, xiulong yang, panpan jia, man zhang, bing han. 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. Synthesis, antimicrobial and antitubercular activities of. The synthesized cycloadduct displayed a tendency to exhibit an imineenamine type of. The results of the in vitro assay against a nonsmall cell lung. Their experiment seems to be the first example of pyrazoline formation by the reaction of an. 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.
The synthesis of pyrazole derivatives based on glucose. Apr 02, 2014 an experimental study on the synthesis, tautomerism and acid promoted structural changes of spiropyrazolines is described. 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. A strategy for the synthesis of pyrazolinefunctionalized oxindoles. 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. The compound of different pyrazoline derivatives were synthesized by cyclisation of substituted chalcone derivatives in the presence of 2, 4 dintro phenyl. In order to quickly refresh your memory, a pyrrolelike nitrogen is a nonbasic nitrogen, with a lone pair involved. The 1 h nmr spectra of the compounds showed three doublet of doublets in the regions of. The chalcones 24 were prepared as starting material to obtain the desired pyrazoline and pyrazole derivatives.
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. Synthesis and pharmacological activities of pyrazole. Feprazone also finds use in the treatment of rheumatic disorders. Pdf synthesis and characterization of a novel 2pyrazoline. 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. 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. Kshirsagar2, sarita singhal1 1mahatma jyoti rao phoole university, jaipur, rajasthan, india 2p. Synthesis and spectral characterization of novel 2 pyrazoline and bis2 pyrazoline containing quinoline moiety. An efficient synthetic method has been established for the synthesis of new 3pyrazoline derivative. Ethyl 1,2,4 triazolo3,4c1,2,4triazino5,6b5hindole5ethanoate 26 and 15h. A proposed mechanism for formation of the pyrazole via spiropyrazoline ring opening is shown in scheme 3. General procedure for the synthesis of pyrazolines 4 a mixture of chalcones 2 1. We have recently explored the synthesis and antimicrobial activity of a series of compounds having aryloxy substituents attached to pyrazoline. The compound has been fully characterized by 1h, c nmr.
Their uvvis absorption and fluorescence emission spectra were investigated. 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. Pdf the chemistry of chalcones has generated intensive scientific studies throughout the world. An efficient synthesis of some new chalcone, acetyl. Synthesis and fluorescent property of pyrazoline derivatives. 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. Synthesis, antitubercular and analgesic activity evaluation of new 3 pyrazoline derivatives. Since conventional methods of organic synthesis are energy. Introduction tuberculosis tb, an infection caused by mycobacterium tuberculosis, remains a major global health problem in the. 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, antibacterial and antifungal activity of some. 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. Some substituted 3,5diphenyl2pyrazoline1carboxamide derivatives were synthesized from appropriate substituted 1,3diphenylprop2en1one chalcone. S4 1en3one e1 and 4trifluoromethylphenylhydrazine hydrochloride according to the general procedure for pyrazoline synthesis.
Synthesis, spectroscopic and computational characterization. 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. The reaction of halovinylacetylenes and haloallenes with hydrazine and phenylhydrazine in the presence of a mixture of copper powder and cuprous. Udupi, himabindu 1, ajjanna m sridharav 3 1 department of chemistry, jawaharlal nehru technological university kukatpally, hyderabad 500072.
Pyrazoline is a heterocyclic chemical compound with the molecular formula c 3 h 6 n 2. Synthesis, antimicrobial and antiinflammatory studies of. Ecofriendly synthesis of pyrazoline derivatives impact factor. 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.
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. Highlights a series of novel diphenyl sulfonebased bispyrazoline derivatives were designed and synthesized. An i 2mediated metalfree oxidative cn bond formation enables a regioselective pyrazole synthesis. 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 biological activities exhibited by the pyrazoline compounds, revanasiddappa32 et al. Pyrazolines are even more special due to their marked physiological and pharmacological activity and distinct functions. An ironcatalyzed route for the regioselective synthesis of 1,3 and 1,3,5substituted. Synthesis, anticancer activity, and docking study of nacetyl. Bhandari, synthesis, antimicrobial and antitubercular activities of some novel pyrazoline derivatives, journal of saudi chemical society, vol. A new series of benzothiazolepyrazoline hybrids 4ap were synthesized from condensation reaction of intermediate chalcones by cyclizing with phenyl hydrazine.
Synthesis, photoluminescence properties and theoretical insights on 1,3diphenyl59anthryl2 pyrazoline and 1hpyrazole. Synthesis and spectral characterization of novel 2pyrazoline and bis2pyrazoline containing quinoline moiety abstract fulltext html xml download as pdf size. Synthesis of 1,3,5trisubstituted2pyrazolines compound p 54fluorophenyl34fluorophenyl1isonicotinoylpyrazoline 9,10 was performed by taking equimolar quantities 0. 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 and spectral characterization of novel 2pyrazoline. This reaction was conducted in formic acid in presence of bf3et2o or in acetic acid. An efficient synthesis of some new chalcone, acetyl pyrazoline and amino pyrimidine bearing 1,3,5triazine nucleus as potential antimicrobial and antitubercular agent. The mechanism begins with an acid catalyzed imine formation, where in the case of hydrazine derivatives the attack can happen on either carbonyl carbon. The desired compounds were prepared by the reaction of 6,6dimethyl4oxo4,5,6,7tetrahydro1hindole2carbaldehyde 1 with different acetophenones. This article about a heterocyclic compound is a stub. 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. It is a pyrazoline derivative which is chemically 2,3dimethyl1phenyl 3pyrazolin5one. Pdf in the present study the synthesis of pyrazoline derivatives were carried out by cyclization of the chalcone with hydrazine hydrate in the. Pyrazoline definition of pyrazoline by the free dictionary.
Chemicals and reagent furan2carbaldehyde, various acetophenone, phenyl hydrazine, hydrazine hydrate, ethanol, ampicillin and griseofulvin. Department of chemistry, ugm, sekip utara, yogyakarta, indonesia. A series of new pyrazoline derivatives containing pyridine, piperazine and amide linkage were prepared through multistep synthesis. The pyrazoline compounds 309 and their 1acetylated derivatives congiu et al. The present study aims at the synthesis of pyrazolines bearing benzothiazole and their evaluation as anticancer agents. The photoinduced electrontransfer thermodynamics of the derivatives was estimated on the basis of the spectroscopic data and redox potentials of. So, pertaining to its importance, many attempts are made to synthesize pyrazolines. Udupi, himabindu 1, ajjanna m sridharav 3 1 department of chemistry, jawaharlal nehru technological university kukatpally, hyderabad. The structures of the newly synthesized compounds were confirmed by ir, 1h nmr, lcms and hplc elemental analysis.
Reaction of substituted acetophenones and benzaldehydes to form chalcones. Synthetic and biological studies of pyrazolines and related. The structures of these compounds were confirmed by. An ecofriendly synthesis of 2pyrazoline derivatives. Taj t, kamble rr,gireesh tm, hunnur rk and margankop sb.
Tuning the photoinduced electrontransfer thermodynamics in 1. 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. Pyrazole is an aromatic heterocyclic compound characterized by a five membered ring with formula c 3 h 3 n 2 h. An experimental study on the synthesis, tautomerism and acid promoted structural changes of spiropyrazolines is described. First, the chalcones were prepared fron substituted aldehydes and ketones in the presence of alkali naoh and alcohol as solvent medium. Synthesis, xray crystal structure and optical properties. New 2pyrazoline derivatives 15 bearing benzenesulfonamide moieties were then synthesized by condensing the appropriate chalcones 24 with 4hydrazinyl benzenesulfonamide hydrochloride. All the compounds were stable in the solid as well as in the solution state. Diversely substituted pyrazolines embedded with a variety of functional groups are found in many important biologicallyactive compounds and.
Synthesis and evaluation of new pyrazoline derivatives as. Kui du, yijia mei, xianting cao, pengfei zhang, and hui zheng. This practical and ecofriendly onepot protocol provides a facile access to various di, tri, and tetrasubstituted aryl, alkyl, andor vinyl pyrazoles from readily available. During the last century, after these pioneering studies, numerous 2pyrazolines. A novel synthesis of 1,3,5trisubstituted pyrazoles. These compounds were prepared by cyclocondensation of chalcones and bischalcones in presence of hydrazine hydrate. The new prepared compounds will contain both quinoline and pyrazoline moieties. The structures of nphenyl pyrazoline derivatives 7a. Synthesis of 3acetyl4hydroxyphenyl acetamide 1 a mixture of pacetamidophenol 0. Instead of compound 12 reverting to 11, the enamine tautomer undergoes an eliminatory ring cleavage of the indoline ring at the spirocyclic carbon. Beiqiong lu, jianming zhang, mingjian wang, yuanhai zhou, xiaolei chen.
Methods for the synthesis of substituted hydrazones. Review on synthesis of bioactive pyrazoline derivatives. 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. Synthesis, antitubercular and analgesic activity evaluation of new 3pyrazoline derivatives. Design, synthesis and biological evaluation of novel antitubercular agents by combining pyrazoline and benzoxazole pharmacophores hemal m. The structures of the compounds 3ag were determined by ir, 1 h nmr and hrms spectral data. Tuning the photoinduced electrontransfer thermodynamics. Synthesis of ethyl 3,5substituteddiphenyl4,5dihydropyrazole1carboxylate derivatives c 1c 6. One pot synthesis of pyrazoline derivatised carbazoles as antitubercular, anticancer agents, their dna cleavage and antioxidant activities. Synthesis of pyrazoline derivatives from halovinylacetylenes and haloallenes. A series of 2pyrazolines 59 have been synthesized from. Remove the stirrer and leave the reaction mixture in an ice chest or. Led by these considerations, it appeared of interest to synthesize novel pyrazoline derivatives and screened for their antimicrobial activities.
Synthesis, antimicrobial and antiinflammatory studies of pyrazoline analogues of rosuvastatin sanath kumar goud palusa 1, 2, rajgopal h. The synthesized cycloadduct displayed a tendency to exhibit an imineenamine. A strategy for the synthesis of pyrazoline functionalized oxindoles. 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. Synthetic and biological studies of pyrazolines and. Synthesis of different chalcones using substituted acetophenones and benzaldehydes. Hypervalent iodinemediated rittertype amidation of. These approaches were extended to bischalcones, which delivered functionalized.
Synthesis, fungicidal and insecticidal activities of. An improved synthesis of 1,3,5triaryl2pyrazolines in. The synthesis of arylsubstituted pyrazolines 73 has been developed by matthias beller and coworkers alex et al. As microwave irradiation facilitates the polarization of the molecule, the. With increasing the solvent polarity, fluorescence emission displayed a redshift and fluorescence quantum yields decreased. Synthesis, antimicrobial and antitubercular activities of some novel. 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. The synthesis of novel pyrazoline derivatives and investigation of their chemical and biological behavior have gained more improved potency and lesser toxicity. A novel synthesis of 1,3,5trisubstituted pyrazoles through a. Synthesis and antimicrobial activities of various pyrazolines from chalcones vishal d. The relationship of substituents and the optical properties were discussed.