- Synthesis of Pyridine Clubbed 2,5-Disubstituted-1,3,4-Oxadiazole Derivatives Shows Potent Antimicrobial Activity
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In the present study, a series of 2,5-disubstituted-1,3,4 oxadiazole analogues retaining pyridine moiety were synthesized (4a-j) by reacting various substituted aromatic acids and isonicotinohydrazide by using POCl3 as a cycling agent. The structure elucidation of all the synthesized compounds was done by chromatographic data and spectral data analysis. The synthesized compounds were evaluated for their in-vitro antimicrobial activity against various strains of ESKAPE pathogens. Antibacterial activity was performed against Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa, while antifungal activity was assayed against Candida albicans and Aspergillus spp. The result of in-vitro antimicrobial studies of all the synthesized compounds revealed that compound 4d and 4f exhibited promising activity against selected microbial strains equally compared to Cefixime and Econazole used as reference drugs.
- Katiyar, Pratima,Singh, Manjul Pratap
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p. 822 - 829
(2022/03/01)
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- The preparation, characterization and catalytic activity of Ni NPs supported on porous alginate-g-poly(p-styrene sulfonamide-co-acrylamide)
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Herein, we report the synthesis of nickel nanoparticles under mild conditions using porous alginate-g-poly(p-styrene sulfonamide-co-acrylamide) as a protecting/stabilizing agent and sodium borohydride as a reducing agent. The porous cross-linked polymeric support was preparedviacombining the use of sol-gel, nanocasting, and crosslinking techniques, in which thep-styrene sulfonamide monomer (PSSA) andN,N′-methylene-bis (acrylamide) (MBA) cross-linker underwent copolymerization on the surface of sodium alginate in the presence of a SiO2nanoparticle (NP) template (Alg-PSSA-co-ACA). The prepared catalyst (Alg-PSSA-co-ACA@Ni) showed high catalytic activity for the one-step synthesis of 1,3,4-oxadiazoles from the reaction of hydrazides and aryl iodides through isocyanide insertion/cyclization.
- Alavinia, Sedigheh,Ghorbani-Vaghei, Ramin
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p. 29728 - 29740
(2021/10/06)
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- Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides
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An oxidative sp3 C–H bond of methyl-azaheteroarenes protocol was reported for the synthesis of 1,3,4-oxadiazoles via [4 + 1] annulation with hydrazides. This protocol enables 1,3,4-oxadiazole and quinoline linked diheterocycles via selective oxidation of sp3 C–H bond of methyl-azaheteroarenes in the presence of I2-DMSO. The reaction has a broad substrate scope and good functional group tolerance for methyl-azaheteroarenes and hydrazides.
- Shang, Zhi-Hao,Sun, Ji-Na,Guo, Jiang-Shan,Sun, Yuan-Yuan,Weng, Wei-Zhao,Zhang, Zhen-Xiao,Li, Zeng-Jing,Zhu, Yan-Ping
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- Electrochemical Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from α-Keto Acids and Acylhydrazines Under Mild Conditions
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1,3,4-Oxadiazoles are a kind of useful heterocycles which can be frequently found in materials and bioactive molecules. In this study, intermolecular electrochemical cyclization between α-keto acids and acylhydrazines has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles with the yield up to 91 %. This transformation can be run under mild reaction conditions in the absence of external oxidant, base and transition metal catalyst. Both symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles could be prepared according to the careful choice of the substrate combination. Gram scale synthesis also illustrates the potential application of this protocol in large preparation.
- Lu, Fangling,Gong, Fengping,Li, Liangsen,Zhang, Kan,Li, Zhen,Zhang, Xinwei,Yin, Ying,Wang, Ying,Gao, Ziwei,Zhang, Heng,Lei, Aiwen
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supporting information
p. 3257 - 3260
(2020/05/25)
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- Convenient entry to N-pyridinylureas with pharmaceutically privileged oxadiazole substituents via the acid-catalyzed C[sbnd]H activation of N-oxides
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Pyridine-N-oxides bearing a pharmacophoric oxadiazole moiety could be C[sbnd]H functionalized via the acid-catalyzed reaction with dialkylcyanamides, providing access to hitherto undescribed pyridine-2-yl substituted ureas, which have potential as “lead-l
- Geyl, Kirill,Baykov, Sergey,Tarasenko, Marina,Zelenkov, Lev E.,Matveevskaya, Vladislava,Boyarskiy, Vadim P.
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supporting information
(2019/09/12)
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- Iodine-promoted one-pot synthesis of 1,3,4-oxadiazole scaffolds: Via sp3 C-H functionalization of azaarenes
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An efficient iodine-mediated one-pot synthetic protocol for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole scaffolds has been developed via sp3 C-H functionalization. Gratifyingly, this method involves oxidative amination with concomitant base-mediated cyclization of methylhetarenes and acylhydrazines by employing iodine and Cs2CO3. The key features of the present method include good functional group tolerance, a clean protocol, metal-free conditions and high yields, making this protocol an attractive strategy towards the synthesis of bioactive molecules and their key building blocks.
- Mani, Geeta Sai,Donthiboina, Kavitha,Shankaraiah, Nagula,Kamal, Ahmed
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p. 15999 - 16006
(2019/10/28)
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- Harnessing Autoxidation of Aldehydes: In Situ Iodoarene Catalyzed Synthesis of Substituted 1,3,4-Oxadiazole, in the Presence of Molecular Oxygen
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Isobutyraldehyde underwent auto-oxidation in the presence of molecular oxygen to generate an acyloxy radical under a "metal-free" environment. They were subsequently exploited in situ to afford hypervalent iodines with p-anisolyl iodide which generated substituted 1,3,4-oxadiazoles in moderate to excellent yields from N′-arylidene acetohydrazides. The reaction strategy tolerated diverse substitution on the hydrazide substrates. Control experiments and literature precedence supported the formation of an in situ iodosylarene complex that facilitates the formation of products.
- Chauhan, Jyoti,Ravva, Mahesh K,Sen, Subhabrata
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p. 6562 - 6565
(2019/09/04)
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- Synthesis of 2,5-disubstituted 1,3,4-oxadiazoles by visible-light-mediated decarboxylation–cyclization of hydrazides and diketones
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A visible-light-induced synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from simple diketones and hydrazides with the assistant of the photocatalyst eosin Y catalyzed decarboxylation and cyclization under mild conditions has been discovered. The reaction tolerates a wide range of functional groups and gives a variety of valuable 1,3,4-oxadiazoles in moderate to good yields. Finally, a plausible reaction mechanism was proposed.
- Diao, Pinhui,Ge, Yanqin,zhang, Wenpei,Xu, Chen,Zhang, Nannan,Guo, Cheng
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supporting information
p. 767 - 770
(2018/02/07)
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- Visible-light-promoted aerobic oxidative cyclization to access 1,3,4-oxadiazoles from aldehydes and acylhydrazides
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A novel and practical access to symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles directly from aldehydes and acylhydrazides using visible light irradiation under an air atmosphere in the presence of eosin Y as an organophotoredox catalyst at rt is reported. This is the first example of oxidative cyclization of acylhydrazones employing air and visible light as inexpensive, readily available, non-toxic, and sustainable reagents.
- Yadav, Arvind K.,Yadav, Lal Dhar S.
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supporting information
p. 2065 - 2069
(2014/04/03)
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- Use of ester formylhydrazones for the synthesis of 1,2,4-triazole and 1,3,4-oxadiazole derivatives
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A series of ester formylhydrazones were synthesised by the reaction of alkyl imidate hydrochlorides with ormylhydrazine. Treatment of the ester formylhydrazones with acetic acid hydrazide, isonicotinic acid hydrazide, nicotinicacid hydrazide, and 4-hydroxybenzhydrazide resulted in the formation of either 4-acylamino-4H-1,2,4-triazoles or 2,5-disubstituted 1,3,4-oxadiazoles. 3-Alkyl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones were synthesised by the reaction of the ester formylhydrazones with carbohydrazide. Some arylidenamino compounds were synthesized by the reaction of 4-amino-4,5-dihydro-1H-1,2,4- triazol-5-ones with several aldehydes. These compounds were characterised by elemental analyses, IR, 1H NMR, and UV spectral techniques.
- Yildirim, Nuri,Bekircan, Olcay
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p. 160 - 163
(2013/07/05)
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- Efficient oxidative cyclisation of acid hydrazides to 2,5-disubstituted 1,3,4-oxadiazoles catalysed by Bu4NI with t-BuOOH as oxidant
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Acid hydrazides or araldehyde N-acylhydrazones can be converted in good yields to, respectively, symmetrical or unsymmetrical, 2,5-disubstituted 1,3,4-oxadiazoles at 60 °C by a Bu4NI-catalysed procedure which requires the presence of a base and 2.5 equiv. of t-butyl hydroperoxide.
- Gao, Peng,Wei, Yunyang
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p. 506 - 510
(2013/09/12)
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- One-pot, three component synthesis of 2,5-disubstituted 1,3,4-oxadiazoles catalyzed by heteropolyacid
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H6[PMo9V3O40] was used as an efficient catalyst for the preparation of 1-aroyl-2-arylidene hydrazines. 2,5-Disubstituted 1,3,4-oxadiazoles have been synthesized by oxidation of 1-aroyl-2-arylidene hydrazines with CrO3 in excellent yields.
- Heravi, Majid M.,Zadsirjan, Vahideh,Bakhtiari, Khadijeh,Bamoharram, Fatemeh F.
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p. 259 - 263
(2013/03/29)
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- Synthesis and biological screening of Some 1,3,4-oxadiazoles
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Treatment of Schiff bases with yellow mercuric oxide and iodine in DMF medium yields the title compounds 1,3,4-oxadiazoles (4a-j). The structures of the newly synthesized compounds were assigned on the basis of IR, 1H NMR, Mass spectral data and elemental analysis. All the new compounds were evaluated for their in vitro antibacterial and antifungal activity. Some of the new compounds showed good activity against some bacteria when compared with the standard drug.
- Ishwar Bhat,Revanasiddappa,Prems, Jisha,Mumtaz Mohammed Hussain
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p. 183 - 184
(2013/09/24)
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- Synthesis and in vitro antimicrobial evaluation of condensed heterocyclic 6-substituted 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole and 1,3,4-oxadiazole derivatives of isoniazid
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A series of 6-substituted-1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole (3a-g) and 1,3,4-oxadiazole (4a-g, 5) derivatives of isoniazid were synthesized in satisfactory yield and pharmacologically evaluated for their in vitro antimicrobial activity. All the synthesized compounds were in good agreement with elemental and spectral data. A majority of the tested compounds showed good to moderate antimicrobial activity against all tested pathogenic bacterial and fungal strains.
- Gilani, Sadaf Jamal,Khan, Suroor Ahmad,Alam, Ozair,Siddiqui, Nadeem
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experimental part
p. 205 - 211
(2011/10/09)
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- N-chlorosuccinimide/1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-mediated synthesis of 2,5-disubstituted 1,3,4-oxadiazoles
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A mixture of N-chlorosuccinimide and 1,8-diazabicyclo[5.4.0]undec-7-ene oxidatively cyclizes structurally diverse acyl hydrazone, thereby providing an efficient and convenient method for the synthesis of various 2,5-disubstituted 1,3,4-oxadiazoles. The salient features of this method are mild reaction conditions, short reaction time, excellent yields, and simple workup procedure. Copyright
- Pardeshi, Santosh P.,Patil, Sachin S.,Bobade, Vivek D.
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experimental part
p. 1601 - 1606
(2010/06/20)
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- Synthesis and pharmacological evaluation of condensed heterocyclic 6-substituted 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole and 1,3,4-oxadiazole derivatives of isoniazid
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The significance of this study was to prepare various isoniazid derivatives by introducing the isoniazid core into several molecules to explore the possibilities of some altered biological activities. Series of 6-substituted-1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole (3a-g) and 1,3,4-oxadiazole (4a-g and 5) derivatives of isoniazid were synthesized in satisfactory yield and pharmacologically evaluated for their anti-inflammatory, analgesic, ulcerogenic, and lipid peroxidation activities by known experimental models.
- Gilani, Sadaf J.,Khan, Suroor A.,Siddiqui, Nadeem
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experimental part
p. 4762 - 4765
(2010/10/04)
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- Convenient preparation of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles promoted by Dess-Martin reagent
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2,5-Disubstituted 1,3,4-oxadiazoles have been conveniently prepared by oxidative cyclization of N-acyl-N′-aryliden-hydrazines promoted by an excess of Dess-Martin periodinane under mild conditions (23 examples, up to 92% isolated yields).
- Dobrotǎ, Cristian,Paraschivescu, Codru?a C.,Dumitru, Ioana,Matache, Mihaela,Baciu, Ion,Ru?ǎ, Lavinia L.
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scheme or table
p. 1886 - 1888
(2009/07/05)
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- Synthesis of substituted N-[4(5-Methyl/phenyl-1,3,4-oxadiazol-2- Yl)-3,6-dihydropyridin-1(2H)-yl]benzamide/benzene sulfonamides as anti-inflammatory and anti-cancer agents
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Fourteen novel substituted N-[4(5-methyl/phenyl-1,3,4-oxadiazol-2-yl)-3,6- dihydropyridin-1(2H)-yl] benzamide/benzene sulfonamides (11a-n) were synthesized in fair to good yields via sodium borohy-dride reduction of the corresponding substituted N-(benzoylimino)-4-(5-methyl/5-phenyl-1,3,4-oxadia- zol-2yl) pyridinium ylide (10a-n) in absolute ethanol.
- Gangapuram, Madhavi,Redda, Kinfe K.
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experimental part
p. 309 - 316
(2009/07/19)
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- Greener and rapid access to bio-active heterocycles: one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles
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A novel one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles by condensation of acid hydrazide and triethyl orthoalkanates under microwave irradiations is reported. This green protocol was catalyzed efficiently by solid supported NafionNR50 and phosphorus pentasulfide in alumina (P4S10/Al2O3) with excellent yields.
- Polshettiwar, Vivek,Varma, Rajender S.
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p. 879 - 883
(2008/09/17)
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- Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines
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4-(5-Substituted-1,3,4-oxadiazol-2-yl)pyridine derivatives 1-12 were synthesized and evaluated for their in vitro antimycobacterial activity. Some compounds showed an interesting activity against Mycobacterium tuberculosis H37Rv and five clinic
- Navarrete-Vazquez, Gabriel,Molina-Salinas, Gloria Maria,Duarte-Fajardo, Zetel Vahi,Vargas-Villarreal, Javier,Estrada-Soto, Samuel,Gonzalez-Salazar, Francisco,Hernandez-Nunez, Emanuel,Said-Fernandez, Salvador
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p. 5502 - 5508
(2008/03/14)
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- Silica sulfuric acid: An efficient and versatile acidic catalyst for the rapid and ecofriendly synthesis of 1,3,4-oxadiazoles at ambient temperature
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A rapid and green synthesis of 2,5-disubstituted 1,3,4-oxadiazoles is reported. The title compounds were prepared by the reaction of different acyl hydrazides and orthoesters in the presence of silica sulfuric acid under solvent-free conditions. In this new process, reactions were run at ambient temperature and completed in a short period of time with high yields. Copyright Taylor & Francis Group, LLC.
- Dabiri, Minoo,Salehi, Peyman,Baghbanzadeh, Mostafa,Zolfigol, Mohammad Ali,Bahramnejad, Mahboobeh
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p. 1201 - 1209
(2008/02/01)
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- Synthesis and characterization of 1,3,4-oxadiazole-triazolopyridinone hybrid derivatives as new blue-greenish photoluminescent materials
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(Chemical Equation Presented) Recently, New functionalized oxadiazole-triazolopyridinone hybrid compounds were investigated as photoluminescent materials. In this work, we introduce triazolopyridinone to synthesize a series of oxadiazole-triazolopyridinon
- Chiang, Kuo-Chen,Fung, Fuh Wong,Chang, Chih-Shiang,Hour, Mann-Jen,Wang, Yu-Ling,Wen, Shaw-Bing,Yeh, Mou-Yung
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p. 591 - 596
(2008/09/18)
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- A facile procedure for the one-pot synthesis of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles
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Unsymmetrically 2,5-disubstituted 1,3,4-oxadiazoles were efficiently synthesized from the cyclization-oxidation reaction of acyl hydrazones. Also, the synthesis of the title compounds was achieved by the condensation of acyl hydrazides and aromatic aldehydes in the presence of ceric ammonium nitrate in dichloromethane.
- Dabiri, Minoo,Salehi, Peyman,Baghbanzadeh, Mostafa,Bahramnejad, Mahboobeh
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p. 6983 - 6986
(2007/10/03)
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- Iodobenzene diacetate mediated solid-state synthesis of heterocyclyl-1,3,4-oxadiazoles
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A simple and efficient method has been developed for the oxidation of various heterocyclyl acylhydrazones 3 with iodobenzene diacetate (IBD) to heterocyclyl-1,3,4-oxadiazoles 4 in solid state. The reaction took place at room temperature within few minutes. The products were isolated by simple aqueous work-up in good yields.
- Rao,Chandra Sekhar
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p. 2153 - 2157
(2007/10/03)
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- An expeditious and convenient one pot synthesis of 2,5-disubstituted-1,3,4-oxadiazoles
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A convenient, one pot procedure is reported for the synthesis of a variety of 2,5-disubstituted-1,3,4-oxadiazoles by condensing monoarylhydrazides with acid chlorides in HMPA solvent under the microwave heating. The yields are good to excellent, the process is rapid and does not need any added acid catalyst or dehydrating reagent.
- Mashraqui, Sabir H.,Ghadigaonkar, Shailesh G.,Kenny, Rajesh S.
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p. 2541 - 2545
(2007/10/03)
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- SYNTHESIS OF 2,5-DISUBSTITUTED 1,3,4-OXADIAZOLES FROM TRICHLOROMETHYLARENES AND ACYLHYDRAZINES
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A preparative synthesis of 2,5-disubtituted 1,3,4-oxadiazoles by the reaction of trichloromethylarenes with hydrazides of carboxylic acids of the aliphatic, aromatic and heteroaromatic series in methanol or ethanol in the presence of pyridine was developed.
- Poddubnyi, I. S.,Belen'skii, L. I.,Krayushkin, M. M.
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p. 602 - 607
(2007/10/02)
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- TETRAZOLES IN THE SYNTHESES OF 1,3,4-OXADIAZOLES
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Various variants of cleavage of tetrazoles to form 1,3,4-oxadiazoles are examined.The mechanisms and synthetic potentialities of these reactions are discussed.
- Koldobskii, G. I.,Ivanova, S. E.
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p. 1512 - 1517
(2007/10/03)
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- Studies on Thioamides and Their Derivatives,VI. New Synthesis of 5-Membered Heterocyclic Compounds
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Simple N-monosubstituted thioamides react with acid hydrazides to form 1,2,4-triazole derivatives.N,N-Disubstituted thioamides alkylated with methyl iodide readily yield with acid hydrazides 1,3,4-oxadiazoles.
- Santus, Maria
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p. 179 - 182
(2007/10/02)
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- Oxydations d'hydrazones par le bioxyde de plomb: nouvelles syntheses d'oxadiazoles-1,3,4 et de derives de l'amino-4 triazol-1,2,4 one-5
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Aromatic aldehyde aroylhydrazones when oxidized with lead dioxide, in acetic acid, gave quickly the corresponding 1,3,4-oxadiazoles in good yields.Aromatic aldehyde carbodihydrazones on the other hand, gave derivatives of 4-amino-3-aryl-1,2,4-triazol-5-ones, in dimethylformamide as solvent.To explain these results, some radical mechanisms are proposed.
- Milcent, Rene,Barbier, Geo
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