scholarly journals Ferric Hydrogensulfate As a Reusable Heterogeneous Catalyst for the Synthesis of 5-Substituted-1H-Tetrazoles and Amides

2011 ◽  
Vol 2011 ◽  
pp. 1-5 ◽  
Author(s):  
Hossein Eshghi ◽  
Seyed Mohammad Seyedi ◽  
Elaheh Rahimi Zarei

Ferric hydrogensulfate catalyzed the synthesis of 5-substituted 1H-tetrazoles via [2 + 3] cycloaddition of nitriles and sodium azide. This method has the advantages of high yields, simple methodology, and easy workup. The catalyst can be recovered by simple filtration and reused delivering good yields. Also, ferric hydrogensulfate catalyzed the hydrolysis of nitriles to primary amides under aqueous conditions. Various aliphatic and aromatic nitriles converted to the corresponding amides in good yields without any contamination with carboxylic acids.

RSC Advances ◽  
2015 ◽  
Vol 5 (62) ◽  
pp. 49849-49860 ◽  
Author(s):  
Sara S. E. Ghodsinia ◽  
Batool Akhlaghinia

A convenient, rapid and metal free synthesis of 5-substituted-1H-tetrazoles by [3 + 2] cycloaddition reaction of nitriles with sodium azide. Cuttlebone as a natural low cost heterogeneous catalyst affords 5-substituted-1H-tetrazoles rapidly with high efficiency.


2003 ◽  
Vol 2003 (3) ◽  
pp. 174-175 ◽  
Author(s):  
V.B. Helavi ◽  
S.B. Solabannavar ◽  
U.V. Desai ◽  
R.B. Mane

Microwave induced hydrolysis of alkyl Medrum's acids and decarboxylation of derived malonic acids using poly-4-vinylpyridine as a catalyst gives high yields of carboxylic acids in a short time.


2005 ◽  
Vol 2005 (2) ◽  
pp. 119-120 ◽  
Author(s):  
Majid M. Heravi ◽  
Dordaneh Zargarani ◽  
Rahim Hekmat Shoar ◽  
Shahnaz Khaleghi

Amides efficiently and rapidly give carboxylic acids in high yields upon reaction with phthalic anhydride under microwave irradiation in the absence of solvent.


1984 ◽  
Vol 49 (11) ◽  
pp. 2509-2519 ◽  
Author(s):  
Ctibor Mazal ◽  
Zdeněk Jurka ◽  
Jaroslav Jonas

(E) and (Z)-3-(4-toluenesulfonyloxymethylene)dihydro-2(3H)-furanones ((E)-I) and ((Z-I) react with piperidine, pyrrolidine, morpholine, butanethiol, 4-toluenethiol, and 2-naphthalenethiol to give (E)-isomers of the corresponding enamines II-IV and thiomethylene derivatives V-VII in high yields. As has been shown, the reactions proceed with retention of configuration; the initially formed (Z)-II, (Z)-III, (Z)-IV, and (Z)-V isomerize rapidly to the thermodynamicaly more stable (E)-isomers. Ether IX was obtained by reaction of (E)-I with the (E)-isomer of sodium salt of 3-(hydroxymethylene)dihydro-2(3H)-furanone ((E)-VIII) and a mixture of ethers IX and X resulted from reaction of (Z)-I with sodium salt of (E)-VIII. Compounds (E)-I and (Z)-I afforded the corresponding azides(E)-XI and (Z)-XI upon treatment with sodium azide, and hydroxybutanoic acids (E)-XII and (Z)-XII with sodium hydroxide in aqueous acetone. Chloride (E)-XIII, prepared by reacting (E)-I with methanolic hydrogen chloride, furnished with piperdine, pyrrolidine, morpholine, or 2-naphthalenethiol the corresponding (E)-II, (E)-III, (E)-IV, and (E)-VII. Potassium cyanide reacted with (E)-I in dimethylsulfoxide to yield nitrile (E)-XIV. Cycloaddition of the azide (E)-XI to isobutyl vinyl ether or cyclohexyl vinyl ether proceeds quantitatively to give the respective triazolines (E)-XV and (E)-XVI. Alkaline hydrolysis of IX afforded the acid XVII. reduction of (E)-I, (Z)-I, and (E)-VII with chloralane gave the respective butanediols (E)-XVIII, (Z)-XVIII, and (E)-XIX, respectively. Configurations of these substances were elucidated by 1H NMR spectrometry.


1999 ◽  
Vol 45 (10) ◽  
pp. 811-815 ◽  
Author(s):  
Jasvinder Dhillon ◽  
Suneel Chhatre ◽  
Rishi Shanker ◽  
N Shivaraman

A Pseudomonas sp. (S1) isolated from a garden soil possessed a unique nitrilase, which is capable of catalyzing the direct hydrolysis of both potassium and organic cyanides to their corresponding carboxylic acids and ammonia, without the formation of amide as an intermediate. The nitrilase was purified with 4.8% recovery in three steps from a cell extract of the strain. The relative mobility of the homogenous enzyme preparation in SDS and native polyacrylamide gels indicated molecular weight of 41 kDa, approximately. Pseudomonas sp. (S1) utilized all the nitriles as carbon and nitrogen sources. The enzyme was induced by both aliphatic and aromatic nitriles, while the aliphatic olefinic nitrile - acrylonitrile was the most suitable substrate. The nitrilase also catalyzed the hydrolysis of acetonitrile, adiponitrile, benzonitrile, butyronitrile, glutaronitrile, phenylacetonitrile, succinodinitrile, and potassium cyanide, with the formation of ammonia and the corresponding carboxylic acids. The Michaelis-Menten constant, Km, of the partially purified nitrilase for acetonitrile, acrylonitrile, adiponitrile, benzonitrile, and potassium cyanide presented values of 11.26, 5.88, 10.28, 12.27, and 0.75 mM, respectively.Key words: nitriles, enzyme kinetics, nitrilase, partial purification, Pseudomonas sp.


2018 ◽  
Vol 21 (4) ◽  
pp. 298-301 ◽  
Author(s):  
Ghasem Marandi

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.


1975 ◽  
Vol 28 (3) ◽  
pp. 673 ◽  
Author(s):  
DJ Collins ◽  
C Lewis ◽  
JM Swan

Treatment of cyclododecane-r-1,c-5,c-9-triyl tris(p-toluenesulphonate) with sodium azide in dimethyl-formamide at 100� for 6 h gave the corresponding cis,cis-triazide which upon hydrogenation or reduction with lithium aluminium hydride gave cyclododecane-r-1,c-5,c-9-triamine, isolated as the tris-salicylidene derivative. Acid hydrolysis of this, removal of the salicylaldehyde, and treatment of the aqueous solution with sodium carbonate and 2,3-dimethoxybenzoyl chloride gave r-1,c-5,c- 9-tris(2,3-dimethoxybenzamido)cyclododecane. ��� Treatment of (E,E,E)-cyclododeca-1,5,9-triene with an excess of acetonitrile and sulphuric acid at room temperature for three days gave 18% of (E,E)-1-acetamidocyclododeca-4,8-diene; no di- or tri-amides were isolated.


Author(s):  
Udayakumar Veerabagu ◽  
Gowsika Jaikumar ◽  
Fushen Lu ◽  
Franck Quero

The 3 wt% CuI/BNNS catalyst exhibited high efficiency for C–H difluoromethylation reactions and enabled greener synthesis at high yields using cyrene as a solvent. Furthermore, the catalyst could be easily recovered and recycled for at least five cycles.


2017 ◽  
Vol 23 (5) ◽  
Author(s):  
Kerru Nagaraju ◽  
Gummidi Lalitha ◽  
Parvesh Singh ◽  
Chunduri Venkata Rao

AbstractReaction between substituted thiazolylamine or oxazolylamine, triethyl orthoformate and sodium azide in the presence of tributylmethylammonium chloride in DMSO furnishes 1-substituted 1


1992 ◽  
Vol 271 ◽  
Author(s):  
Charles D. Gagliardi ◽  
Dilum Dunuwila ◽  
Beatrice A. Van Vlierberge-Torgerson ◽  
Kris A. Berglund

ABSTRACTTitanium alkoxides modified by carboxylic acids have been widely studied as the molecular precursors to ceramic materials. These alkoxide complexes have also been very useful in the formation of stable, porous, optically clear films having many novel applications such as chemical sensors, catalytic supports, and ion-exchange media. To improve the processing of these materials, it is essential to better understand the kinetics of the chemical transformations which occur.The kinetics of the hydrolysis reaction are studied for selected carboxylic acids using Raman spectroscopy to probe the chemistry of the process. The study has a special emphasis on the titanium isopropoxide-valeric acid system due to the superior quality of these films over other carboxylates. Greater knowledge of the hydrolysis kinetics allows increased control over the quality of the film materials and should be of general interest to those working with modified metal alkoxides.


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