scholarly journals Synthesis of 2-(aminophenyl)adenine derivatives: a simple protocol using the classical iron powder/acetic acid reduction methodology

2020 ◽  
Vol 98 (3) ◽  
pp. 145-150
Author(s):  
A. Rocha ◽  
M.F. Proença ◽  
M. Alice Carvalho
Keyword(s):  
Acetic Acid ◽  
Iron Powder ◽  
Functional Groups ◽  
Good Yield ◽  
Aqueous Ethanol ◽  
Simple Protocol ◽  
Simple Filtration ◽  
Nitro Derivatives ◽  
Acid Reduction ◽  
Adenine Derivatives

2-(Nitrophenyl)adenine derivatives were isolated from the reaction of 5-amino-4-amidino-imidazoles with nitrobenzaldehydes. The conversion of the nitro derivatives to 2-(aminophenyl)adenine derivatives was performed using iron/acetic acid as reducing agent, in 70% aqueous ethanol. The products were isolated in good yield and the isolation protocol involves simple filtration and extraction procedures. This methodology is compatible with the presence of functional groups such as amines, ethers, halofluorides, and halochlorides.

Preparation of Some 2-(Methoxyphenyl)-2H-benzotriazoles and the Corresponding Hydroxyphenyl Compounds

1987 ◽  
Vol 40 (10) ◽  
pp. 1663 ◽  
Author(s):  
J Rosevear ◽  
JFK Wilshire
Keyword(s):  
Acetic Acid ◽  
Good Yield ◽  
Hydrobromic Acid ◽  
Methoxy Group ◽  
Methylene Chloride ◽  
Thiourea Dioxide ◽  
Boron Tribromide

The reaction of several substituted o- nitronitrosobenzenes with O- and p- anisidine , and 2,4- dimethoxyaniline in acetic acid gives in good yield the corresponding enitroazobenzenes which are readily reduced with thiourea dioxide ( formamidinesulfinic acid) to the corresponding 2-(methoxypheny1)-2H-benzotriazoles, demethylation of which furnished the corresponding 2- (hydroxypheny1)-2H-benzotriazoles. Demethylation of the dimethoxy derivatives was best accomplished with boron tribromide in methylene chloride, the methoxy group located ortho to the benzotriazole ring being demethylated more readily than is the para-methoxy group. The reaction of enitroazobenzenes containing a methoxy group with hydrobromic acid in acetic acid results in cleavage of the azo bond and also partial bromination to give o- nitroaniline and some of its brominated derivatives.

New Phosphorylating Agents for the Synthesis of Phosphatidylethanolamines

Synthesis ◽  
2021 ◽  
Author(s):  
Kouta Tsubaki ◽  
Tomoki Yamanaka ◽  
Takuya Hisamitsu ◽  
Hirokazu Shimooka ◽  
Mitsuru Kitamura ◽  
...  
Keyword(s):  
Functional Groups ◽  
Good Yield

The preparation of three different new phosphorylating agents and their application toward the synthesis of phosphatidylethanolamines are described. These reagents are stable to air and moisture, and phosphorylate a glycerol in good yield. The experimental procedures involved using these phosphorylating agents are simple. Moreover, the appropriate reagent can be selected based on the desired functional groups of the targeting phosphatidylethanolamine.

Advances in Alkene and Alkyne Metathesis

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Acetic Acid ◽  
Diels Alder ◽  
Alkyne Metathesis ◽  
Santa Barbara ◽  
Ring Closing Metathesis ◽  
Enol Ethers ◽  
Cross Metathesis ◽  
Simple Filtration ◽  
The University ◽  
Academy Of Sciences

As alkene metathesis is extended to more and more challenging substrates, improved catalysts and solvents are required. Robert H. Grubbs of Caltech developed (Organic Lett. 2008, 10, 441) the diisopropyl complex 1, that efficiently formed the trisubstituted alkene 6 by cross metathesis of 4 with 5. Hervé Clavier and Stephen P. Nolan of ICIQ, Tarragona, and Marc Mauduit of ENSC Rennes found (J. Org. Chem. 2008, 73, 4225) that after cyclization of 7 with the complex 2b, simple filtration of the reaction mixture through silica gel delivered the product 8 containing only 5.5 ppm Ru. The merit of CH2Cl2 as a solvent for alkene metathesis is that the catalysts (e.g. 1 - 3) are very stable. Claire S. Adjiman of Imperial College and Paul C. Taylor of the University of Warwick established (Chem. Commun. 2008, 2806) that although the second generation Grubbs catalyst 3 is not as stable in acetic acid, for the cyclization of 9 to 10 it is a much more active catalyst in acetic acid than in CH2Cl2 . Bruce H. Lipshutz of the University of California, Santa Barbara observed (Adv. Synth. Cat . 2008, 350, 953) that even water could serve as the reaction solvent for the challenging cyclization of 11 to 12, so long as the solubility- enhancing amphiphile PTS was included. Ernesto G. Mata of the Universidad Nacional de Rosario explored (J. Org. Chem. 2008, 73, 2024) resin isolation to optimize cross-metathesis, finding that the acrylate 13 worked particularly well. Karol Grela of the Polish Academy of Sciences, Warsaw optimized (Chem. Commun. 2008, 2468) cross-metathesis with a halogenated alkene 16. Jean-Marc Campagne of ENSC Montpellier extended (J. Am. Chem. Soc. 2008, 130, 1562) ring-closing metathesis to enynes such as 19. The product diene 20 was a reactive Diels-Alder dienophile. István E. Markó of the Université Catholique de Louvain applied (Tetrahedron Lett. 2008, 49, 1523) the known (OHL 20070122) ring-closing metathesis of enol ethers to the cyclization of the Tebbe product from 23. The ether 24 was oxidized directly to the lactone 25.

Convergent functional groups. VIII. Flexible model receptors for adenine derivatives

1990 ◽  
Vol 112 (23) ◽  
pp. 8408-8414 ◽  
Author(s):  
Tjama Tjivikua ◽  
Ghislain Deslongchamps ◽  
Julius Rebek
Keyword(s):  
Functional Groups ◽  
Flexible Model ◽  
Adenine Derivatives

Co and Ni catalysts loaded on typical well-ordered micro- and mesoporous supports for acetic acid reduction

2017 ◽  
Vol 121 (1) ◽  
pp. 109-119 ◽  
Author(s):  
György Onyestyák ◽  
Gyula Novodárszki ◽  
Ágnes Farkas Wellisch ◽  
Dénes Kalló ◽  
Ashim J. Thakur ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Ni Catalysts ◽  
Mesoporous Supports ◽  
Acid Reduction

Reactions of N-substituted 2-aminopyridines with chloroacetyl chloride; Formation of a new series of heterocyclic betaines: 1-Substituted 4-chloromethyl-2-oxopyrido[1,2-a]pyrimidin-5-ium-3-olates

1989 ◽  
Vol 54 (5) ◽  
pp. 1376-1387 ◽  
Author(s):  
Hana Hulinská ◽  
Miloš Buděšínský ◽  
Jiří Holubek ◽  
Oluše Matoušová ◽  
Hana Frycová ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Sodium Borohydride ◽  
Nmr Spectra ◽  
Aqueous Ethanol ◽  
Hydrogen Bromide ◽  
Chloroacetyl Chloride ◽  
Gastric Lesions ◽  
Substitution Reactions ◽  
Reaction Compound ◽  
C Nmr

N-(2-Pyridyl)-2-chloroacetamide reacted with 1-methylpiperazine and gave the expected compound III. Attempts at preparing the N-substituted N-(2-pyridyl)-2-chloroacetamides by reactions of N-substituted 2-aminopyridines with chloroacetyl chloride in benzene in the presence of N,N-dimethylacetamide were negative and took an unexpected course. 2-Anilinopyridine and 2-(cyclohexylamino)pyridine afforded compounds which were identified by 1H and 13C NMR spectra as the heterocyclic betaines IVa and IVb. 2-(1-Butylamino)pyridine, 2-(benzylamino)pyridine and 2-(2-phenylethylamino)pyridine gave similarly compounds IVc-IVe. The chloromethyl compounds IVa-IVe underwent normal substitution reactions with 1-methylpiperazine and gave the methylpiperazino compounds Va-Ve. Attempts to reduce the betaines with sodium borohydride in aqueous ethanol proceeded in one case as the hydrogenolytic displacement of the chlorine atom with hydrogen (product VIa), in another case as ethanolysis (product VIIb). Formation of VIb by treatment of IVb with hydrogen bromide in boiling acetic acid is probably the result of a disproportionation reaction. Compound III (dimaleate VÚFB-17 103) was practically equipotent with pirenzepine (I) as an anti-ulcer agent in the test of indomethacine-induced gastric lesions in rats but was much weaker in tests for antocholinergic and antisecretory activity.

Acetic Acid Reduction by H2 on Bimetallic Pt–Fe Catalysts

2002 ◽  
Vol 209 (1) ◽  
pp. 87-98 ◽  
Author(s):  
Willy Rachmady ◽  
M.Albert Vannice
Keyword(s):  
Acetic Acid ◽  
Fe Catalysts ◽  
Acid Reduction

Synthesis and Antimicrobial Evaluation of Some New 2-(6-Oxo-5,6- dihydro[1,3]thiazolo[3,2-b]-2-aryloxymethyl-1,2,4-triazol-5-yl)-Narylacetamides

2010 ◽  
Vol 65 (5) ◽  
pp. 617-624 ◽  
Author(s):  
Prajwal L. Lobo ◽  
Boja Poojary ◽  
Kumsi Manjunatha ◽  
Nalilu Suchetha Kumari
Keyword(s):  
Acetic Acid ◽  
Antifungal Activity ◽  
Spectral Data ◽  
Good Yield ◽  
Antibacterial And Antifungal Activity ◽  
Acid Media ◽  
Antimicrobial Evaluation ◽  
Antibacterial And Antifungal

A series of 2-(6-oxo-5,6-dihydro[1,3]thiazolo[3,2-b]-2-aryloxymethyl-1,2,4-triazol-5-yl)-Narylacetamides 6 were synthesized in good yield by condensing 5-aryloxymethyl-4H-1,2,4-triazole- 3-thiol 5 with various substituted N-phenyl-maleimides in acetic acid media. The newly synthesized compounds were characterized by spectral data and tested for their in vitro antibacterial and antifungal activity against a variety of microorganisms.

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