Synthesis of New Arylsulfonylurea Derivatives of Saccharin

1993 ◽  
Vol 46 (6) ◽  
pp. 903 ◽  
Author(s):  
M Benicha ◽  
A Azmani ◽  
M Akssira ◽  
DT Hurst
Keyword(s):  
Ethyl Chloroformate ◽  
Excellent Yield ◽  
Derivatives Of

Some new sulfonylurea derivatives (2a-j) of saccharin have been obtained by the reaction of ethyl 3-oxo-1,2-benzisothiazole-2(3H)-carboxylate 1,1-dioxide (1) with the appropriate amine. Ethyl 3-oxo-1,2-benzisothiazole-2(3H)-carboxylate 1,1-dioxide was obtained, in excellent yield, by the reaction of ethyl chloroformate with saccharin.

Synthesis of 2'(3')-phosphates and 2'(3')-phosphorothioates of 5'-O-carboxymethylinosine and related compounds

1980 ◽  
Vol 45 (10) ◽  
pp. 2817-2829 ◽  
Author(s):  
Antonín Holý ◽  
Pavol Kois
Keyword(s):  
Acid Hydrolysis ◽  
Alkaline Hydrolysis ◽  
Phosphorus Oxychloride ◽  
Triethyl Phosphite ◽  
Subsequent Treatment ◽  
Disodium Salt ◽  
Ethyl Chloroformate ◽  
Streptomyces Aureofaciens ◽  
Derivatives Of ◽  
Related Compounds

5'-O-Carboxymethylinosine (IX) was prepared from disodium salt of 2',3'-O-isopropylideneinosine (VIII) by treatment with sodium chloroacetate, followed by acid hydrolysis. 5'-O-(2-Aminoethylamidocarbonylmethyl)inosine (XIII) was obtained by reaction of IX with p-nitrophenol and subsequent treatment with ethylenediamine. Action of triethyl phosphite on the compounds IX and XIII afforded the corresponding 5'-O-substituted 2'(3')-phosphites X and XIV which on reaction with trimethylsilyl chloride and sulfur gave the 2'(3')-phosphorothioates XI and XV. The compound IX was transformed by phosphorus oxychloride in 5'-O-carboxymethylinosine 2'(3')-phosphate (XII). Uridine, adenosine and inosine 2'(3')-phosphorothioates (Ia-Ic) were obtained from 2',3'-O-di-n-butylstannylene derivatives of the nucleosides IV by treatment with thiophosphoryl chloride followed by alkaline hydrolysis; inosine and guanosine 2'(3')-phosphorothioates (Ic,Id) were prepared by reaction of the corresponding 2'(3')-phosphites VIc, VId with trimethylsilyl chloride and sulfur. Cyclization of Ic and Id with ethyl chloroformate in the presence of tri-n-butylamine afforded inosine 2',3'-O,O-cyclophosphorothioate (VIIc) and the corresponding guanosine derivative VIId. Compounds VIIc and VIId are not cleaved by Streptomyces aureofaciens ribonuclease.

scholarly journals Different behavior of 3-nitrotyrosine and tyrosine toward perfluorinated reagents suitable for one-step preparation of volatile derivatives

2012 ◽  
Vol 77 (5) ◽  
pp. 667-683
Author(s):  
Radmila Pavlovic ◽  
Antonio Biondi ◽  
Maria Chiesa ◽  
Natasa Trutic ◽  
Mirjana Abramovic ◽  
...  
Keyword(s):  
Oxidative Stress ◽  
Amino Acids ◽  
Amino Acid ◽  
Simultaneous Analysis ◽  
Ethyl Chloroformate ◽  
Fluorinated Alcohols ◽  
One Step ◽  
Derivatives Of ◽  
Heptafluorobutyric Anhydride

In view to develop a gas-chromatographic (GC) determination of the 3-nitrotyrosine (NY)/tyrosine (Y) ratio as a marker of nitro-oxidative stress, different reagents were tested with the objective of obtaining a single volatile fluorinated product for each amino acid by a one-step derivatization procedure. The heptafluorobutyric anhydride (HFBA) /heptafluorobutanol (HFBOH) mixture proved unsuccessful for NY and Y simultaneous analysis. The reaction with different chloroformates [isobutyl chlorofomate (iBuCF) and ethyl chloroformate (EtCF)] in the presence of different perfluorinated alcohols such as trifluoroethanol (TFEOH) and HFBOH was investigated. Combination EtCF/fluorinated alcohols yielded derivatives of NY and Y as single peaks suitable to the GC determination of the NY/Y ratio. The different behaviour of two amino acids in the used reaction mixtures and the parameters influencing the results were discussed.

scholarly journals Non-covalent Li···H interaction in the synthesis of peri-disubstituted naphthalene proton sponges.

2019 ◽  
Author(s):  
Alexander S Antonov
Keyword(s):  
Reaction Mass ◽  
Excellent Yield ◽  
Proton Sponges ◽  
Derivatives Of

Non-covalent Li···H interaction was utilized as a tool for the second lithiation of 4-lithio-1,8-bis(dimethylamino)naphthalene with n-BuLi in the presence of TMEDA in hexane. Metallation proceeds with 100% selectivity in the second peri-position and with up to 90% yield. A series of 4,5-disubstituted derivatives of DMAN has been prepared in a good to excellent yield after quenching the reaction mass with different electrophiles.

Noncovalent Li···H Interaction in the Synthesis of peri-Disubstituted Naphthalene Proton Sponges

Synthesis ◽  
2019 ◽  
Vol 52 (01) ◽  
pp. 98-104 ◽  
Author(s):  
Alexander S. Antonov ◽  
Artyom A. Yakubenko
Keyword(s):  
Reaction Mass ◽  
Excellent Yield ◽  
Proton Sponges ◽  
Derivatives Of

Noncovalent Li···H interaction was utilised as a tool for the second lithiation of 4-lithio-1,8-bis(dimethylamino)naphthalene with n-BuLi in the presence of TMEDA in hexane. Metallation proceeds with 100% selectivity in the second peri-position and with up to 90% yield. A series of 4,5-disubstituted derivatives of 1,8-bis(dimethylamino)naphthalene has been prepared in good to excellent yield after quenching the reaction mass with different electrophiles.

The chemistry of aryllead tricarboxylates. Synthesis of some α-aryl α,β-unsaturated carbonyl compounds

1983 ◽  
Vol 36 (2) ◽  
pp. 311 ◽  
Author(s):  
RP Kopinski ◽  
JT Pinhey
Keyword(s):  
Carbonyl Compounds ◽  
Methyl Substituent ◽  
Excellent Yield ◽  
Derivatives Of

The treatment of 4-benzoyltetrahydrofuran-2,3-dione (2a) with 2 equiv. of phenyllead triacetate (3a) in chloroform gives 1,2-diphenylpropenone (4a) in excellent yield. This reaction has been investigated with a number of similar derivatives of tetrahydrofuran-2,3-dione and a number of aryllead triacetates. It has been found to be very sensitive to the nature of the substituent at C4, and it would appear to be limited to the synthesis of a-methylene carbonyl compounds since a 5-methyl substituent inhibits the reaction.

Aminoalkylidene and aminoalkyl derivatives of 6,11-dihydrodibenzo[b,e]thiepin-2- and -9-carbonitrile and 4,10-dihydrothieno[2,3-c]-1-benzothiepin-6-carbonitrile; Antidepressants with a new activity profile

1988 ◽  
Vol 53 (2) ◽  
pp. 340-360 ◽  
Author(s):  
Karel Šindelář ◽  
Jiří Holubek ◽  
Oluše Matoušová ◽  
Emil Svátek ◽  
Martin Valchář ◽  
...  
Keyword(s):  
Ethyl Chloroformate ◽  
Biochemical Tests ◽  
Hexamethylphosphoric Triamide ◽  
Geometrical Isomers ◽  
Saturated Compound ◽  
Cuprous Cyanide ◽  
The Individual ◽  
Mild Hydrolysis ◽  
Derivatives Of ◽  
Cyano Compounds

Starting from the bromo ketones VIIc, XIII, and XXIV and proceeding via the alcohols VIIIc, IXc, XIV, XVII, and XXVI, the olefinic compounds IIc (+ VI), Xc (+XI), XVc and XIXc(+XXc), and the saturated compound XVIc were prepared. The pairs of geometrical isomers were separated by crystallization of salts and the individual compounds Iic, Xc, XVc, XVIc, XIXc, and XXc were transformed by treatment with cuprous cyanide in hexamethylphosphoric triamide to the corresponding cyano compounds IIb, Xb, XVb, XVIb, XIXb, and XXb. Compound IIb was synthesized also from the ketone VIIc via the cyano ketone VIIb and the cyano carbinol VIIIb. The secondary amine IIIb was prepared from IIc by partial demethylation with ethyl chloroformate, the following hydrolysis to IIIc, protection of NH group with butyrolactone, the following treatment with cuprous cyanide, and deprotection by mild hydrolysis. The title compounds, which are the cyano analogues of antidepressants of the prothiadene series, showed in pharmacological and biochemical tests properties of potential antidepressants and more or less selective inhibitors of the 5-hydroxytryptamine uptake in the rat brain; at the same time they are rather strong central cholinolytics.

scholarly journals Synthesis of Some New Folic Acid-Based Heterocycles of Anticipated Biological Activity

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 368
Author(s):  
Ola A. Abu Ali ◽  
Hosam A. Saad ◽  
Bodor M. A. Al Malki
Keyword(s):  
Biological Activity ◽  
Folic Acid ◽  
Ethyl Pyruvate ◽  
Ethyl Cyanoacetate ◽  
Acid Hydrazide ◽  
Ethyl Chloroformate ◽  
Urea Derivatives ◽  
Fused Heterocycles ◽  
Amino Derivatives ◽  
Derivatives Of

To date, no fused heterocycles have been formed on folic acid molecules; for this reason, and others, our target is to synthesize new derivatives of folic acid as isolated or fused systems. Folic acid 1 reacted with ethyl pyruvate, triethyl orthoformate, ethyl chloroformate, thioformic acid hydrazide, and aldehydes to give new derivatives of folic acid 2–6a,b. Moreover, It reacted with benzylidene malononitrile, acetylacetone, ninhydrin, ethyl acetoacetate, ethyl cyanoacetate, and ethyl chloroacetate to give the pteridine fused systems 10–15, respectively. Ethoxycarbonylamino derivate 5 reacted with some nucleophiles containing the NH2 group, such as aminoguanidinium hydrocarbonate, hydrazine hydrate, glycine, thioformic acid hydrazide, and sulfa drugs in different conditions to give the urea derivatives 16–20a,b. Compound 4 reacted with the same nucleophiles to give the methylidene amino derivatives 21–24a,b. The fused compound 10 reacted with thioglycolic acid carbon disulfide, malononitrile, and formamide to give the four cyclic fused systems 25–30, respectively. The biological activity of some synthesized showed moderate effect against bacteria, but no effect shown towards fungi.

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