Reactions of 3-cyano-1-methylquinolinium methyl sulphate with some C-acids and with p-nitroaniline

1981 ◽  
Vol 46 (2) ◽  
pp. 503-505 ◽  
Author(s):  
Oldřich Kocián ◽  
Miloslav Ferles
Keyword(s):  
Sodium Methoxide ◽  
Ethyl Cyanoacetate ◽  
Derivatives Of

The action of malononitrile, ethyl cyanoacetate, dibenzoylmethane and/or p-nitroaniline on compound I in the presence of sodium methoxide gives rise to derivatives of 3-cyano-1-methyl-1,4-dihydroquinoline, II and III

Preparation of Chloro and Sulfanyl Derivatives of 1-(2-Deoxy-4-C-hydroxymethyl-α-L-threo-Pentofuranosyl)uracil

1997 ◽  
Vol 62 (7) ◽  
pp. 1114-1127 ◽  
Author(s):  
Hubert Hřebabecký ◽  
Jan Balzarini ◽  
Antonín Holý
Keyword(s):  
Nucleophilic Substitution ◽  
Hydrogen Chloride ◽  
Thionyl Chloride ◽  
Sodium Methoxide ◽  
Thioacetic Acid ◽  
Uracil Derivatives ◽  
Derivatives Of ◽  
Hiv 1

3'-Chloro and 3'-acetylsulfanyl derivatives of 1-(2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil were prepared by reaction of 2,3'-anhydro-1-{5'-O-benzoyl-4'-C-[(benzoyloxy)methyl]-2'-deoxy-α-L-erythro-pentofuranosyl}uracil (3) with hydrogen chloride and thioacetic acid, respectively. The reaction with hydrogen chloride gave a mixture of N-1 and N-3 substituted uracil derivatives 12 and 14. Reaction of 1-{3-O-benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-α-L-threo-pentofuranosyl}uracil (7) with thionyl chloride and subsequent debenzoylation afforded 1-(4-C-chloromethyl-2-deoxy-β-D-erythro-pentofuranosyl)uracil (19). Nucleophilic substitution with lithium thioacetate, followed by deacylation, converted 1-{3-O-benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-toluenesulfonyl-α-L-threo-pentofuranosyl}uracil (9) into 1-(2-deoxy-4-C-sulfanylmethyl-β-D-erythro-pentofuranosyl)uracil (21). The obtained thiols were oxidized with iodine or air to give 1,1'-[disulfandiylbis(2,3-dideoxy-4-hydroxymethyl-α-L-threo-pentofuranose-3,1-diyl]di(pyrimidine-2,4-(1H,3H)-dione) (17) and 1,1'-[disulfandiylbis(2,5-dideoxy-4-hydroxymethyl-α-L-threo-pentofuranose-5,1-diyl]di(pyrimidine-2,4(1H,3H)-dione) (22). Reaction of 1-{3-acetylsulfanyl-5-O-methanesulfonyl-4-C-[(benzoyloxy)methyl]-2,3-dideoxy-α-L-threo-pentofuranosyl)}uracil (24) with methanolic sodium methoxide afforded 1-(3,5-anhydro-2,3-dideoxy-4-C-hydroxymethyl-3-sulfanyl-α-L-threo-pentofuranosyl)uracil (25). The same reagent was used in the preparation of 1-(3,5-anhydro-2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil (26) from 1-{4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-toluenesulfonyl-α-L-threo-pentofuranosyl}uracil (8). From the series of 4'-substituted 2'-deoxyuridine derivatives, synthesized in this study, solely the 4'-chloromethyl derivative 19 and the oxetane derivative 26 exhibited an appreciable activity against HIV-1 and HIV-2.

scholarly journals Synthesis and anticonvulsant activity of 6-methyl-2-((2-oxo-2-arylethyl)thio)pyrimidin-4(3 H)-one derivatives and products of their cyclization

Pharmacia ◽  
2019 ◽  
Vol 66 (3) ◽  
pp. 141-146
Author(s):  
Hanna Severina ◽  
Olga O. Skupa ◽  
Natalya I. Voloshchuk ◽  
Marharyta M. Suleiman ◽  
Victoriya A. Georgiyants
Keyword(s):  
Sulphuric Acid ◽  
Anticonvulsant Activity ◽  
Sodium Methoxide ◽  
Structure Activity ◽  
Phenacyl Bromides ◽  
Pharmacological Screening ◽  
High Yields ◽  
Derivatives Of

The alkylation of 6-methyl-2-thioxo-2,3-dihydro-1H-pyrimidine-4-one phenacyl bromides under different conditions was investigated. It was found that during the reaction in the medium of DMF/K2CO3 a mixture of 2-(2-aryl-2-oxoethyl)thio-6-methyl-pyrimidine-4(3H)-one and 3-hydroxy-3-aryl-7-methyl-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-5-one was formed. The holding of the resulting mixture in the concentrated sulphuric acid leads to the formation of cyclization products - derivatives of 3-aryl-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one with high yields. Individual S-alkylated derivatives – 2-(2-aryl-2-oxoethyl)thio-6-methyl-pyrimidine-4(3H)-one - were obtained by reacting in methanol in the presence of sodium methoxide. Pharmacological screening of synthesized compounds for anticonvulsant activity on the model of pentylenetetrazole seizures in rats was carried out and some regularity “structure-activity” was established.

23.—The Synthesis of Derivatives of Acenaphthenone

1974 ◽  
Vol 71 (4) ◽  
pp. 279-283 ◽  
Author(s):  
Michael J. Bedford ◽  
Douglas A. Crombie
Keyword(s):  
Polymeric Material ◽  
Malonic Acid ◽  
Hydroxy Acid ◽  
Ethyl Cyanoacetate ◽  
Geometric Isomer ◽  
Unsaturated Ester ◽  
Image Position ◽  
Derivatives Of

Acenaphthenequinone (I) condensed with ethyl cyanoacetate in ethanol to give the unsaturated ester (IIIb) while condensation with malonic acid in toluene in the presence of diethylamine gave the hydroxy acid (IIa). Esterification of this acid gave an ester (IIb) which could also be obtained by condensation of acenaphthenequinonewith ethyl hydrogen malonate. The acid (IIa) on dehydration gave 2-oxo-Δ1,α-acenaphtheneacetic acid (IIIa) of m.p. 230°C. This result seems to be in conflict with that of Rodionov and Federova (1950) who reported a m.p. of 160° for the acid (IIIa) which they obtained directly by condensation of acenaphthenequinone with malonic acid in ethanol in the presence of ammonia. Our efforts to repeat their result gave only impure polymeric material and it seems unlikely, therefore, that their product was simply the geometric isomer of our acid.

Synthetic use of the ribosyl derivatives of 2,4- and 2,5-thiazolidinediones

1979 ◽  
Vol 44 (5) ◽  
pp. 1475-1482 ◽  
Author(s):  
Hubert Hřebabecký ◽  
Zdeněk Točík ◽  
Jiří Beránek
Keyword(s):  
Hydrazine Hydrate ◽  
Hydrogen Chloride ◽  
Sodium Methoxide ◽  
Aqueous Ammonia ◽  
Hydroxylamine Hydrochloride ◽  
Acetyl Derivative ◽  
High Yield ◽  
Derivatives Of ◽  
Methanolic Ammonia

On ribosidation of 2,4-thiazolidinedione (2,5-thiazolidinedione, respectively), the 3-β-D-ribofuranosyl derivative is formed in high yield, either the benzoyl derivative Ia (IIa) or the acetyl derivative Ib (IIb). The unsubstituted ribosyl derivative Ic is formed from the acetyl derivative Ib by methanolic hydrogen chloride. The benzoylated ribosyl-2,4-thiazolidinedione Ia affords the benzoylated ribosylurea III on reaction with aqueous ammonia, the hydroxyethylurea derivative IVa with 2-aminoethanol, the semicarbazide derivative Va with hydrazine hydrate, the ribosylhydroxyurea derivative VIa on reaction with hydroxylamine hydrochloride and triethylamine, the benzoyl derivative of ribosylbiuret VII with O-methylisourea hydrochloride and triethylamine, and (analogously) ribosylisothiobiuret VIII with S-methylisothiourea. Methanolysis of the benzoyl derivative of hydroxyethylurea IVa with sodium methoxide affords the unprotected riboside IVb. Ribosylhydroxyurea VIb is formed on debenzoylation of compound VIa with methanolic ammonia. Acetylation of compound VIb furnishes the pentaacetyl derivative VIc.

scholarly journals A new and facile synthetic approach to substituted 2-thioxoquinazolin-4-ones by the annulation of a pyrimidine derivative

2010 ◽  
Vol 6 ◽  
pp. 1056-1060 ◽  
Author(s):  
Nimalini Devi Moirangthem ◽  
Warjeet Singh Laitonjam
Keyword(s):  
Ethyl Cyanoacetate ◽  
Pyrimidine Derivative ◽  
Synthetic Approach ◽  
Facile Synthesis ◽  
Benzenoid System ◽  
Active Methylene Compounds ◽  
Pyrimidine Moiety ◽  
Derivatives Of ◽  
Active Methylene

A new and facile synthesis of 2-thioxoquinazolin-4-ones by introducing a benzenoid system in the pyrimidine moiety by reacting ethoxymethylene derivatives of 1,3-diarylthiobarbituric acids (DTBA) with active methylene compounds, such as malononitrile and ethyl cyanoacetate, in presence of ZnCl2 has been developed.

Synthesis of 5-cyanopyrazolo[3,4-b]pyridines in the reaction of 5-amino-3-methyl-1-phenylpyrazole with arylidene derivatives of malonodinitrile and ethyl cyanoacetate

1999 ◽  
Vol 36 (5) ◽  
pp. 1311-1316 ◽  
Author(s):  
Jairo Quiroga ◽  
Mario Alvarado ◽  
Braulio Insuasty ◽  
Rodolfo Moreno ◽  
Enrique Raviña ◽  
...  
Keyword(s):  
Ethyl Cyanoacetate ◽  
Derivatives Of

Preparation of the 2,3-anhydro-4,6-O-benzylidene derivatives of methyl α- and β-D-talopyranoside and of methyl α-D-gulopyranoside

1980 ◽  
Vol 33 (5) ◽  
pp. 1021 ◽  
Author(s):  
JL Frahn
Keyword(s):  
Dimethyl Sulfoxide ◽  
Sodium Methoxide ◽  
Room Temperature ◽  
Derivatives Of

Instructions are given for preparing the title compounds in reproducibly good yields from the appropriate anomer of methyl 4,6-O-benzylidene-2,3-di-O-tosyl-D-galactopyranoside. The α-anomer is converted into a mixture of the anhydro-α-taloside and anhydro-α- guloside by reaction with sodium methoxide in dimethyl sulfoxide as solvent at room temperature. The β-anomer forms the anhydro-β-taloside under similar conditions but with dioxan as solvent for the reactants.

Synthesis and Biological Effects of 9-(3-Hydroxy-2-phosphonomethoxypropyl) Derivatives of Deazapurine Bases

1993 ◽  
Vol 58 (6) ◽  
pp. 1403-1418 ◽  
Author(s):  
Hana Dvořáková ◽  
Antonín Holý ◽  
Petr Alexander
Keyword(s):  
Acid Hydrolysis ◽  
Sodium Methoxide ◽  
Potent Inhibitor ◽  
Biological Effects ◽  
Side Chain ◽  
Cesium Carbonate ◽  
Phosphonic Acids ◽  
Dna Viruses ◽  
Derivatives Of ◽  
Subsequent Acid

Analogs of antiviral 9-(S)-(3-hydroxy-2-phosphonomethoxypropyl)adenine (HPMPA, I), containing modified purine bases 3-deazaadenine XII, 1-deazaadenine XIV, 7-deaz-7-cyanoaadenine XXXII and 3-deazaguanine XXXVIII, were prepared by alkylation of the bases with synthon XVII, containing preformed structure of the side chain, in the presence of cesium carbonate. The obtained protected derivatives were deblocked successively with sodium methoxide and bromotrimethylsilane to give phosphonic acids XII, XIV, XXXII and XXXVIII. Compounds XII, XIV and XVI were also prepared from (S)- or (R)-9-(2,3-dihydroxypropylderivatives VI, VII and XV by the reaction with chloromethanephosphonyl dichloride, isomerization of the arising 2'- and 3'-chloromethanephosphonates and conversion of the 3'-isomers into the phosphonic acids in alkaline medium. The 3-deaza analog XII was also prepared by ditritylation of VI, reaction with bis(2-propyl) tosyloxymethanephosphonate (XXII), subsequent acid hydrolysis and reaction with bromotrimethylsilane. 3-DeazaHPMPA (XII) is a potent inhibitor of DNA viruses (HSV-1, HSV-2, VZV, CMV) and exhibits activity against Plasmodium sp.

Use of malonic acid derivatives for the construction of substituted side chains in the position 17β of steroids

1982 ◽  
Vol 47 (4) ◽  
pp. 1240-1251 ◽  
Author(s):  
Pavel Drašar ◽  
Vladimír Pouzar ◽  
Ivan Černý ◽  
Miroslav Havel ◽  
Sofia N. Ananchenko ◽  
...  
Keyword(s):  
Malonic Acid ◽  
Ethyl Cyanoacetate ◽  
Diethyl Malonate ◽  
Side Chain ◽  
Knoevenagel Reaction ◽  
Side Chains ◽  
Condensation Products ◽  
Malonic Acid Derivatives ◽  
Derivatives Of ◽  
Dioxane Ring

Using the Knoevenagel reaction condensation products of 3β-acetoxyandrost-5-en-17-one with diethyl malonate, ethyl cyanoacetate and malononitrile were prepared which converted to derivatives of 3β-hydroxypregn-5-en-21-oic acid. Reductions and oxidations of the double bonds in the positions 5,6 and 17,20 and the stereochemistry at atoms C(17) and C(20) of some derivatives were also investigated. From derivatives of 23,24-dinorchola-5,17(20)-diene-21,22-diol compounds with a 1,3-dioxane ring in the side chain were prepared.

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