scholarly journals Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivatives

1999 ◽  
Vol 64 (11) ◽  
pp. 655-662 ◽  
Author(s):  
Samira Swelam ◽  
Abd El-Salam ◽  
Magdi Zaki
Keyword(s):  
Acetic Anhydride ◽  
Formic Acid ◽  
Hydrazine Hydrate ◽  
Carbon Disulfide ◽  
Nitrous Acid ◽  
Reaction Medium ◽  
Pyrimidine Derivatives ◽  
Elemental Analyses ◽  
Tetrazole Derivatives

Reaction of 2 with different reagents, namely formic acid, acetic anhydride and trichloroacetonitrile, yielded pyrazolo[3,4-d]pyrimidine derivatives 3, 5 and 6, respectively. Pyrazolo[3,4-d]pyrimidine m-thiazine(7) and 2,4-(1H,3H)dithione (8) derivatives were formed by the action of carbon disulfide on 2, depending on the reaction medium. Interaction of 7 with hydrazine hydrate yielded the aminoimino derivative 9 which reacted with acetic anhydride, triethyl orthoacetate and/or appropriate aldehydes to give 11, 12 and 13a,b, respectively. Methylation of compound 8 gave 14, which reacted with hydrazine hydrate to afford the monohydrazino derivative 15. Reaction of 15, with formic acid and nitrous acid afforded pyrazolo[4,3-e]triazolo[1,5-c]pyrimidine (16) and pyrazolo[4,3-e]tetrazolo-[1,5-c]pyrimidine (17) derivatives, respectively. The structures of products 3-17 were identified in light of their elemental analyses and spectra data.

Synthesis of Pyrimidine, Thiazolopyrimidine, Pyrimidotriazine and Triazolopyrimidine Derivatives and their Biological Evaluation

1999 ◽  
Vol 54 (6) ◽  
pp. 788-798 ◽  
Author(s):  
Fawzy A. Attaby ◽  
Sanaa M. Eldin
Keyword(s):  
Biological Activity ◽  
Acetic Anhydride ◽  
Formic Acid ◽  
Hydrazine Hydrate ◽  
Carbon Disulfide ◽  
Biological Evaluation ◽  
The Other ◽  
Ethyl Chloroformate ◽  
Heterocyclic Derivatives ◽  
Active Methylene

Pyrimidin-4-one-2-thione (3) was synthesized via the reaction of thiourea (1) with ethyl benzoylacetate (2) and was taken as a starting material for the present study via its reactions with the halogen-containing reagents 6a-d and lOa-c to give the corresponding thiazolopyrimidines 8, 9 and 12a-c. The 2-hydrazino derivatives 5 were synthesized either via the reaction of 3 or 4 with hydrazine hydrate. Compound 5 reacted with 6a-c and lOa-c to give the corresponding pyrimidotriazines 17a-c and 19 respectively. Also, compound 5 reacted with the active methylene-containing reagents 13 and 2a,b to give the corresponding 2-pyrazolopyrimidines 15 and 22a,b respectively. On the other hand, the triazolopyrimidines 21a,b and 30a,b were also obtained via the reaction of 5 with each of formic acid, acetic anhydride, ethyl chloroformate and carbon disulfide respectively. Some of the newly synthesized heterocyclic derivatives were tested for their biological activity

Fluorine-Containing Heterocycles: Part I. Synthesis of New 7-(2-thienyl)-9-Trifluoromethylpyrido[3′,2′:4,5]Thieno[3,2-d]Pyrimidines and Related Fused Tetracyclic Systems

2005 ◽  
Vol 2005 (3) ◽  
pp. 147-154 ◽  
Author(s):  
Etify A. Bakhite ◽  
Abdu E. Abdel-Rahman ◽  
Elham A. Al-Taifi
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Formic Acid ◽  
Hydrazine Hydrate ◽  
Methyl Iodide ◽  
Phosphorus Oxychloride ◽  
Diethyl Malonate ◽  
Triethyl Orthoformate ◽  
Dimroth Rearrangement ◽  
Ethyl Chloroacetate

3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carboxamide (3) and 2-carbonitrile analogue 5 were prepared by reaction of 3-cyano-6-(2-thienyl)-4-trifluoromethylpyridine-2(1H)-thione (1) with chloroacetamide or chloroacetonitrile respectively. Heating compound 3 with triethyl orthoformate led to the formation of pyridothienopyrimidinone derivative 6. Reaction of 6 with phosphorus oxychloride produced 4-chloropyrimidine derivative 7 which underwent some nucleophilic displacements upon treatment with thiourea, piperidine, morpholine or hydrazine hydrate to give the target 4-substituted pyridothienopyrimidines 8, 10a, 10b and 11 respectively. Reaction of compound 8 with methyl iodide or ethyl chloroacetate gave compounds 9a,b. The condensation of 3-amino-6-(2-thienyl)-4-trifluoromethyl-thieno[2,3-b]pyridine-2-carbonitrile (5) with triethyl orthoformate led to the formation of methanimidate derivative 21 which upon treatment with hydrazine hydrate gave the target 3-amino-3,4-dihydro-4-imino-7-(2-thienyl)-9-trifluoromethylpyrido[3′,2′:4,5] thieno[3,2-d]pyrimidine (22). The reactions of compounds 11 and 22 with some reagents namely; triethyl orthoformate, acetic anhydride, formic acid, acetic acid, acetylacetone benzaldehyde and/or diethyl malonate were carried out and their products were identified, in most cases as [1,2,4]triazolopyridothienopyrimidines via Dimroth rearrangement.

scholarly journals Design, Synthesis and Characterization of Novel Arylamides Containing 1,2,4-triazole Nuclei for Possible Antimicrobial Activity

2004 ◽  
Vol 1 (5) ◽  
pp. 228-230 ◽  
Author(s):  
S. R. Dhol ◽  
P. M. Gami ◽  
R. C. Khunt ◽  
A. R. Parikh
Keyword(s):  
Antimicrobial Activity ◽  
Hydrazine Hydrate ◽  
Carbon Disulfide ◽  
Acid Chloride ◽  
Potassium Hydroxide ◽  
Synthesis And Characterization ◽  
Design Synthesis ◽  
Elemental Analyses

Diphenyl aceto hydrazide on reaction with carbon disulfide and potassium hydroxide gave potassiumα,α-diphenyl acetamido dithiocarbamate, which on cyclisation with hydrazine hydrate yielded key intermediate 3-mercapto-4,N-amino-5-benzhydryl-1,2,4-triazoles. The key intermediate on condensation with different acid chloride afforded our titled compounds. The synthesised compounds have been confirmed elemental analyses and further supported by spectral data. All the synthesised compounds have been evaluated for theirin vitroin vitro antimicrobial activity.

Synthesis of 3-benzylxanthine and Lumazine Analogues

2005 ◽  
Vol 2005 (4) ◽  
pp. 262-266 ◽  
Author(s):  
El Sayed H. El Ashry ◽  
Shaker Youssif ◽  
Maged El Ahwany ◽  
Mohamed El Sanan
Keyword(s):  
Acetic Anhydride ◽  
Carbon Disulfide ◽  
Nitrous Acid ◽  
Acid Treatment ◽  
Aromatic Aldehydes ◽  
Diethyl Oxalate

Several xanthines (7–13) are prepared by the cyclisation of 1-benzyl-5,6-diaminouracil with single-carbon inserting agents such as aromatic aldehydes, formamides, acetic anhydride, carbon disulfide, and nitrous acid. Treatment of 6-amino-1-benzyl-5-nitrosouracil with anilinobenzylidene derivatives (14–18) affords 7-hydroxyxanthines (19–23). Cyclisation of the diaminouracil 3 with glyoxal, benzil, and diethyl oxalate leads to lumazines (25–28).

New heterocycles from thienopyridocinnolines

1998 ◽  
Vol 76 (4) ◽  
pp. 469-476 ◽  
Author(s):  
M ZA Badr ◽  
A A Geies ◽  
M S Abbady ◽  
A A Dahy
Keyword(s):  
Acetic Anhydride ◽  
Hydrazine Hydrate ◽  
Nitrous Acid ◽  
Ammonium Acetate ◽  
Carbon Disulphide ◽  
Sodium Ethoxide ◽  
Ring Closure ◽  
Ethyl Chloroformate ◽  
Intramolecular Ring

3-Cyano-4-(p-tolyl)pyrido[3,2-c]cinnolin-2(1H) thione 3 was reacted with α -halo ketones, esters, or amides to give the intermediates, S-alkylated products 5b-h, respectively, which underwent intramolecular ring closure reactions with ethanolic sodium ethoxide to give thienopyridocinnolines 6a-h. Pyrimidothienopyridocinnolines 9 and 11 were obtained by treatment of oxazino compound 8 with hydrazine hydrate and ammonium acetate. Treatment of hydrazino derivative 13 with acetylacetone, triethylorthoformate, carbon disulphide, ethyl chloroformate, and acetic anhydride afforded triazolopyrimidothienopyridocinnolines 14-16, 18, and 21, while with nitrous acid the corresponding tetrazolo compound 19 was produced.Key words: thienopyridocinnolines; their pyrimido, triazolopyrimido, and heteroannelated systems.

scholarly journals Expeditious synthesis of 1,3,4-oxadiazole derivatives via sydnones

2008 ◽  
Vol 73 (2) ◽  
pp. 131-138 ◽  
Author(s):  
Ravindra Kamble ◽  
B.S. Sudha ◽  
D.G. Bhadregowda
Keyword(s):  
Acetic Anhydride ◽  
Microwave Irradiation ◽  
Hydrazine Hydrate ◽  
Reaction Times ◽  
Elemental Analyses ◽  
Oxadiazole Derivatives

The clean cyclization of chalcones (1a-c/2a-c) with hydrazine hydrate under microwave irradiation afforded pyrazolines derivatised with sydnone (3d-i/4d-i), which underwent 1,3-dipolar cyclo-addition with acetic anhydride to form pyrazolines appended with 1,3,4-oxadiazoles (5g-l/6g-l). The newly synthesized compounds were confirmed by spectral and elemental analyses. In comparison to classical heating, the results indicate that microwave irradiation affords higher yields, shorter reaction times (4-12 min) and cleaner reactions.

Synthesis and Antimicrobial Activity Evaluation of Some Novel Hydrazone, Pyrazolone, Chromenone, 2-Pyridone and 2-Pyrone Derivatives

2017 ◽  
Vol 41 (11) ◽  
pp. 617-623 ◽  
Author(s):  
Saad R. Atta-Allah ◽  
Wael S. I. Abou-Elmagd ◽  
Kamal A. A. Kandeel ◽  
Magdy M. Hemdan ◽  
David S. A. Haneen ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Acetic Anhydride ◽  
Hydrazine Hydrate ◽  
Carbon Disulfide ◽  
Antimicrobial Activities ◽  
Condensation Products ◽  
Activity Evaluation ◽  
Nucleophilic Reagents ◽  
Nitrogen Nucleophiles

A cyanoacetohydrazide derivative underwent a series of reactions with different nucleophilic reagents, such as hydrazine hydrate, p-chlorobenzaldehyde and salicylaldehyde, to give the condensation products. In addition, an arylidene malononitrile was reacted with different nitrogen nucleophiles, such as hydrazine hydrate, thiocarbohydrazide and cyanoacetohydrazide, to afford the hydrazine, hydrazone and pyridin-2-one derivatives, respectively. Furthermore, a pyridin-2-one derivative was reacted with different carbon electrophiles, such as carbon disulfide, p-chlorobenzaldehyde and acetic anhydride. The antimicrobial activities of some of the compounds were examined.

Synthesis and Reactions of Some New 3-Amino-2-substituted Thieno[2,3-b]quinolines

1992 ◽  
Vol 57 (11) ◽  
pp. 2359-2366 ◽  
Author(s):  
Etify Abdel-Ghafar Bakhite
Keyword(s):  
Acetic Anhydride ◽  
Carbon Disulfide ◽  
Nitrous Acid ◽  
Aromatic Amines ◽  
Triethyl Orthoformate ◽  
Ethyl Iodide ◽  
Polycyclic Compounds

Reaction of 3-cyano-quinolin-2(1H)-thione (II) with ω-bromoacetophenones gave 3-amino-2-aroyl-thieno[2,3-b]quinolines (IVa-IVd). Whereas, interaction of II with chloroacetanilides yielded the corresponding thioesters Va-Vc which cyclized into 3-amino-2-arylcarbamoylthiene[2,3-b]quinolines (VIa-VIc) on treatment with ethoxide. Compounds VIa-VIc were reacted with nitrous acid, triethyl orthoformate and carbon disulfide to afford the fused polycyclic compounds VIIa-VIIc, VIIIa-VIIIc and IXa-IXc, respectively. Also treatment of IXa-IXc with ethyl iodide gave 3-ethylthio derivatives Xa-Xc. Moreover, refluxing of VIa-VIc with acetic anhydride resulted in the formation of oxazinone XI which recyclized into pyrimidinones XIIIa-XIIIc upon reaction with aromatic amines.

Syntheses and Cytotoxicity Screening of some Novel 1,2,4-Triazine Derivatives against Liver Carcinoma Cell Lines

2020 ◽  
Vol 17 ◽  
Author(s):  
W. Abd El-Fattah
Keyword(s):  
Acetic Anhydride ◽  
Cell Lines ◽  
Carcinoma Cell ◽  
Aromatic Aldehydes ◽  
Liver Carcinoma ◽  
Anticancer Activities ◽  
Carcinoma Cell Lines ◽  
Elemental Analyses ◽  
Triazine Derivatives ◽  
C Nmr

: In this work, 1,2,4-triazine derivatives were synthesized and evaluated for anticancer activities. Series of 1,2,4-triazine derivatives (4a, b) were prepared via the reaction of N-benzoyl glycine (1) with aromatic aldehydes in presence of fused sodium acetate and acetic anhydride to give 1,3-oxazolinone derivatives (2a, b), followed by condensation with 1-(ethoxycarbonyl) hydrazine (3) in glacial acetic acid. Compounds (4a, b) then reacted with acetic anhydride, ethyl chloroacetate and 2,4-dinitrophenyl hydrazine yielded the corresponding to N-acetyl derivatives (5a, b), N-(ethoxycarbonyl) methyl derivative (6) and 1,2-disubstituted hydrazine (7), respectively. The structures of the 1,2,4-triazine derivatives were confirmed by IR, 1H, 13C NMR, MS and elemental analyses. Anticancer activity of some 1,2,4-triazine derivatives (4-7) have been investigated. The results revealed that compounds 4a (IC50= 2.7μM), 5a (IC50= 1.5μM), and 5b (IC50= 3.9μM) show promising inhibitory growth efficacy compared to a standard antitumor drug (IC50= 4.6μM). These three compounds can be considered as potential agents against human hepatocellular carcinoma cell lines (HepG-2).

Basic Chromium(III) Carboxylates: Reactions of Chromium(III) Chloride with Some Carboxylic Acids

1979 ◽  
Vol 34 (10) ◽  
pp. 1369-1372 ◽  
Author(s):  
Ramesh Kapoor
Keyword(s):  
Acetic Anhydride ◽  
General Formula ◽  
Carboxylic Acids ◽  
Magnetic Measurements ◽  
Molar Conductance ◽  
Strong Affinity ◽  
Elemental Analyses

Abstract Anhydrous chromium(III) chloride reacts with pure carboxylic acids (RCOOH where R = CH3, C2H5, n-C3H7, CH2Cl, CHCl2 and CCl3) to give basic trinuclear chromium(III) carboxylates of the general formula [Cr3O(OOCR)6]+Cl-. The reaction of CrCl3 with acetic anhydride, however, gives a partially substituted product, CrCl(OOCCH3)2.The formation of basic carboxylates has been attributed to the strong affinity of Cr3+ ions for water that they can abstract it even from pure carboxylic acids. Their addition compounds with ammonia have also been prepared. The compounds have been characterized by their elemental analyses, IR, molar conductance and magnetic measurements.

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