scholarly journals Enaminonitrile as Building Block in Heterocyclic Synthesis: Synthesis of Novel 4H-Furo[2,3-d][1,3]oxazin-4-one and Furo[2,3-d]pyrimidin-4(3H)-one Derivatives

2017 ◽  
Vol 2017 ◽  
pp. 1-6 ◽  
Author(s):  
Manal M. El-Shahawi ◽  
Ahmed K. El-Ziaty
Keyword(s):  
Acetic Anhydride ◽  
Building Block ◽  
Benzoyl Chloride ◽  
Heterocyclic Synthesis ◽  
Elemental Analyses ◽  
Nitrogen Nucleophiles

2-Amino-4,5-diphenylfuran-3-carbonitrile 1 was utilized as building block for the construction of new furo[2,3-d]pyrimidin-4(3H)-one derivative 2 and 4H-furo[2,3-d][1,3]oxazin-4-one derivative 3 via treatment with acetic anhydride and benzoyl chloride, respectively. The 4H-furo[2,3-d][1,3]oxazin-4-one derivative 3 was transformed into novel furo[2,3-d]pyrimidin-4(3H)-ones 4–8, tetrazolylfuran derivative 10, and furo[3,2-d]imadazolone derivative 11 via reaction with various nitrogen nucleophiles. The structure features of the synthesized compounds were established from their spectral and elemental analyses.

5-Aminouracil as a Building Block in Heterocyclic Synthesis: Part IV. One-pot Synthesis of 1H-Pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dione Derivatives Using Controlled Microwave Heating

2011 ◽  
Vol 66 (8) ◽  
pp. 843-849
Author(s):  
Raafat M. Shaker ◽  
Kamal U. Sadek ◽  
Ebtisam A. Hafez ◽  
Mohamed Abd Elrady
Keyword(s):  
Microwave Heating ◽  
Building Block ◽  
Heterocyclic Synthesis ◽  
One Pot ◽  
H Nmr ◽  
One Pot Synthesis ◽  
Elemental Analyses ◽  
C Nmr

An efficient and direct procedure for the synthesis of pyrrolo[2,3-d]pyrimidine-2,4-dione derivatives using controlled microwave heating has been described. The products were characterized by elemental analyses, IR, 1H NMR, 13C NMR and MS spectra.

scholarly journals 5-Aminouracil as a Building Block in Heterocyclic Synthesis: Part III. One-pot Synthesis of Novel Pyrimido[5,4-b]quinoline-2,4,9-triones and Pyrimido[5,4-c]isoquinolines

2010 ◽  
Vol 65 (12) ◽  
pp. 1485-1490 ◽  
Author(s):  
Raafat M. Shaker ◽  
Kamal U. Sadek ◽  
Ebtisam A. Hafez ◽  
Mohamed Abd Elrady
Keyword(s):  
Building Block ◽  
Heterocyclic Synthesis ◽  
One Pot ◽  
H Nmr ◽  
One Pot Synthesis ◽  
Elemental Analyses ◽  
Isoquinoline Derivatives ◽  
C Nmr

An efficient and direct procedure for the synthesis of pyrimido[5,4-b]quinoline-2,4,9-trione and pyrimido[5,4-c]isoquinoline derivatives has been described. The products were characterized by elemental analyses, IR, 1H NMR, 13C NMR and MS spectra.

5-Aminouracil as a Building Block in Heterocyclic Synthesis: Part I. One-pot Synthesis of Pyrimido[5,4-b]quinolin-2,4,9-triones under Microwave Irradiation without Catalyst

2008 ◽  
Vol 63 (12) ◽  
pp. 1431-1437 ◽  
Author(s):  
Raafat M. Shaker ◽  
Mohamed Abd Elrady
Keyword(s):  
Microwave Irradiation ◽  
Potassium Carbonate ◽  
Building Block ◽  
Anhydrous Potassium Carbonate ◽  
Nmr Spectra ◽  
Heterocyclic Synthesis ◽  
One Pot ◽  
One Pot Condensation ◽  
Elemental Analyses ◽  
C Nmr

A series of 6,7,8,10-tetrahydropyrimido[5,4-b]quinolin-2,4,9-(1H,3H,5H)-triones 6 were synthesized through one-pot condensation of 5-aminouracil, aldehydes and dimedone in DMF under microwave irradiation without catalyst. The products 6a, d were oxidized to the 7,8-dihydro-pyrimido- [5,4-b]quinolin-2,4,9-(1H,3H,6H)-triones 11a, b. Treatment of 6a, d and/or 11a, b with ethyl iodide in the presence of anhydrous potassium carbonate gave the ethylated derivatives 12a, b and 13a, b, respectively. The structures of the products were confirmed by elemental analyses, IR, MS, 1H, and 13C NMR spectra.

Functionally Substituted Enamines as Building Blocks in Heterocyclic Synthesis: Reactivity of Glyoxal Diphenylhydrazone toward Electrophilic Reagents

2005 ◽  
Vol 2005 (11) ◽  
pp. 729-732 ◽  
Author(s):  
Huwaida M. E. Hassaneen ◽  
Tayseer A. Abdallah ◽  
Hamdi M. Hassaneen ◽  
Mohamed H. Elnagdi
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Benzoyl Chloride ◽  
Phosphorus Oxychloride ◽  
Aromatic Aldehydes ◽  
Building Blocks ◽  
Secondary Amines ◽  
Vilsmeier Reaction ◽  
Heterocyclic Synthesis ◽  
Electrophilic Reagents

Glyoxalbis(phenylhydrazone) 1a reacts with aromatic aldehydes and secondary amines to yield either propan-1,2-dialdiphenylhydrazones 2 or arylazopyrazoles 7 depending on the nature of utilised aldehyde. The reactivity of 1a with phosphorus oxychloride (POCl3) and dimethylformamide (DMF) (Vilsmeier reaction) afforded the cinnolin-3-carbaldehyde phenylhydrazone 11. Compound 1a afforded also the tribenzoyl derivative 16 on treatment with benzoyl chloride. Only the diacetyl derivative 17 was produced on refluxing 1a in acetic anhydride. The diphenylhydrazone 20 was produced on treatment of 19, prepared via coupling 18 with benzenediazonium chloride followed by phenylhydrazine. This cyclised into pyrazole 21 on reflux in acetic acid.

N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part X. The First Pyrazolo[1,5-b][1,2,4,6]thiatriazine Derivatives and their Unusual Reactions with Acylating Agents

2013 ◽  
Vol 66 (11) ◽  
pp. 1323 ◽  
Author(s):  
Rebecca E. Norman ◽  
Michael V. Perkins ◽  
Andris J. Liepa ◽  
Craig L. Francis
Keyword(s):  
Acetic Anhydride ◽  
Benzoyl Chloride ◽  
Ring System ◽  
Analogous Reaction ◽  
Heterocyclic Synthesis

N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 underwent a regioselective reaction with 3-aminopyrazoles 2 to produce pyrazolo[1,5-b][1,2,4,6]thiatriazines 3, representatives of a new ring system. Attempted N-acylation of compounds 3 with acetic anhydride (or chloride) and benzoyl chloride in pyridine, only afforded 5-(pyridin-4-yl)-pyrazolo[1,5-b][1,2,4,6]thiatriazine derivatives 11. The analogous reaction with pyridazine led to the corresponding pyridazin-4-yl derivative.

5-Aminouracil as a Building Block in Heterocyclic Synthesis, Part II. One-pot Synthesis of Pyrido[3,2-d:6,5-dʹ]dipyrimidines under Microwave Irradiation without Catalyst

2009 ◽  
Vol 64 (10) ◽  
pp. 1193-1198 ◽  
Author(s):  
Raafat M. Shaker ◽  
Mohamed A. Ameen ◽  
Afaf M. Abdel Hameed ◽  
Mohamed Abd Elrady
Keyword(s):  
Microwave Irradiation ◽  
1H Nmr ◽  
13C Nmr ◽  
Building Block ◽  
Heterocyclic Synthesis ◽  
One Pot ◽  
Microwave Assisted ◽  
One Pot Synthesis ◽  
Elemental Analyses

An efficient and direct procedure for the synthesis of pyrido[3,2-d:6,5-dʹ]dipyrimidine derivatives under microwave-assisted conditions is been described. The structures of the products were characterized by elemental analyses, and their IR, 1H NMR, 13C NMR, and MS spectra.

scholarly journals 4-(3,4-Dichlorophenyl)-6-(Furan-2-yl)Pyrimidine-2-Thiol as Building Block in Heterocyclic Synthesis

2009 ◽  
Vol 5 (2) ◽  
pp. 669-677 ◽  
Author(s):  
M. A. EL-Hashash ◽  
Yaser Abdel-moemen El-badry ◽  
J. M. Morsy
Keyword(s):  
Hydrazine Hydrate ◽  
Building Block ◽  
Kinetic Control ◽  
Aminobenzoic Acid ◽  
Heterocyclic Synthesis ◽  
Experimental Conditions ◽  
One Pot ◽  
Nitrogen Nucleophiles

Pyrimidine-2-thiol (1) has been synthesized via one-pot, three component synthesis. Its behavior towards nitrogen nucleophiles like hydrazine hydrate, ethylamine, piperidine, and 2-aminobenzoic acid has been studied. A speculation to explain the activities of the thioamide-iminothiol equilibrium based on their thermodynamic and kinetic control under the experimental conditions were investigated. The hydrazinopyrimidine 2 and aminocarbamoyl derivative 8 were used as key starting materials for synthesis of some interesting nitrogen bridgehead compounds 10-13, hydrazones 14-16, and some mixed and non-mixed heterocyclic systems 17-19 respectively.

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).

DiphenylN-Sulfamoylcarbonimidate - A Versatile Building Block in Heterocyclic Synthesis

Synthesis ◽  
1991 ◽  
Vol 1991 (09) ◽  
pp. 753-758 ◽  
Author(s):  
Manfred Haake ◽  
Bernd Schümmelfeder
Keyword(s):  
Building Block ◽  
Heterocyclic Synthesis

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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