An efficient synthesis of 3-alkyl-2-diversity-substituted benzofuro[3,2-d]pyrimidin-4(3H)-one derivatives

2019 ◽  
Vol 43 (5-6) ◽  
pp. 201-204 ◽  
Author(s):  
Hong-Mei Wang ◽  
Tian-Shuai Wang ◽  
Sheng-Jie He ◽  
Zong-Yun Chen ◽  
Yang-Gen Hu
Keyword(s):  
Mass Spectrometry ◽  
Sodium Ethoxide ◽  
Catalytic Amount ◽  
Alkyl Halides ◽  
Efficient Synthesis ◽  
Pyrimidine Derivatives ◽  
Excess Carbon ◽  
H Nmr ◽  
Aliphatic Esters ◽  
C Nmr

Benzofuro[3,2- d]pyrimidine derivatives are prepared using aza-Wittig reactions of iminophosphoranes with n-butyl isocyanate at 40–50 °C to give carbodiimide intermediates, which are reacted with nitrogen-oxygen-containing nucleophiles to give 3-alkyl-2-amino (aryloxy/alkoxy)-benzofuro[3,2- d]pyrimidin-4(3 H)-ones in satisfactory yields in the presence of a catalytic amount of sodium ethoxide or K2CO3. The iminophosphorane also reacts directly with excess carbon disulfide, followed by n-propylamine; further reaction with alkyl halides or halogenated aliphatic esters in the presence of anhydrous K2CO3 produces the corresponding 2-alkylthio-3-n-propyl-benzofuro[3,2- d]pyrimidin-4(3 H)-ones in good yields. Their structures of the products are confirmed by 1H NMR, 13C NMR, mass spectrometry, infrared and elemental analysis.

scholarly journals Synthesis and antitumor activity of some novel thiophene, pyrimidine, coumarin, pyrazole and pyridine derivatives

2017 ◽  
Vol 67 (1) ◽  
pp. 15-33 ◽  
Author(s):  
Mohammed Albratty ◽  
Karam Ahmed El-Sharkawy ◽  
Shamsher Alam
Keyword(s):  
Antitumor Activity ◽  
Sodium Ethoxide ◽  
Ethyl Cyanoacetate ◽  
Catalytic Amount ◽  
Inhibitory Effect ◽  
Pyridine Derivatives ◽  
Pyrimidine Derivatives ◽  
H Nmr ◽  
One Step ◽  
Benzene Diazonium

Abstract 2-Cyano-N-(thiazol-2-yl) acetamide (2a) and 2-cyano-N-(oxazol- 2-yl) acetamide (2b) were obtained via the reaction of ethyl cyanoacetate with either 2-aminothiazole (1a) or 2-aminooxazole (1b). The formed products were directed toward the reaction with cyclopentanone and elemental sulfur in the presence of triethylamine to give cyclopenta[b]thiophene derivatives (3a,b). The latter products were reacted with either ethyl cyanoacetate or malononitrile to form compounds 4a,b and 5a,b, respectively. Compounds 4a,b were aimed at synthesizing some heterocyclic compounds; thus internal cyclization reactions were introduced to form compounds 6a,b. Also, compounds 4a,b reacted with salicylaldehyde, hydrazine derivatives and either urea or thiourea to produce coumarin derivatives (7a,b), pyrazole derivatives (8a-d) and pyrimidine derivatives (9a-d), respectively. Reaction of either benzaldehyde or benzene diazonium chloride (11) with compounds 4a,b afforded compounds 10a,b and 12a,b, respectively. On the other hand, compounds 5a,b underwent internal cyclization to form pyrimidine derivatives 13a,b. Also, when compounds 5a,b reacted with either ethyl cyanoacetate or malononitrile, they gave pyridine derivatives (15a-d) through the formation of intermediates (14a-d). Finally, formation of fused pyrimidine derivatives (17a,b) was achieved through the reaction of compounds 5a,b and salicylaldehyde applying two different pathways. The first pathway used a catalytic amount of piperidine to form compounds 16a,b; the latter products underwent cyclization to give compounds 17a,b. The second pathway, using a catalytic amount of sodium ethoxide solution directly in one step, afforded compounds 17a,b. Structures of the newly synthesized compounds were established using IR, 1H NMR, 13C NMR and mass spectrometry and their antitumor activity was investigated. Some of these compounds showed promising inhibitory effects on three different cell lines. However, fused pyrimidine acetonitrile derivatives 6a and 6b exerted the highest inhibitory effect, comparable to that of doxorubicin.

The regioselective catalyst-free synthesis of bis-quinoxalines and bis-pyrido[2,3-b]pyrazines by double condensation of 1,4-phenylene-bis-glyoxal with 1,2-diamines

2018 ◽  
Vol 24 (4) ◽  
pp. 193-196 ◽  
Author(s):  
Mehdi Ahmadi Sabegh ◽  
Jabbar Khalafy
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
New Products ◽  
Proton Nuclear Magnetic Resonance ◽  
Efficient Synthesis ◽  
H Nmr ◽  
Ft Ir ◽  
C Nmr ◽  
Nuclear Magnetic

AbstractThe oxidation of 1,4-diacetylbenzene using several oxidizing agents gave 1,4-phenylene-bis-glyoxal in 61–85% yields. A convenient and efficient synthesis of bis-quinoxaline and bis-pyrido[2,3-b]pyrazine derivatives involves the double condensation of 1,2-diamines with 1,4-phenylene-bis-glyoxal in ethanol under reflux conditions. The structures of the new products were defined by proton nuclear magnetic resonance (1H NMR), carbon-13 nuclear magnetic resonance (13C NMR), Fourier-transform infrared spectroscopy (FT-IR) and mass spectrometry (MS).

Crystal structure of 3-chlorobenzo[b]thiophene-2-carbonyl chloride

2009 ◽  
Vol 2009 (7) ◽  
pp. 437-439 ◽  
Author(s):  
Sara Tarighi ◽  
Alireza Abbasi ◽  
Sara Zamanian ◽  
Alireza Badiei ◽  
Mahmood Ghoranneviss
Keyword(s):  
Crystal Structure ◽  
Mass Spectrometry ◽  
Cinnamic Acid ◽  
Thionyl Chloride ◽  
Structure Determination ◽  
X Ray ◽  
Packing Structure ◽  
H Nmr ◽  
Carbonyl Chloride ◽  
C Nmr

3-Chlorobenzo[b]thiophene-2-carbonyl chloride was synthesised from cinnamic acid and thionyl chloride. The single crystal X-ray structure determination confirmed the earlier proposed structure and the product was further characterised by 1H NMR, 13C NMR and mass spectrometry. The X-ray structure determination revealed two sets of symmetry related molecules along the b-axis that are loosely connected by relatively weak CH…π ( 3.626, 3.628 Å) interactions, giving rise to two infinite chains. The packing structure is dominated by Van der Waals forces between these chains. No significant π–π interactions are found in the crystal structure.

scholarly journals Chloro- and BF2bdk-substituted dithienylethene: Synthesis, photophysical properties, and optical switching behavior

2020 ◽  
pp. 174751982095141
Author(s):  
Zhiqiang Lu ◽  
Wenbo Yang ◽  
Yanhui Bai ◽  
Mo Wang ◽  
Zixu Li ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Optical Switching ◽  
High Resolution Mass Spectrometry ◽  
Photophysical Properties ◽  
Red Light ◽  
Switching Behavior ◽  
Polar Solvents ◽  
H Nmr ◽  
Resolution Mass ◽  
C Nmr

A novel chloro- and BF2bdk-substituted dithienylethene derivative, in which a chlorine atom and a difluoroboron β-diketonate (BF2bdk) group are appended at the termini of the dithienylethene core, is developed. The structure was confirmed by 1H NMR, 13C NMR, and high-resolution mass spectrometry (electrospray ionization). It displayed solvent-dependent photophysical properties, and blue/red light-triggered optical switching behavior in nonpolar or less polar solvents.

Synthesis, Generic Dyeing of Nindigo Derivatives on Unmodified Polypropylene; First Time Application in Dyeing Technology

2019 ◽  
Vol 19 (11) ◽  
pp. 7105-7111 ◽  
Author(s):  
Raju Penthala ◽  
Rangaraju Satish Kumar ◽  
Hyorim Kim ◽  
Gisu Heo ◽  
Young-A Son
Keyword(s):  
Mass Spectrometry ◽  
Polypropylene Fiber ◽  
Blue Color ◽  
Substituted Anilines ◽  
Simple Route ◽  
H Nmr ◽  
Dispersing Agent ◽  
Didodecyldimethylammonium Bromide ◽  
First Time ◽  
C Nmr

Hydrophobic nindigo dyes were designed and successfully synthesized from indigo by reacting with substituted anilines in a simple route. Four nindigo dyes were fruitfully analyzed by 1H NMR 13C NMR, electronic and mass spectrometry. Here, we have firstly introduced these nindigo dyes into dyeing area for the dyeing of unmodified polypropylene fiber in aqueous medium. Dyeing experiments has been performed by using didodecyldimethylammonium bromide dispersing agent to make dye-dispersant complex for enhancing the dispersion of dyes. All the dyes were displayed profound blue color hue on polypropylene. The dyeing efficiency and dye fixation order of the nindigo dyes are 3d > 3c ≥ 3b > 3a. Compound 3d having higher the hydrophobic character (logP ═ 7.04), so greater the dye ability on the polypropylene fiber and exhibiting deep coloration.

scholarly journals Synthesis of Novel Fluorescent Sensors Based on Naphthalimide Fluorophores for the Highly Selective Hg2+-Sensing

2015 ◽  
Vol 2015 ◽  
pp. 1-9 ◽  
Author(s):  
Yordkhuan Tachapermpon ◽  
Pornthip Piyanuch ◽  
Narupon Prapawattanapol ◽  
Kanjarat Sukrat ◽  
Kullatat Suwatpipat ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Fluorescent Sensors ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
One Pot ◽  
H Nmr ◽  
Sensitivity And Selectivity ◽  
New Sensors ◽  
Interfering Ions ◽  
C Nmr

With an aim to develop the new sensors for optical detection of Hg2+ions, two novel fluorometric sensors were designed and successfully prepared using 2-(3-(2-aminoethylsulfanyl)propylsulfanyl)ethanamine and one or twoN-methylnaphthalimide moieties (1and2). Sensor1was obtained viaN-alkylation,N-imidation and a one-pot nucleophilic aromatic substitution, andN-formylation of the amine, while sensor2was prepared viaN-alkylation,N-imidation, and nucleophilic aromatic substitution. The characterization, including1H NMR,13C NMR, and mass spectrometry, was then performed for1and2. The Hg2+-binding behaviors of the sensors were investigated in terms of sensitivity and selectivity by fluorescence spectroscopy. Sensor1especially provided the reversible and highly Hg2+-selective ON-OFF fluorescence behavior by discriminating various interfering ions such as Pb2+, Co2+, Cd2+, Mn2+, Fe2+, K+, Na+, and in particular Cu2+and Ag+with a detection limit of 22 ppb toward Hg2+ions.

scholarly journals Synthesis, antioxidant activity, and density functional theory study of catechin derivatives

RSC Advances ◽  
2017 ◽  
Vol 7 (85) ◽  
pp. 54136-54141 ◽  
Author(s):  
Jing Wang ◽  
Han Tang ◽  
Bo Hou ◽  
Pan Zhang ◽  
Qi Wang ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Density Functional Theory ◽  
Antioxidant Activity ◽  
Density Functional ◽  
Density Functional Theory Study ◽  
Functional Theory ◽  
H Nmr ◽  
C Nmr

Catechin derivatives were synthesized, and their structures were characterized by 1H-NMR, 13C-NMR, and mass spectrometry.

scholarly journals A Novel and Efficient Synthesis of [1,2,3]-Triazolyl Substituted Benzo[c]Coumarins and Evaluation of their Antimicrobial Activity

2016 ◽  
Vol 70 ◽  
pp. 1-11
Author(s):  
Neha N. Gohil ◽  
Kaushik N. Kundaliya ◽  
Dinkar I. Brahmbhatt
Keyword(s):  
Antimicrobial Activity ◽  
Fungal Pathogens ◽  
Sodium Acetate ◽  
Efficient Synthesis ◽  
Mass Spectral Data ◽  
Pyridinium Bromide ◽  
Mass Spectral ◽  
H Nmr ◽  
Anti Fungal ◽  
C Nmr

A series of novel [1,2,3]-triazolyl substituted benzo [c] coumarins have been synthesized by reacting various 3-coumarinoyl methyl pyridinium bromide salts with 1-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl) ethanones in the presence of sodium acetate in refluxing acetic acid. The structures of the synthesized compounds have been elucidated by IR,1H-NMR,13C-NMR and Mass spectral data. All the synthesized compounds have been screened for theirinvitroanti-bacterial and anti-fungal activities. Some of the compounds have been found to be active against some bacterial and fungal pathogens compared to standard drugs.

Ultrasound-assisted synthesis and antimicrobial activity of tetrazole-based pyrazole and pyrimidine derivatives

2018 ◽  
Vol 24 (1) ◽  
pp. 59-65 ◽  
Author(s):  
Vidya S. Dofe ◽  
Aniket P. Sarkate ◽  
Zarina M. Shaikh ◽  
Charansingh H. Gill
Keyword(s):  
Mass Spectrometry ◽  
Escherichia Coli ◽  
Nuclear Magnetic Resonance ◽  
Antimicrobial Activity ◽  
Antimicrobial Agents ◽  
Ultrasound Irradiation ◽  
Pyrimidine Derivatives ◽  
Ultrasound Assisted ◽  
C Nmr

Abstract New tetrazole-based pyrazole and pyrimidine derivatives were synthesized by an ultrasound irradiation method. All compounds were characterized by infrared spectroscopy (IR), 1H nuclear magnetic resonance (NMR), 13C NMR, mass spectrometry (MS) and elemental analysis and assessed in vitro for their efficacy as antimicrobial agents against four bacteria (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa) and two fungi (Candida albicans, Aspergillus niger). Compounds 8a, 8e, 9a, 9b and 9e show potent activity against the tested strains compared to the reference drugs chloramphenicol and clotrimazole.

The synthesis of hydrophobic 1-alkyl-1H,1′H-2,2′-bibenzo[d]imidazoles

2016 ◽  
Vol 22 (2) ◽  
pp. 99-102 ◽  
Author(s):  
Iwona Mądrzak-Litwa ◽  
Anna Turguła ◽  
Danuta Rusińska-Roszak ◽  
Aleksandra Borowiak-Resterna
Keyword(s):  
Elemental Analysis ◽  
Alkyl Halides ◽  
H Nmr ◽  
New Synthesis ◽  
C Nmr

AbstractNew synthesis of 1-alkyl-1H,1′H-2,2′- bibenzo[d]imidazoles 3 by alkylation of a disodium derivative of 1H,1′H-2,2′-bibenzo[d]imidazole 2a with alkyl halides is proposed. It is noteworthy that 1,1′-dialkylated byproducts 4 are formed in yields of <5%. The structure of all obtained compounds has been confirmed by 1H NMR, 13C NMR, and HRMS or elemental analysis.

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