Efficient synthetic access to novel indolo[2,3-b]quinoxaline-based heterocycles

2021 ◽  
Vol 18 ◽  
Author(s):  
Ahmed Abdou O. Abeed ◽  
Talaat I. El-Emary ◽  
Sarah Alharthi
Keyword(s):  
Organic Chemistry ◽  
Mass Spectrometry ◽  
Heterocyclic Compounds ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Melting Points ◽  
Internal Reference ◽  
Elemental Analyses ◽  
Ft Ir ◽  
Synthetic Routes

Background: This paper showed the synthetic capability of the indolo[2,3-b]quinoxaline nucleus to be provided as an excellent precursor for the synthesis of various heterocyclic compounds. These synthetic routes proceed via the formation of 3-(6H-indolo[2,3-b]quinoxalin-6-yl)propane hydrazide (2). The carbohydrazide 2 and its reactions with different reagents give five and six-membered rings, such as 1,3,4-thiadiazole, 1,3,4-oxadiazole, 1,2,4-triazole, and 1,2,4-triazine. Methods: All chemicals used in the current study were of analytical grade. Melting points were determined using an APP Digital ST 15 melting point apparatus and were uncorrected. FT-IR spectra were recorded on a Pye-Unicam SP3-100 and Shimadzu-408 spectrophotometers in KBr pellets and given in (cm-1) KBr. The NMR spectra were detected by a Bruker AV-400 spectrometer (400 MHz for 1H, 100 MHz for 13C and 40.55 MHz for 15N), Institute of Organic Chemistry, Karlsruhe, Germany. Chemical shifts were expressed as δ (ppm) with TMS as an internal reference. Mass spectrometry was provided on a Varian MAT 312 instrument in EI mode (70 eV). Results: The target compounds were obtained, and their structures were completely elucidated by various spectral and elemental analyses (Ft-IR, 1H-NMR, 13C-NMR, and mass spectrometry). Conclusion: The current work showed a view of the reactivity of the carbohydrazide group. The carbohydrazide 2 was obtained from the hydrazinolysis of carboethoxy compound 1 and exploited as a key intermediate to synthesize heterocyclic compounds with different rings.

A Facile Synthesis and Reactions of Some Novel Pyrazole-based Heterocycles

2019 ◽  
Vol 16 (3) ◽  
pp. 405-412 ◽  
Author(s):  
Ahmed A.O. Abeed ◽  
Talaat I. El-Emary ◽  
Mohamed S.K. Youssef
Keyword(s):  
1H Nmr ◽  
High Performance ◽  
Nmr Spectra ◽  
Melting Points ◽  
Facile Synthesis ◽  
Direct Titration ◽  
Elemental Analyses ◽  
Ft Ir ◽  
Active Methylene ◽  
Pyrazoline Derivative

<p>Aim and Objective: This work presents the synthetic capability and the exploitation of 1,3-diphenyl- 1H-pyrazole-4-carboxladehyde 1 and 5-diphenyl pyrazolyl-2-pyrazoline analogue 8 to serve as excellent precursors for the synthesis of substituted indol-2,3-dione, trizolo[3,4-a]benzazoles, thiazolo[2,3- a]benzimidazole-3-one, substituted 2-pyrazoline and pyrazole-substituted-pyrazolines using various reagents. </P><P> Materials and Methods: Using chemicals from Aldrich, Fluka, or Merck, and pure solvents, we apply the synthetic procedures for the synthesis of novel heterocycles. The melting points of these compounds were determined using APP. Digital ST 15 melting point apparatus. SP3-100 spectrophotometer recorded FT-IR spectra (KBr) (cm-1). NMR spectra (&#948;, ppm) were recorded on 400 MHz AVANCE-III High-Performance FT-NMR Spectrometer BRUCKER (Switzerland) and some 1H NMR spectra were recorded on Varian EM-360L NMR Spectrophotometer (90 MHz) (USA) in CDCl3 or DMSO-d6 as a solvent. Elemental analyses were carried out at a Vario EL C, H, N, and S Analyzer. Bromine was determined using direct titration method after carius combustion. </P><P> Results: The structures of the compounds were confirmed by IR, 1H NMR, 13C NMR, and elemental analyses. </P><P> Conclusion: 1,3-Diphenyl-1H-pyrazole-4-carboxladehyde 1 and 2-pyrazoline derivative 9 confirmed their importance in the synthetic organic chemistry. Depending on the formyl group of aldehyde 1 and active methylene of pyrazoline 8, we synthesized new series of heterocycles; indol-2,3-dione, trizolo[3,4-a]benzazole, thiazolo[2,3-a]benzimidazole-3-one and pyrazolyl-pyrazoline derivatives expecting their pharmacological applications. The targeted compounds were substantiated from its spectral data.</p>

Synthesis and Antimicrobial Evaluation of Some Novel Pyrimidine, Pyrazole, Chromene and Tetrahydrobenzo[b]thiophene Derivatives Bearing Pyrimidinthione Moiety

2020 ◽  
Vol 17 (7) ◽  
pp. 548-557
Author(s):  
Mohamed Ahmed Mahmoud Abdel Reheim ◽  
Ibrahim Saad Abdel Hafiz ◽  
Mohamed Ahmed Elian
Keyword(s):  
1H Nmr ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Bacterial Biofilm ◽  
1H Nmr Spectra ◽  
Internal Reference ◽  
Aluminum Sheets ◽  
Elemental Analyses ◽  
Antimicrobial Evaluation ◽  
Thiophene Derivatives

Aim and Objective: A novel collection of fused pyrimidine, pyridine, pyrazole, chromene and thiophene derivatives 2-30 have been newly synthesized by using the 1a, b as starting material. Fused pyrane exhibits a range of pharmacological activity such as cancer agents [1], antimicrobial [2-4], antioxidant [5], antiproliferative [6], cytotoxic activity [7], anticipated antitumor [8], antiparkinsonian [9] and anti-inflammatory [10]. Moreover, pyrane derivatives are well known for bacterial biofilm disruptor [11], anticonvulsant [12] and inhibitors of mycobacterium bovis [13]. Materials and Methods: All melting points were measured using the Akofler Block instrument and are uncorrected. IR spectra (KBr) were recorded on a FTIR 5300 spectrometer (υ, cm-1). The 1H-NMR spectra were recorded on a Varian Gemini spectrometer. The 1H-NMR spectra were run at 300, 400 MHz and 13C-NMR spectra were run at 100 MHz in DMSO-d6, CDCl3 as solvents. The chemical shifts are expressed in parts per million (ppm) by using tetramethylsilane (TMS) as an internal reference, 1000 EX mass spectrometer at 70 eV. The purity of synthesized compounds was checked by thin-layer chromatography (TLC) (aluminum sheets) using nhexane, EtOAc (9:1, V/V, 7:3 V/V) eluent. Elemental analyses were carried out by the Microanalytical Research Center, Faculty of Science, and Microanalytical Unit, Faculty of Pharmacy, Cairo University, Egypt. Results and Discussion: A novel series of azoles and azines were designed and prepared via the reaction of 7-amino- 5-(4-chlorophenyl)-4-phenyl-2-thioxo-2,5-dihydro-1H-pyrano- [2,3-d]pyrimidine-6-carbonitrile 1a and 7-amino-4,5- diphenyl-2-thioxo-2,5-dihydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile 1b with some electrophilic and nucleophilic reagents. The structures of target compounds were confirmed by elemental analyses and spectral data. The novel synthesized compounds showed good antimicrobial activity against the previously mentioned microorganisms. Conclusion: In conclusion, compounds 1a, 1b underwent ready cyclization to give fused heterocyclic compounds through reaction with different reagents and under different conditions and subjected to antimicrobial screening.

scholarly journals Spectroscopic (FT-IR, Raman, NMR) and DFT Quantum Chemical Studies on Phenoxyacetic Acid and Its Sodium Salt

2012 ◽  
Vol 27 ◽  
pp. 307-313 ◽  
Author(s):  
M. Samsonowicz ◽  
E. Regulska ◽  
W. Lewandowski
Keyword(s):  
Sodium Salt ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Dipole Moments ◽  
Population Analysis ◽  
Phenoxyacetic Acid ◽  
Geometrical Structures ◽  
Chemical Studies ◽  
Quantum Chemical Studies ◽  
Ft Ir

FT-IR, Raman, and NMR spectra of phenoxyacetic acid and its sodium salt were recorded and analyzed. Optimized geometrical structures of studied compounds were calculated by B3LYP/6-311++ method. The atomic charges were calculated by Mulliken, NPA (natural population analysis), APT (atomic polar tensor), MK (Merz-Singh-Kollman method), and ChelpG (charges from electrostatic potentials using grid-based method) methods. Geometric as well as magnetic aromaticity indices, dipole moments, and energies were also calculated. The theoretical wavenumbers and intensities of IR spectra as well as chemical shifts in and NMR spectra were obtained. The calculated parameters were compared with experimental characteristics of these molecules.

scholarly journals Synthesis of some Heterocyclic Compounds Derived from 2-Chloro-N-p-Tolylacetamide

2017 ◽  
Vol 27 (4) ◽  
Author(s):  
Hanan Gh Shaaban
Keyword(s):  
Heterocyclic Compounds ◽  
Acetyl Chloride ◽  
Aromatic Aldehydes ◽  
Melting Points ◽  
Ft Ir ◽  
Ethyl Amine

This research includes preparation of (2-chloro-N-p-tolylacetamide) (1) from the reaction of (p-aminotoluene) with chloro acetyl chloride. Compound (1) reacted with thiosemi carbazide and gave compound (2), and when compound (1) reacted with semicarbazide gave compound (3). While when compound (1) reacted with thiourea it produced compound (4).Compounds (2-4) when reacted with appropriate aromatic aldehydes or ketones produced Shiff bass (5-16), which in turn reacted with chloro acetyl chloride in the present of tri ethyl amine and dioxin gave β-lactam derivatives (14-22). The structures of these compounds were characterized from their melting points, FT-IR, and NMR. 

Utility of Diketone in Heterocyclic Synthesis: Synthesis of New Substituted Pyrimidines and Fused Pyrimidine of Potential Biosignificant Interest

2018 ◽  
Vol 15 (8) ◽  
pp. 1171-1181 ◽  
Author(s):  
Mohamed A.M.A. Reheim ◽  
Ibrahim S.A. Hafiz ◽  
Hend S.E.A. Rady
Keyword(s):  
1H Nmr ◽  
Elemental Analysis ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Biological Activities ◽  
1H Nmr Spectra ◽  
Internal Reference ◽  
Aluminum Sheets ◽  
Layer Chromatography

Aim and Objective: In this study, a new series of iminopyrimidine derivatives were synthesized from the reaction of the key intermediate 2-imino-6-phenyl-2,3-dihydropyrimidin-4(5H)-one 4 with a variety of electrophilic and nucleophilic reagents under a variety of mild conditions. The structures of the newly synthesized compounds were characterized on the basis of their elemental analysis and spectroscopic data. The antimicrobial activity of this series was evaluated in vitro and they showed either weak or moderate activities. Materials and Methods: All melting points were measured using Akofler Block instrument and are uncorrected. IR spectra (KBr) were recorded on FTIR 5300 spectrometer (υ, cm-1). The 1H NMR spectra were recorded on a Varian Gemini spectrometer. The 1H NMR spectra were run at 400 MHz and 13C NMR spectra were run at 100 MHz in DMSO-d6 as a solvent. The chemical shifts are expressed in parts per million (ppm) by using tetramethylsilane (TMS) as an internal reference. 1000 EX mass spectrometer at 70 eV. The purity of synthesized compounds was checked by Thin Layer Chromatography (TLC) (aluminum sheets) using n-hexane, ethyl acetate (7:3, V/V) eluent. Elemental analysis was carried out by the Microanalytical Research Center, Faculty of Science, and Microanalytical Unit, Faculty of Pharmacy, Cairo University, Egypt. Conclusion: In conclusion, compounds 4, 5 and 12 were used as efficient precursors for the synthesis of new heterocycles including 2-imino-2,3-dihydropyrimidine moiety with expected biological activities.

scholarly journals Synthesis of Some Heterocyclic Compounds Derived from 2-Mercapto Benzoxazole

2013 ◽  
Vol 10 (3) ◽  
pp. 766-778 ◽  
Author(s):  
Baghdad Science Journal
Keyword(s):  
Acetic Acid ◽  
Melting Point ◽  
Heterocyclic Compounds ◽  
Nmr Spectra ◽  
Ring Closure ◽  
Phenyl Isothiocyanate ◽  
Triazole Derivative ◽  
Active Methylene Compounds ◽  
Ft Ir ◽  
Active Methylene

New series of 2-mecapto benzoxazole derivatives (1-20) incorporated into fused to different nitrogen and suphur containing heterocyclic were prepared from 2-meracpto benzoxazole, when treated with hydrazine hydrate to afford 2-hydrazino benzoxazol (1). Compound (1) converted to a variety of pyridazinone andphthalazinone derivatives (2-4) by reaction with different carboxylic anhydride. Also, reaction of (1) with phenyl isothiocyanate and ethyl chloro acetate afforded 3-phenyl-1,3-thiazolidin-2,4-dione-2-(benzoxazole-2-yl-hydrazone) (6). Azomethines (7-10) were prepared through reaction of (1) with aromatic aldehyde, then (7, 8) converted to thaizolidinone derivatives (11, 12). Treatment of (1) with active methylene compounds afforded derivative (13). Reaction of (1) with CS2 and NaOH gave 1,2,4-triazole derivative (14). Treatment of (1) with p-bromophenancyl bromide afforded another 1,2,4-triazole (15). The reaction of 2-mercapto benzoxazole with chloro acetic acid gave (16) followed by refluxing (16) with ortho-amino aniline giving benzimidazol (17). Moreover, the reaction of 2-mercapto benzoxazole with ethyl chloroacetate afforded (18), and then reaction of (18) with thiosemicarbazide and 4% NaOH leads to ring closure giving 1,2,4-triazole derivative (20). All compounds were confirmed by their melting point, FT-IR, UV-Vis spectra and 1H-NMR spectra for some of them.

scholarly journals 4-[(3,4-Dimethoxybenzylidene)amino]-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

Molbank ◽  
10.3390/m1055 ◽  
2019 ◽  
Vol 2019 (1) ◽  
pp. M1055
Author(s):  
Soukhyarani Nayak ◽  
Boja Poojary
Keyword(s):  
Mass Spectrometry ◽  
Inhibitory Action ◽  
Noncovalent Interactions ◽  
Catalytic Amount ◽  
13C Nmr Spectroscopy ◽  
Target Compound ◽  
Solid Product ◽  
1H And 13C Nmr ◽  
Elemental Analyses ◽  
Ft Ir

4-Amino-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (1) upon treatment with 3,4-dimethoxybenzaldehyde in 10 mL of absolute ethanol in the presence of a catalytic amount of acetic acid produced the target compound 4-[(3,4-dimethoxybenzylidene)amino]-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (2) in 80% yield. The obtained solid product was recrystallized from ethanol. The compound was characterized by elemental analyses, mass spectrometry, FT-IR, 1H and 13C-NMR spectroscopy. To study the binding interactions of the compound with receptor, it was docked with the human prostaglandin reductase (PTGR2). The docking pose and noncovalent interactions gave insights into its plausible inhibitory action.

scholarly journals Synthesis , Characterization and Biological activity of new derivatives of Chromen-2-one

2018 ◽  
Vol 15 (1) ◽  
pp. 6130-6135
Author(s):  
Aziz Behrami
Keyword(s):  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
Nmr Spectra ◽  
13C Nmr Spectra ◽  
Melting Points ◽  
Benzenesulfonyl Chloride ◽  
Bacterial Cultures ◽  
Escherchia Coli ◽  
Elemental Analyses ◽  
Derivatives Of

We report the organic syntheses of new derivatives  from Chromen-2-one and their  antibacterial activity. Compounds  4-[Acetyl-(2-oxo-2H-chromen-4-yl)-amino]- benzenesulfonyl chloride 1a, 4-[Acetyl-(2-oxo-3-phenylsulfamoyl-2H-chromen-4-yl)-amino]-benzenesulfonyl chloride 2a , 2-{4-[Acetyl-(4-chlorosulfonyl-phenyl)-amino]-2-oxo-3-phenylsulfamoyl-2H-chromen-7-ylamino}-benzoic acid  3a. All Structures have been synthesized and characterized using melting points , IR spectra , 1H-NMR, 13C-NMR spectra , and elemental analyses  . The purified synthesized compounds (1a,2a,3a), at contcentrations 2,3,5 mg/ml was tested for their  antibacterial activity against three bacterial cultures ;Staphylococcus aureus, Escherchia coli and Bacillus cereus. The antibacterial activity of synthesized compounds are compared with antibacterial activity of standard antibiotics cephalexine and streptomycine.   The compounds (1a,2a,3a) shows  different bacteriostatic and bacteriocidal activity.

Cyanoethylation and (Methoxycarbonyl)ethylation of Icosahedral ortho-Carborane Derivatives at Carbon Vertices via Michael Additions

2001 ◽  
Vol 66 (10) ◽  
pp. 1499-1507 ◽  
Author(s):  
Jaromír Plešek ◽  
Jaroslav Bačkovský ◽  
Jiří Fusek ◽  
Zbyněk Plzák
Keyword(s):  
Mass Spectrometry ◽  
Methyl Acrylate ◽  
Michael Addition ◽  
Nmr Spectra ◽  
Ammonium Hydroxide ◽  
Phase System ◽  
Melting Points ◽  
Two Phase ◽  
Michael Additions

The C-H vertices of ortho-carborane and its derivatives can be smoothly cyanoethylated with acrylonitrile in the presence of benzyl(triethyl)ammonium hydroxide in a two-phase system: dichloromethane/water or 1,2-dimethoxyethane/water. The reaction is highly specific and not transferable to its meta and para isomers. No Michael addition with methyl acrylate takes place under these conditions. However, with NaH as catalyst (methoxycarbonyl)ethylation can be accomplished with ortho-carborane; meta and para isomers react neither with acrylonitrile, nor with methyl acrylate even under such forcing conditions. The syntheses, properties and constitutions of 1-(2-cyanoethyl)-ortho-carborane, 1-(2-cyanoethyl)-2-phenyl-ortho-carborane, 1,2-bis(2-cyanoethyl)-ortho-carborane, 1-[2-(methoxycarbonyl)ethyl]-ortho-carborane and 1,2-bis[2-(methoxycarbonyl)ethyl]-ortho-carborane, along with their respective acids, are described. Melting points, TLC, "heated-inlet" mass spectrometry, and the 1H and 11B NMR spectra of all compounds, are presented. The scope of cyanoethylations and (methoxycarbonyl)ethylations of other deltahedral carbaboranes and heteroboranes is considered.

scholarly journals Synthesis and characterization of azetidin-2-one and 1,3-oxazepine derivatives using Schiff bases derived from 1,1’-biphenyl-4,4’-diamine

2021 ◽  
Vol 2063 (1) ◽  
pp. 012010
Author(s):  
H D Hanoon ◽  
H A Abd Al Hussain ◽  
S K Abass
Keyword(s):  
Schiff Bases ◽  
Heterocyclic Compounds ◽  
Nmr Spectra ◽  
Condensation Reaction ◽  
Synthesis And Characterization ◽  
Chloroacetyl Chloride ◽  
H Nmr ◽  
Ft Ir ◽  
Benzaldehyde Derivatives

Abstract The present study included the synthesis of two series of heterocyclic compounds, azetidin-2-one and 1,3-oxazepine derivatives. All synthesized compounds were characterized using FT-IR and 1H NMR spectra. The study was divided into two parts. The first synthesis Schiff bases derivatives (1-4) via the condensation reaction of 1,1′-biphenyl-4,4′-diamine (A) with benzaldehyde derivatives (2,5-dimethoxybenzaldehyde, 4-hydroxy-3-methoxybenzaldehyde, furan-2-carbaldehyde and 3-hydroxybenzaldehyde). The second synthesis azetidine-2-one derivatives (5-8) from the reaction of Schiff bases with chloroacetyl chloride. Schiff bases also reacted with maleic anhydride to yield 1,3-oxazepine derivatives (9-12).

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