New Pyrrolo[1,2-b]pyridazine Derivatives by 1,3-Dipolar Cycloaddition of Mesoionic Oxazolopyridazinone

2008 ◽  
Vol 59 (11) ◽  
Author(s):  
Miron Teodor Caproiu ◽  
Florea Dumitrascu ◽  
Mino R. Caira
Keyword(s):  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Pyridazine Derivatives ◽  
New Compounds

New pyrrolo[1,2-b]pyridazine derivatives 8a-f were synthesized by 1,3-dipolar cycloaddition reaction between mesoionic 1,3-oxazolo[3,2-b]pyridazinium-2-oxides and diethyl or diisopropyl acetylenedicarboxylate as alkyne dipolarophiles. The structures of the new compounds were assigned by elemental analysis and NMR spectroscopy.

scholarly journals Synthesis, characterization and acute toxicity of new Schiff base derived from phenylethyl amine and 2-hydroxy naphthaldehyde

2019 ◽  
Vol 10 (1) ◽  
pp. 26-29
Author(s):  
Ibtihal Hassan Hatim ◽  
Wasfi Aboud Al-Masoudi ◽  
Rashad Fadhil Ghadhban
Keyword(s):  
Body Weight ◽  
Schiff Base ◽  
Nmr Spectroscopy ◽  
Acute Toxicity ◽  
Elemental Analysis ◽  
Good Yield ◽  
Mice Model ◽  
Base Derivative ◽  
New Compounds

There is an urgent need for the design and development of new and safer drugs, this has attracted organic chemists to synthesize new compounds with potential of biological and chemotherapeutic activities. Here we report, the condensation of phenylethylamine with 2-hydroxy naphthaldehyde yielded Schiff base derivative in good yield. Characterization of synthesized compound was carried by elemental analysis, IR, 1H-, 13C- and HSQC-NMR spectroscopy. The toxicity of the synthesized compound was determined using Balb/c mice model. Dixon’s up and down method was found to have an LD50 of 827.2 mg/kg of body weight, moderate toxicity.

scholarly journals Synthesis of cis, cis-1,3,5-trisubstituted cyclohexane based chelators with polyfunctional pendant arms

2005 ◽  
Vol 2005 (1) ◽  
pp. 43-45 ◽  
Author(s):  
Minati Baral ◽  
B.K. Kanungo ◽  
Peter Moore
Keyword(s):  
Schiff Base ◽  
Nmr Spectroscopy ◽  
Organic Compounds ◽  
Elemental Analysis ◽  
H Nmr ◽  
Benzenetricarboxylic Acid ◽  
New Compounds ◽  
Pendant Arms ◽  
C Nmr

Some novel organic compounds of the type: cis, cis-1,3,5-tris(X)cyclohexane, where X= –CONH(CH2)2NH2, –CONH(CH2)3NH2, –CONH(CH2)2NCH –C6H4OH, CONH(CH2)3NCHC6H4OH, which are expected to function as potential polydentate chelators have been synthesised from 1,3,5-benzenetricarboxylic acid through multi-steps reactions. 1,3,5-benzenetricarboxylic acid was reduced to cis, cis-1,3,5-tris(ethylcarboxylate)cyclohexane, which on reaction with excess of 1,2-diaminoethane and 1,2-diaminopropane afforded two new compounds. Condensation of the obtained derivatives with three equivalents of salicylaldehyde resulted the formation of two new Schiff base compounds. All the compounds were characterised by a combination of elemental analysis, mass, IR, UV-Vis, 1H NMR and 13C NMR spectroscopy.

New Heterocyclic Compounds from 1,2,4-triazoles Class with Potential Cytotoxic Activity

2017 ◽  
Vol 68 (11) ◽  
pp. 2503-2508 ◽  
Author(s):  
Laura Ileana Socea ◽  
Stefania Felicia Barbuceanu ◽  
Bogdan Socea ◽  
Constantin Draghici ◽  
Theodora Venera Apostol ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Cytotoxic Activity ◽  
Spectral Data ◽  
1H Nmr ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Heterocyclic Compounds ◽  
Cytotoxic Effect ◽  
13C Nmr Spectroscopy ◽  
New Compounds

Acylhydrazinecarbothioamides (2a,b) were synthesized by addition of 2-(5H-dibenzo[a,d][7]annulen-5-yl)acetohydrazide to different isothiocyanates. The new 1,2,4-triazol-3-thioles (3a,b) were synthesized by cyclization of new 2- acylhydrazinecarbothioamides (3a,b) in basic media. Alkylation of 1,2,4-triazole-3-thiols (3a-c) with ethyl bromide gave only S-substituted derivatives (4a-c). The structures of the synthesized compounds have been established on spectral data (IR, 1H-NMR and 13C-NMR spectroscopy) and elemental analysis. The cytotoxic effect of new compounds was evaluated using two alternative models on plant and invertebrate organisms.

Synthesis and In Vitro Anti-Ulcer Effect of Triazolo-Methyl Tetrahydrobenzofuran Oxime Ether Derivatives

2013 ◽  
Vol 746 ◽  
pp. 35-39 ◽  
Author(s):  
Hu Biao Fang ◽  
Lei Jin ◽  
Cheng Qiao Cao ◽  
Hua Jun Luo ◽  
Nian Yu Huang
Keyword(s):  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
Inhibitory Effect ◽  
Dipolar Cycloaddition ◽  
Reaction Sequence ◽  
Oxime Ether ◽  
Esi Ms ◽  
Mild Conditions ◽  
Activity Evaluation

The triazolo-methyl tetrahydrobenzofuran oxime ether isomers were prepared through Cu (II)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction in a high-yielding three-step reaction sequence under mild conditions. All of the intermediates and target compounds were characterized by NMR, IR, ESI-MS and elemental analysis. Thein vitroanti-ulcer activity evaluation indicated the (Z)-oxime isomer of triazolo-methyl tetrahydrobenzofuran oxime ether exhibited most potent H+/K+-ATPase inhibitory effect with the IC50˰̵̱̼͆ͅ˰̶̿˰̅˾́̅˰μ̝˾ These compounds could be potentially used as anti-ulcer agents for the treatment of acid related diseases.

scholarly journals Synthesis of 1-(2-Fluorophenyl)pyrazoles by 1,3-Dipolar Cycloaddition of the Corresponding Sydnones

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3693
Author(s):  
Denisa Dumitrescu ◽  
Sergiu Shova ◽  
Constantin Draghici ◽  
Marcel Mirel Popa ◽  
Florea Dumitrascu
Keyword(s):  
Crystal Structure ◽  
Nmr Spectroscopy ◽  
Cycloaddition Reaction ◽  
Halogen Bonding ◽  
Dipolar Cycloaddition ◽  
Dimethyl Acetylenedicarboxylate ◽  
Reaction Intermediates ◽  
X Ray Diffraction ◽  
X Ray ◽  
Important Interaction

3-Arylsydnones bearing fluorine and bromine atoms on the benzene ring were synthesized from N-nitroso-2-fluorophenylglycines and characterized by NMR spectroscopy. These were employed further in synthesis of the corresponding 1-(2-fluorophenyl)pyrazoles by 1,3-dipolar cycloaddition reaction with dimethyl acetylenedicarboxylate (DMAD) as activated dipolarophile. The sydnones as reaction intermediates were characterized by single crystal X-ray diffraction analysis showing interesting features such as halogen bonding as an important interaction in modeling the crystal structure.

New Substituted Indolizines by 1,3-Dipolar Cycloaddition Reactions I. 7-tert-Butylindolizines

2008 ◽  
Vol 59 (3) ◽  
pp. 269-272
Author(s):  
Emilian Georgescu ◽  
Florentina Georgescu ◽  
Constantin Draghici ◽  
Petru Filip ◽  
Florea Dumitrascu
Keyword(s):  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Tert Butyl ◽  
Butyl Group ◽  
Tert Butyl Group

The new indolizine derivatives 6a-h containing a tert-butyl group grafted on the pyridinic ring were obtained by reaction of N-phenacylpyridinium bromides 3 with ethyl propiolate as acetylenic dipolarophile in medium of 1,2-epoxybutane at reflux. Structural proof for the compounds was provided by elemental analysis and NMR spectroscopy, including COSY and HETCOR experiments.

scholarly journals Diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate

Molbank ◽  
10.3390/m1167 ◽  
2020 ◽  
Vol 2020 (4) ◽  
pp. M1167
Author(s):  
Serigne Abdou Khadir Fall ◽  
Saïd Achamlale ◽  
Younas Aouine ◽  
Asmae Nakkabi ◽  
Hassane Faraj ◽  
...  
Keyword(s):  
Infrared Spectroscopy ◽  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
2D Nmr ◽  
Solvent Mixture ◽  
Sodium Ascorbate ◽  
Dipolar Cycloaddition ◽  
Sulfate Pentahydrate ◽  
Copper Sulfate Pentahydrate

The title compound, diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate, was synthesized with excellent yield and high regioselectivity through 1,3-dipolar cycloaddition reaction between the α-azido diethyl amino methylphosphonate and the heterocyclic alkyne, 9-(prop-2-yn-1-yl)-9H-carbazole. The cyclization reaction by “click chemistry” was carried out in a water/ethanol solvent mixture (50/50), in the presence of copper sulfate pentahydrate and catalytic sodium ascorbate. The characterization of the structure of the resulting 1,4-regioisomer was performed by 1D and 2D-NMR experiments, infrared spectroscopy, and elemental analysis.

Kondensationsreaktionen von Trifluornitrosomethan CF3NO mit Sulfanilamid H2NC6H4SO2NH2-Darstellung von CF3NNC6H4SO2NH2, CF3NNC6H4SO2NNCF3, CH3C(O)N(H)C6H4SO2NNCF3 und CF3C(0)N (H)C6H4SO2NH2 / Condensation Reactions of Trifluoronitrosomethane CF3NO with Sulfanilamide H2NC6H4SO2NH2- Preparation of CF3NNC6H4SO2NH2, CF3NNC6H4SO2NNCF3, CH3C(0)N(H)C6H4SO2NNCF3 and CF3C(0)N (H)C6H4SO2NH2

1997 ◽  
Vol 52 (5) ◽  
pp. 647-654 ◽  
Author(s):  
Rolf Minkwitz ◽  
Jens Jakob ◽  
Andreas Winter
Keyword(s):  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Protecting Groups ◽  
Amino Group ◽  
Condensation Reactions ◽  
New Compounds ◽  
C Nmr

Abstract We report the condensations of trifluoronitrosom ethane with sulfanilamide. The new compounds p-trifluorom ethylazophenylsulfonamide CF3NNC6H4SO2NH2, p-trifluorom ethylazosulfonyltrifluorom ethylazobenzole CF3NNC6H4SO2NNCF3 and p-trifluoromethylazosulfonylacetanilide CH3C(O)N(H)C6H4SO2NNCF3 were characterized by elemental analysis, IR, Raman, mass, 1H , 19F and 13C NMR spectroscopy. In addition we present our approach to the preparation of p-trifluorom ethylazosulfonylaniline H2NC6H 4SO2NNCF3 by using protecting groups for the amino group.

Synthesis and Structural Characterization of Metal Complexes of 2-Formylpyrrole 4N-Methylthiosemicarbazone (4ML1) and 2-Acetyl- pyrrole 4N-Methylthiosemicarbazone (4ML2). The X-Ray Crystal Structures of [Ni(4ML1-H)2], [Pd(4ML1-H)2] and [Cd(4ML2)2I2]

2001 ◽  
Vol 56 (3) ◽  
pp. 219-228 ◽  
Author(s):  
Ruben Alonso ◽  
Elena Bermejo ◽  
Rosa Carballo ◽  
Alfonso astiñeiras ◽  
Teresa Pérez
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Structural Characterization ◽  
X Ray ◽  
Group 12 ◽  
New Compounds ◽  
Group 10 Metals ◽  
C Nmr

Abstract Reaction of 4N-methyl-2-[1-(pyrrol-2-yl)methylidene]hydrazinecarbothioamide (4ML1 and 4N-methyl-2-[1-(pyrrol-2-yl)-ethylidene]hydrazine carbothioamide (4ML1) with zinc(II), cadmium(II) and mercury(II) halides afforded complexes with formulas [M(L)X2] [(L; M; X) =(4ML1; Cd; Cl) (4), (4ML1; Hg; Cl, Br, I) (7 - 9), (4ML2; Cd; Cl) (17), (4ML2; Hg; Cl, Br, I) (20 - 22)] or [M(L)2X2] [(L; M; X) = (4ML1; Zn; Cl, Br, I) (1 - 3), (4ML1; Cd; Br, I) (5, 6), (4ML2; Zn; Cl, Br, I) (14 - 16), (4ML2; Cd; Br, I) (18, 19)]. Reaction of 4ML1 with salts of copper(II), nickel(II), palladium(II) and platinum(II) afforded complexes of formula [M(4ML1-H)2] (10 -13). Crystals of 11, 12 and 19 were studied by X-ray diffractometry, and all new compounds were characterized by elemental analysis, mass spectrometry, and IR, electronic and 1H and 13C NMR spectroscopy and, when pertinent and allowed by the solubility of the compound, 113Cd or 199Hg NMR spectroscopy. In the complexes of Group 12 metals, both ligands are neutral and S-monodentate. In the complexes of copper or Group 10 metals, 4ML1 is monodeprotonated and S,N-bidentate.

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