scholarly journals Synthesis and reactions of [1]benzofuro[3,2-c]pyridine

2022 ◽  
Vol 7 (1) ◽  
pp. 107-114
Author(s):  
Nadežda Juristová ◽  
Eleonóra Štefanovová ◽  
Tatiana Ďurčeková ◽  
Naďa Prónayová ◽  
Anton Gatial ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Title Compound ◽  
Benzoyl Chloride ◽  
Phosphorus Oxychloride ◽  
Diphenyl Ether ◽  
Potassium Cyanide ◽  
Complex Compounds ◽  
Propenoic Acid

(E)-3-(1-Benzofuran-2-yl)propenoic acid (I) was prepared from 1-benzofuran-2-carbaldehyde under the Doebner’s conditions. The obtained acid was converted to the corresponding azide II, which was cyclized by heating in diphenyl ether to [1]benzofuro[3,2-c]pyridin-1(2H)-one (III). This compound was aromatized with phosphorus oxychloride to chloroderivative IV which was reduced with zinc and acetic acid to the title compound V. [1]Benzofuro[3,2-c]pyridin-2-oxide (VI) was synthesized by reaction of V with 3-chloroperoxybenzoic acid in dichloromethane. Treatment VI with benzoyl chloride and potassium cyanide (Reissert-Henze reaction) was shown to produce the corresponding [1]benzofuro[3,2-c]pyridin-1-carbonitrile (VII). The title compound was used for preparation of complex compounds VIII, IX

Synthesis and reactions of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine

2008 ◽  
Vol 62 (4) ◽  
Author(s):  
Ivana Bradiaková ◽  
Naďa Prónayová ◽  
Anton Gatial ◽  
Alžbeta Krutošíková
Keyword(s):  
Title Compound ◽  
Benzoyl Chloride ◽  
Phosphorus Oxychloride ◽  
Diphenyl Ether ◽  
Potassium Cyanide ◽  
Dipolar Cycloaddition ◽  
Pyridine Carboxylic Acid ◽  
Propenoic Acid ◽  
Pyridine Carboxylic ◽  
Acid Esters

Abstract(E)-3-{5-[3-(Trifluoromethyl)phenyl]furan-2-yl}propenoic acid (I) was prepared from 5-[3-(tri-fluoromethyl)phenyl]furan-2-carbaldehyde under the Doebner’s conditions. The obtained acid was converted to the corresponding azide II, which was cyclized by heating in diphenyl ether to 2-[3-(trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one (III). This compound was aromatized with phosphorus oxychloride to chloroderivative IV which was reduced with H2NNH2-Pd/C to the title compound V. 2-[3-(Trifluoromethyl)phenyl]furo[3,2-c]pyridin-5-oxide (VI) was synthesized by reaction of V with 3-chloroperoxybenzoic acid in dichloromethane. On treatment of VI with benzoyl chloride and potassium cyanide (Reissert-Henze reaction), corresponding 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine-1-carbonitrile (VII) resulted. 5-Amino-2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridin-5-ium-4-methylbenzene sulfonate (VIII) was prepared by direct N-amination of the title compound V with 1-[(aminooxy)sulfonyl]-4-methylbenzene in dichloromethane. Then, VIII was transformed to a non-isolated zwitterionic N-imid IX which afforded the corresponding furo[3,2-c]pyrazolo[1,5-a]pyridine carboxylic acid esters X, XI by 1,3-dipolar cycloaddition reactions with dimethyl but-2-ynedionate (DBD) or ethyl propiolate. The structures of all compounds were confirmed by their IR and NMR spectra.

scholarly journals Synthesis, Complex Compounds and Antimicrobial Activity of Some Derivatives of Furo[3,2-C]Pyridine and Their Starting Compounds

2012 ◽  
Vol 11 (1) ◽  
pp. 73-85
Author(s):  
Martin Hrašna ◽  
Eva Ürgeová ◽  
Alžbeta Krutošíková
Keyword(s):  
Antimicrobial Activity ◽  
Boronic Acid ◽  
Erwinia Amylovora ◽  
Phosphorus Oxychloride ◽  
Coupling Reaction ◽  
Complex Compounds ◽  
Suzuki Coupling Reaction ◽  
Propenoic Acid ◽  
Unexpected Product ◽  
Derivatives Of

Synthesis, Complex Compounds and Antimicrobial Activity of Some Derivatives of Furo[3,2-C]Pyridine and Their Starting CompoundsSome [3,2-c]pyridine derivatives were synthesized. 3-(Furan-2-yl)propenoic acid (1a) was prepared from furan-2-carbaldehyde under the Perkin's conditions. Obtained acid was converted to the corresponding azide3, which in turn was cyclized to give furo[3,2-c]pyridin-4(5H)-one (4a). The reaction of pyridone4awith phosphorus oxychloride rendered the chloroderivative7a, which was treated in the condition of Suzuki coupling reaction with boronic acid to give 4-phenylfuro[3,2-c]pyridine (8e) and an unexpected product10. Some title compounds have shown moderate to good antimicrobial activity against tested bacteriaXanthomonas sp., Erwinia amylovora, and filamentous fungiPyrenophora avenae, Fusarium graminearum.

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.

Analysis of Bioactive Chemical Compounds of Trogoderma granarium (Insecta: Coleoptera: Dermestidae) Using Gas Chromatography – Mass Spectrometry

2017 ◽  
Vol 9 (03) ◽  
Author(s):  
Jenan Mohammed Ubaid ◽  
Abeer Fauzi Al-Rubaye ◽  
Imad Hadi Hameed
Keyword(s):  
Acetic Acid ◽  
Benzoyl Chloride ◽  
Methanolic Extract ◽  
Biological Activities ◽  
Chemical Compounds ◽  
Gas Chromatography Mass Spectrometry ◽  
Pentanoic Acid ◽  
Trogoderma Granarium ◽  
Trans Methyl ◽  
Phenacyl Thiocyanate

Methanolic extract of bioactive compounds of Trogoderma granarium was assayed. GC-MS analysis of Trogoderma granarium revealed the existence of the Pentanoic acid , 1,1-dimethylpropyl ester , (1H)-Pyrimidinone , 5-chloro-4,6- diphenyl, Cyclobutanemethanol , α-methyl- , Nitro-2-methyl-1,3-propanediol , Hydroxylamine ,O-(2-methylpropyl)- , Uridine , 2',3'-O-(phenylmethylene)- ,Acetic acid ,2-benzoylthio-,2-oxo-2-phenylethyl ester , methylpropyl)- , Uridine , 2',3'-O-(phenylmethylene)- , 5'-(4-methylbenzenesulfo , Indolinol , 1-benzoyl-, Benzeneethanol , β-methyl-,(s)- , Acetic acid ,2-benzoylthio-,2-oxo-2-phenylethyl ester , Phenacyl thiocyanate , Deoxy-L-ribose-2,5-dibenzoate , Methenamine , Alanine , N-methyl-n-propargyloxycarbonyl-, decyl ester , Benzoyl chloride , Thiophene-2-ol , benzoate , Ethanone , -(5- nitrotetrazol-2-yl)-1-phenyl- , 2,5-Dimethylhexane-2,5-dihydroperoxide , Benzamide , N-(3-benzylthio-1,2,4-thiadiazol- 5-yl)- , Methyl p-(2-phenyl-1-benzimidazolyl)benzoate , Methyl-2-phenoxyethylamine , Pentaborane(11) , cis-Methoxy- 5-trans-methyl-1R-cyclohexanol , Nitro-1-phenyl-3-(tetrahydropyran-2-yloxy)propan-1-one , cis-Methoxy-5-transmethyl-1R-cyclohexanol. Trogoderma granarium produce many important secondary metabolites with high biological activities.

Fluorinated analogues of tricyclic neuroleptics: 6,9-difluoro derivative of 10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1980 ◽  
Vol 45 (10) ◽  
pp. 2688-2694 ◽  
Author(s):  
Irena Červená ◽  
Marta Hrubantová ◽  
Emil Svátek ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Title Compound ◽  
Substitution Reaction ◽  
Polyphosphoric Acid ◽  
Satisfactory Yield ◽  
Chloro Derivative ◽  
Cns Activity

The acid VI, obtained from 2,5-difluorothiophenol (IV) and (2-iodophenyl)acetic acid, afforded by cyclization with polyphosphoric acid 6,9-difluorodibenzo[b,f]thiepin-10(11H)-one (VII) in a satisfactory yield. Two further steps led to the chloro derivative X giving by a substitution reaction with 1-methylpiperazine the title compound III. This substance exhibits some 10% incoordinating activity of the unsubstituted compound I and an indication of cataleptic activity, in contrast to the inactive analogous dichloro compound II. The bulky atom of chlorine in the vicinity of the methylpiperazine residue interferes evidently with the CNS activity; the influence of the atom of fluorine is much less pronounced in this line.

scholarly journals N-(5-Chloro-1,3-thiazol-2-yl)-2,4-difluorobenzamide

2012 ◽  
Vol 68 (6) ◽  
pp. o1857-o1857 ◽  
Author(s):  
Xi-Wang Liu ◽  
Jian-Yong Li ◽  
Han Zhang ◽  
Ya-Jun Yang ◽  
Ji-Yu Zhang
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Dihedral Angle ◽  
Title Compound ◽  
Benzoyl Chloride ◽  
Bond Lengths ◽  
Compound C

The title compound, C10H5ClF2N2OS, was obtained by linking an amino heterocycle and a substituted benzoyl chloride. The dihedral angle between the two rings is 41.2 (2)° and the equalization of the amide C—N bond lengths reveals the existence of conjugation between the benzene ring and the thiazole unit. In the crystal, pairs of N—H...N hydrogen bonds link molecules into inversion dimers. Non-classical C—H...F and C—H...O hydrogen bonds stabilize the crystal structure.

scholarly journals 2-Aminocyclohexan-1-aminium thiocyanate

2012 ◽  
Vol 68 (6) ◽  
pp. o1732-o1732 ◽  
Author(s):  
Halima F. Salem ◽  
Siti Aishah Hasbullah ◽  
Bohari M. Yamin
Keyword(s):  
Title Compound ◽  
Benzoyl Chloride ◽  
Ammonium Thiocyanate ◽  
Chair Conformation ◽  
Cyclohexane Ring ◽  
Two Dimensional ◽  
Thiocyanate Anion ◽  
Compound C

The title compound, C6H15N2 +·NCS−, was obtained unexpectedly from the reaction mixture of benzoyl chloride, ammonium thiocyanate and cyclohexane-1,2-diamine. The cyclohexane ring adopts a chair conformation. In the crystal, N—H...S and N—H...N interactions involving the thiocyanate anion and both the amine and the aminium N atoms link the molecules, forming two-dimensional networks parallel to (001).

Systhesis, Characterization and Spectroscopic Properties of (2E,6E)-2,6-Bis(2,3,4-tri-methoxy-benzylidene)cyclohexanone

2011 ◽  
Vol 396-398 ◽  
pp. 2338-2341
Author(s):  
Xing Chuan Wei ◽  
Zhi Li Liu ◽  
Kun Zhang ◽  
Zhi Yun Du ◽  
Xi Zheng
Keyword(s):  
Crystal Structure ◽  
Acetic Acid ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Spectroscopic Properties ◽  
Spectral Studies ◽  
Double Bonds ◽  
X Ray ◽  
Π Interactions ◽  
X Ray Crystallography

In this paper, (2E,6E)-2,6-Bis(2,3,4-tri-methoxy -benzylidene)cyclohexanone (omitted as tmbcho) (1) was obtained by the reaction of acetic acid, tetrahydrofuran, cyclohexanone and 2,3,4-tri-methoxy-benzaldehyde. Three non-classic hydrogen bonds were observed in the compound. X-ray crystallography shows that the crystal structure is stabilized by intermolecular C-H•••π interactions and it contains plenty of conjugated double bonds. The title compound was characterized by UV-vis and fluorescent spectral studies.

scholarly journals 6-[1-Acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-3-yl]-2(3H)-benzoxazolone

Molbank ◽  
10.3390/m1021 ◽  
2018 ◽  
Vol 2018 (4) ◽  
pp. M1021
Author(s):  
Yordanka Ivanova ◽  
Antonya Todorova ◽  
Christo Chanev ◽  
Ognyan Petrov
Keyword(s):  
Acetic Acid ◽  
Hydrazine Hydrate ◽  
1H Nmr ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Title Compound ◽  
Target Compound

The title compound, 6-[1-acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2(3H)-benzoxazolone, was synthesized by condensation of 6-[3-(4-methoxyphenyl)-2-propenoyl]-2(3H)-benzoxazolone (1) and hydrazine hydrate in acetic acid in 84% yield. The structure of the target compound was confirmed using 1H-NMR, 13C-NMR, IR, MS, and elemental analysis.

The Meisenheimer rearrangement in heterocyclic synthesis. II. Synthesis and X-ray crystal structure of a tetrahydro-1H-2,3-benzoxazocine and preparation of a hexahydro-2,3-benzoxazonine

1980 ◽  
Vol 33 (6) ◽  
pp. 1323 ◽  
Author(s):  
JB Bremner ◽  
EJ Browne ◽  
PE Davies ◽  
CLWAH Raston
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Acetic Acid ◽  
Crystal And Molecular Structure ◽  
Phosphorus Oxychloride ◽  
Crystallographic Analysis ◽  
Heterocyclic Synthesis ◽  
Reaction Conditions ◽  
X Ray ◽  
Heterocyclic Derivatives

The heterocyclic derivatives, 8,9-dimethoxy-3-methyl-1-phenyl-3,4,5,6- tetrahydro-1H-2,3-benzoxazocine(3a) and 9,10-dimethoxy-3-methyl-1- phenyl-1,3,4,5,6,7-hexahydro-2,3-benzoxazonine (3b),examples of two new ring systems, have been prepared by Meisenheimer rearrangement of the corresponding 2-benzazepine and 2-benzazocine N-oxide derivatives (2a) and (2b). The Bischler-Napieralski-type cyclization reaction was used in the preparation of the tertiary amine precursors of these N-oxides reaction conditions for the cyclization were critical and phosphorus oxychloride in refluxing butanenitrile was found to give the best yields of the seven- or eight-membered cyclic imine intermediates. Reductive cleavage of the benzoxazocine derivative (3a) with zinc in acetic acid followed by N-methylation gave the expected product, [2-{3- (dimethylamino)propyl}-4,5-di-methoxyphenyl]phenylmethanol (12). The crystal and molecular structure of (3a) has been determined by X-ray crystallographic analysis.

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