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 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

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).

scholarly journals Thermodynamic Properties of Three Pyridine Carboxylic Acid Methyl Ester Isomers

2007 ◽  
Vol 52 (2) ◽  
pp. 580-585 ◽  
Author(s):  
Maria D. M. C. Ribeiro da Silva ◽  
Vera L. S. Freitas ◽  
Luís M. N. B. F. Santos ◽  
Michal Fulem ◽  
M. J. Sottomayor ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Methyl Ester ◽  
Thermodynamic Properties ◽  
Acid Methyl Ester ◽  
Pyridine Carboxylic Acid ◽  
Acid Methyl ◽  
Pyridine Carboxylic

Ruthenium-catalyzed Asymmetric Dehydrative Allylic Cyclization of Chalcogen 5-Membered Heteroaromatics

Synthesis ◽  
2021 ◽  
Author(s):  
Shinji Tanaka ◽  
Shoutaro Iwase ◽  
Sena Kanda ◽  
Marie Kato ◽  
Yutaro Kiriyama ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Bond Formation ◽  
Selection Method ◽  
Allylic Alcohol ◽  
Hydrogen Bond Formation ◽  
Pyridine Carboxylic Acid ◽  
Bicyclic Compounds ◽  
Allyl Complex ◽  
Pyridine Carboxylic ◽  
High Yields

The asymmetric dehydrative intramolecular allylation reactions of furan and thiophene were performed using a cationic cyclopentadienyl-ruthenium (CpRu) complex of a chiral pyridine carboxylic acid, namely Cl-Naph-PyCOOH. Both furan and thiophene tethered with an allylic alcohol gave the corresponding bicyclic compounds in high yields and enantioselectivities using 0.1–5 mol% of catalyst. The reaction was found to proceed via a similar enantioface selection method mechanism to that previously reported by our group, which involved halogen and hydrogen bond formation, in addition to the generation of an intermediate σ-allyl complex.

scholarly journals Crystal structure of (2R*,3aR*)-2-phenylsulfonyl-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b]isoxazole

2017 ◽  
Vol 73 (1) ◽  
pp. 85-87
Author(s):  
Yaiza Hernández ◽  
Isidro Marcos ◽  
Narciso M. Garrido ◽  
Francisca Sanz ◽  
David Diez
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Dipolar Cycloaddition ◽  
Vinyl Sulfone ◽  
Compound C ◽  
Phenyl Vinyl

The title compound, C12H15NO3S, was prepared by 1,3-dipolar cycloaddition of 3,4-dihydro-2H-pyrrole 1-oxide and phenyl vinyl sulfone. In the molecule, both fused five-membered rings display a twisted conformation. In the crystal, C—H...O hydrogen bonds link neighbouring molecules, forming chains running parallel to thebaxis.

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