Synthesis and structure of dithiocarbonimidates derived from aromatic heterocycles: Role of weak interactions in the preferred conformation

Peña-Hueso, Adrián; Téllez, Fabiola; Vieto-Peña, Rebeca; Esquivel, Rodolfo O.; Esparza‐Ruiz, Adriana; Ramos-Garcı́a, Iris; Contreras, Rosalinda; Barba-Behrens, Noráh; Flores‐Parra, Angelina

doi:10.1016/j.molstruc.2010.10.016

Cited by 10 publications

(3 citation statements)

References 53 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction between 2-amino-5-choloro-benzoxazole and carbon disulfide CS 2 in the presence of a strong base gives dimethyl-5-chloro-1,3-benzoxazol-2-yl-dithiocarboimidate (2). [17] Compound 2 by reaction with o-aminophenol afforded ligand 1 (Scheme 1). Three crystals of compound 1 were obtained and analyzed by X-ray diffraction.…”

Section: Resultsmentioning

confidence: 99%

“…Dimethyl-5-chloro-1,3-benzoxazol-2-yl-dithiocarboimidate (2) was prepared from 2-amino-5-chloro-benzoxazole, CS 2 , and NaOH, as reported. [17] A solution of compound 2, (2.72 g,10 mmol in 15 mL of DMF) was added dropwise to a solution of o-aminophenol (1.10 g, 10 mmol) in DMF (25 mL) and NaOH(aq) (0.4 g,10 mmol).-The mixture was stirred at room temperature for 0.5 h and refluxed for 4 h. After cooling, the mixture was poured into water (300 mL) and neutralized with concentrated HCl. The precipitate was filtered, washed with water, dried in vacuo and crystallized from methanol.…”

Section: Synthesis Of [(13-benzoxazol-2-yl)-(5-chloro-13-benzoxazol-2...mentioning

confidence: 99%

See 1 more Smart Citation

Structural Analysis and Coordination Compounds of [(1,3‐Benzoxazol‐2‐yl)‐(5‐chloro‐1,3‐benzoxazol‐2‐yl)]amine

Téllez¹,

Ramírez-Trejo²,

Vieto-Peña³

et al. 2013

Zeitschrift anorg allge chemie

Self Cite

View full text Add to dashboard Cite

A novel [(1,3-benzoxazol-2-yl)-(5-chloro-1,3-benzoxazol-2yl)]amine (L) (1) compound was synthesized. The molecule has a nitrogen atom between 1,3-benzoxazol-2-yl and 5-chloro-1,3-benzoxazol-2-yl groups. For compound 1 there are twelve possible conformers and tautomers. Ab initio calculations were performed in order to investigate the more stable structures. Three crystals of compound Materials and Methods: All chemicals were reagent grade: methanol (J. T. Baker), 2-amino-5-chloro-benzoxazole (Aldrich); NaOH, CS 2 , CH 3 I, DMF, THF, Co(CH 3 CO 2 ) 2 ·4H 2 O, and Ni(CH 3 CO 2 ) 2 ·4H 2 O. They were used without further purification. Melting points were determined with an Electrothermal 9100 apparatus. FAB mass spectra were obtained with a Jeol model SX-102 spectrometer. Elemental analyses were carried out with a Fisions Instruments EA-1108. An FT IR spectrometer (Perkin-Elmer Model 1605) was used for obtaining IR spectra of solid samples in KBr pellets (4000-400 cm -1 ). The UV/ Vis/NIR spectra (diffuse reflectance) were recorded with a Varian Cary 5E spectrophotometer. NMR spectra were recorded with a VARIAN model Unity Inova (300 and 400 MHz) or a Bruker-Avance-DPX 300 by using [D 6 ]DMSO or CDCl 3 as solvent. Magnetic susceptibility measurements were performed on pulverized samples at room temperature with a Johnson Matthey DG8 5HJ balance. X-ray single crystal data for 1a, 1b, and1c were collected with a KAPPA-CCD area detector diffractometer. The crystal structures were determined and refined with the SHELXS97 and Crystals programs. [18,19] Ab initio cal-[(1,3-Benzoxazol-2-yl)-(5-chloro-1,3-benzoxazol-2-yl)]amine culations were performed in order to obtain the minimum energy structure for the twelve tautomers and conformers of compound 1 using the Gaussian 98 package. [20] Geometries were checked to be the minimal by means of the frequency analysis.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of [(13-benzoxazol-2-yl)-(5-chloro-13-benzoxazol-2...mentioning

confidence: 99%

Structural Analysis and Coordination Compounds of [(1,3‐Benzoxazol‐2‐yl)‐(5‐chloro‐1,3‐benzoxazol‐2‐yl)]amine

Téllez¹,

Ramírez-Trejo²,

Vieto-Peña³

et al. 2013

Zeitschrift anorg allge chemie

Self Cite

View full text Add to dashboard Cite

show abstract

“…After neutralization of 14 with one equivalent of NaOH, (15) was obtained quantitatively as a white solid. This compound has already been obtained from 1-methyl-2-aminobenzimidazole whose NMR data and X-ray diffraction structure has been reported elsewhere [16].…”

Section: Scheme 2 Methylation Reactions Of 2-aminobenzimidazole (3)mentioning

confidence: 99%

Synthesis and Structure of Sulfur Derivatives from 2-Aminobenzimidazole

et al. 2014

View full text Add to dashboard Cite

Abstract:The reactions of the benzimidazole nitrogen atoms and the exocyclic amino group of 2-aminobenzimidazole with CS2 in NaOH basic medium followed by methylation with methyl iodide was explored. With careful control of the stoichiometric quantities and addition sequences, this set of reactions allows the selective functionalization of the benzimidazole ring with N-dithiocarbamate, S-methyldithiocarbamate or dimethyldithiocarboimidate groups. The products were characterized by 1 H-, 13 C-NMR spectroscopy and three of them by X-ray diffraction analysis. The preferred isomers, tautomers and conformers were established.

show abstract

Reaction of Enamines and Azaenamines Containing a Thioamide Group with Dimethyl Acetylenedicarboxylate

Belskaya

Lugovik

Ivina

et al. 2014

Chem Heterocycl Comp

View full text Add to dashboard Cite

Synthesis and structure of dithiocarbonimidates derived from aromatic heterocycles: Role of weak interactions in the preferred conformation

Cited by 10 publications

References 53 publications

Structural Analysis and Coordination Compounds of [(1,3‐Benzoxazol‐2‐yl)‐(5‐chloro‐1,3‐benzoxazol‐2‐yl)]amine

Structural Analysis and Coordination Compounds of [(1,3‐Benzoxazol‐2‐yl)‐(5‐chloro‐1,3‐benzoxazol‐2‐yl)]amine

Synthesis and Structure of Sulfur Derivatives from 2-Aminobenzimidazole

Reaction of Enamines and Azaenamines Containing a Thioamide Group with Dimethyl Acetylenedicarboxylate

Contact Info

Product

Resources

About