A series of eight new ethyl ()-benzotriazolyl acrylates 6a-d and 7a-d have been synthesized by conventional heating and microwave irradiation from ethyl benzotriazolyl acetates 3 and 4 with the corresponding aromatic aldehydes. This work reports the synthetic approach and spectroscopic characterization (H, C-NMR, HRMS) of all the synthesized compounds. X-ray diffraction analyses were performed for molecules 6a, 7a and 7d. Photophysical properties of compounds were evaluated. Finally, compound 6a was tested in a human cell line and showed low to no cytotoxicity at relevant concentrations. Initial testing demonstrates its potential use as a fluid-phase fluorescent marker for live cell imaging.
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http://dx.doi.org/10.1039/c9ra00108e | DOI Listing |
Acta Crystallogr E Crystallogr Commun
October 2024
Institut für Organische Chemie Technische Universität Bergakademie, Freiberg, Leipziger Str 29 09599 Freiberg/Sachsen Germany.
In the crystal structure of the title compound, CHN, the tripodal mol-ecule exists in a conformation in which the substituents attached to the central arene ring are arranged in an alternating order above and below the ring plane. The three benzotriazolyl moieties are inclined at angles of 88.3 (1), 85.
View Article and Find Full Text PDFRSC Adv
March 2019
Department of Chemistry and Biochemistry, Brigham Young University 84602 Provo Utah USA +1 801 422 9416.
A series of eight new ethyl ()-benzotriazolyl acrylates 6a-d and 7a-d have been synthesized by conventional heating and microwave irradiation from ethyl benzotriazolyl acetates 3 and 4 with the corresponding aromatic aldehydes. This work reports the synthetic approach and spectroscopic characterization (H, C-NMR, HRMS) of all the synthesized compounds. X-ray diffraction analyses were performed for molecules 6a, 7a and 7d.
View Article and Find Full Text PDFChem Pharm Bull (Tokyo)
January 2007
Pharmaceutical Sciences, Fukuoka University, Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan.
The preparation of amide derivatives (4) by N-acylation of unprotected alpha-amino acids is easily achieved via readily available benzotriazolyl carboxylates (2a-d) or succinimidyl carboxylates (2e-f). These intermediates (2) are prepared from reaction of carboxylic acids (1) with 1-hydroxybenzotriazole (HO-Bt) or N-hydroxysuccinimide (HO-Su) in the presence of equimolar amounts of 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (WSCI). The overall yields of the target compounds (4) were excellent, and this two-stage procedure could be applicable as an alternative procedure for one-pot reaction.
View Article and Find Full Text PDFJ Org Chem
November 1997
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200.
A new general route to conjugated enynyl ketones was developed based on a two-step procedure. First, palladium-catalyzed cross-coupling reactions of 1-(benzotriazol-1-yl)propargyl ethyl ether (3) and vinyl triflates or vinyl bromides afforded the key intermediates [1-(benzotriazol-1-yl)-1-enynyl]methyl ethyl ethers 5a-d in good yields. Then reactions of compounds 5 with primary halides gave intermediates 8, which were hydrolyzed by dilute acid to enynyl ketones 9a-g.
View Article and Find Full Text PDFJ Org Chem
August 2001
Center for Heterocyclic Chemistry, Department of Chemistry, University of Florida, Gainesville, 32611-7200, USA.
1-[2-Arylthio(oxy)ethyl]-5-benzotriazolyl-2-pyrrolidinones 6a-e, 12 and 3-benzotriazolyl-2-[2-arylthio(oxy)ethyl]-1-isoindolinones 9a-f, 14 are readily available from reactions of benzotriazole (4), 2-(arylsulfanyl)ethylamines 3, or 2-phenoxyethylamine (11) with 2,5-dimethoxy-2,5-dihydrofuran (5) or 2-formylbenzoic acid (8). Lewis acid mediated cyclizations of 6 and 9 produced novel 1,4-benzothiazepines 7a-e and 10a-f, respectively. Cyclizations of 12 and 14 gave 1,4-benzoxazepines 13 and 15, respectively.
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