In the title compound, C15H14FNO3S2, the 2H-chromene ring system is close to being planar (r.m.s. deviation = 0.024 Å) and the morpholine ring adopts a chair conformation. The dihedral angle between the 2H-chromene ring system and the morpholine ring (all atoms) is 88.21 (11)°. In the crystal, inversion dimers linked by pairs of very weak C-H⋯F hydrogen bonds generate R 2 (2)(8) loops; C-H⋯O hydrogen bonds connect the dimers into [010] chains. Weak aromatic π-π stacking inter-actions between the pyran rings of the chromene systems [centroid-centroid distance = 3.6940 (16) Å] are also observed.
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http://dx.doi.org/10.1107/S2056989015021179 | DOI Listing |
Org Biomol Chem
July 2024
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati-781039, Assam, India.
The reactivity of 4-hydroxy-2-chromene-2-thione is investigated with aryl aldehydes and 5,5-dimethylcylohexane-1,3-dione (dimedone) in the presence of 20 mol% L-proline in toluene at 90 °C. Instead of the expected linear product with a sulphur atom in the ring provided by 4-hydroxydithiocoumarin or an angular product obtained from 4-hydroxycoumarin, the hitherto unreported products, 12-aryl substituted chromeno[2,3-]chromenes (4), were obtained in good to excellent yields. The reaction proceeds through a three-component reaction Knoevenagel condensation between dimedone with an aromatic aldehyde followed by Michael addition with 4-hydroxy-2-chromene-2-thione.
View Article and Find Full Text PDFPhys Chem Chem Phys
November 2023
Department of Applied Chemistry and Institute of Molecular Science, National Yang Ming Chiao-Tung University, Hsinchu 30010, Taiwan.
Nonadiabatic molecular dynamics simulations with a global switching algorithm have been performed at the TD-CAM-B3LYP-D3/def2-SVP level of theory for ultrafast photo-induced ring-opening and isomerization reactions upon S excitation for 2,2-diphenyl-2-chromene (DPC). Both DPC-T and DPC-C conformers undergo ring-opening relaxation and isomerization pathways accompanied with pyran conformation conserved and converted on the S or S states competition and cooperation between C-O bond dissociation and pyran inversion motions. Upon S excitation, the DPC-T mainly relaxes to the T-type conical intersection region and thus yields a higher ring-opening efficiency with a faster S decay and intermediate formation than those of the DPC-C mainly relaxing to C-type conical intersection.
View Article and Find Full Text PDFJ Org Chem
August 2023
Department of Chemistry and Chemical Sciences, Central University of Jammu, Rahya-Suchani (Bagla), District-Samba, Jammu 181143, Jammu and Kashmir, India.
An efficient, secondary amine-catalyzed cascade annulation of 2-/-propargylarylaldehydes with 2,6-dialkylphenols was established to access biologically relevant functionalized 2-chromenes and 1,2-dihydroquinolines tethered with a synthetically useful -quinone methide scaffold in high yields under microwave irradiation and conventional heating conditions. The microwave-assisted strategy was convenient, clean, rapid, and high yielding in which the reactions were completed in just 15 min, and the yields obtained were up to 95%. This highly atom-economical domino process constructed two new C-C double bonds and a six-membered O/N-heterocyclic ring in a single synthetic operation.
View Article and Find Full Text PDFMolecules
December 2022
Institute of Natural Sciences and Mathematics, Ural Federal University, 51 Lenina Ave., 620000 Ekaterinburg, Russia.
The AgOAc-catalysed reaction of 3-nitro-2-phenyl-2-chromenes with stabilized azomethine ylides generated from the imines based on methyl glycinate and arylaldehydes leads to a mixture of and ' isomers of the corresponding chromeno[3,4-]pyrrolidines in a ratio of 2.0-2.3:1 in 85-93% total yields as a result of a Michael addition/Mannich reaction sequence.
View Article and Find Full Text PDFMolecules
October 2022
Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdansk, Poland.
A series of copper(II) complexes of 2-imino-2-chromen-3-yl-1,3,5-triazines , 3-(benzoxazol-2-yl)-2-chromen-2-imines , and 3-(benzothiazol-2-yl)-2-chromen-2-imines were obtained by reacting of appropriate 2-iminocoumarin ligands , , and with 3-fold molar excess of copper(II) chloride. The structure of these compounds was confirmed by IR spectroscopy, elemental analysis, and single-crystal X-ray diffraction data (, , , and ). All the synthesized complexes were screened for their activity against five human cancer cell lines: DAN-G, A-427, LCLC-103H, SISO, and RT-4 by using a crystal violet microtiter plate assay and relationships between structure and in vitro cytotoxic activity are discussed.
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