5662-03-3Relevant articles and documents
Tautomeric preferences of phthalones and related compounds
Dobosz, Robert,Kolehmainen, Erkki,Valkonen, Arto,O?mia?owski, Borys,Gawinecki, Ryszard
, p. 9172 - 9178 (2007)
Multinuclear magnetic resonance and IR spectra prove that although 2-(diacylmethyl)pyridines and 2-(diacylmethyl)quinolines are β-diketones, their proton transfer product present in chloroform solution is not ketoenol but enaminone (earlier opinions were contradictory). Quinoline derivatives are less zwitterionic by character than the respective pyridyl congeners. The β-diketone form itself may also be rarely present in the solution. X-ray data show that 2-(2(1H)-pyridinylidene)-1H-indene-1,3(2H)-dione, i.e., enaminone tautomer of 2-(pyridin-2-yl)-2H-indene-1,3-dione, is also the only form present in crystal. Ab initio calculations show that the enaminone is usually more stable than other tautomeric forms. Values of geometry based aromaticity index HOMA (harmonic oscillator model of aromaticity) confirm that the zwitterionic structure really contributes to the enaminone forms detected.
Silica gel catalyzed synthesis of quinophthalone pigments under solvent-free conditions using microwave irradiation
Loghmani-Khouzani, Hossein,Sadeghi, Majid M.,Safari
, p. 135 - 139 (2007/10/03)
Condensations of anhydrides and quinaldine derivatives are accelerated by microwave irradiation under solvent free conditions in the presence of silica gel as catalyst.
Synthesis and pharmacological evaluation of 2-(2 and 4- pyridinyl)indane-1,3-diones and structuraly related compounds exerting potential anti-inflammatory and antitumoral activities
Robert-Piessard,Leblois,Courant,Baut,Petit
, p. 160 - 168 (2007/10/03)
Our on going work in the series of enamido-diketones issued from 2- azaarylindane-1,3-diones led us to synthesize and experiment N and C2- substituted derivatives of 2-(2 and 4-pyridinyl)indane-1,3-diones as well as of structurally related compounds resulting from the replacement of pyridine by quinoline and benzimidazole. Pharmacological evaluation of their anti- inflammatory activity (by inhibition of carrageenan foot edema) and their anticoagulant activity (by prothombin assay) led to the conclusion of the possibility of achieving a selective antiinflammatory effect. It has been previously established that anticoagulants are liable to exert a protective effect in the development of cancer metastasis. Nevertheless none of the six experimented 2-(pyridin-2-yl)indane-1,3-diones extended survival time of mice treated by P388 lymphocytic leukemia.
ISOLEMENT PAR CHROMATOGRAPHIE LIQUIDE A HAUTE PERFORMANCE PREPARATIVE D'APPARIEMENT D'IONS ET IDENTIFICATION DES CONSTITUANTS MAJEURS DU JAUNE DE QUINOLEINE (C.I.47005)
Masiala-Tsobo, C.,Gelbcke, M.,Dumont, L.,Parmentier, F.,Grimee, R.
, p. 227 - 236 (2007/10/02)
A qualitative and quantitative study of the constituents of quinoline yellow (C.I.47005) in several samples is presented here.The isolation through preparative ion pairs HPLC of these constituents, followed by a spectroscopic examination (UV-visible, IR,1H-NMR) and by a study which compares them to synthesized derivatives, shows that quinoline yellow commercial samples contain chiefly disodic salts of 2-(2'-quinoyl)-1,3-indandione sulfonic acids sulfonated respectively on 5,6' and 5,8' positions.Some samples contain also important quantities of the last mentioned compound methylated on 6' position.