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The Duff formylation of 5 bromo or 5 chloro 8 hydroxyquinoline leads to the corresponding 7 formyl derivatives, condensation of which with 2 methyleneindolines or 3Н indolium halides in the presence of a base afforded new photochromic 6´ halo substituted spiro[indoline 2,2´ 2H pyrano[3,2 h]quinolines]. Thermal and photo induced isomerization of compounds obtained have been investigated by 1 Н NMR and UV spectroscopy.

Coordination chemistry Z 0150 Luminescent Complexes with Ligands Containing C=N Bond -[100 refs.]. -(METELITSA, A. V.; BURLOV, A. S.; BEZUGLYI, S. O.; BORODKINA, I. G.; BREN, V. A.; GARNOVSKII, A. D.; MINKIN, V. I.; Russ. J. Coord. Chem. (Transl. of Koord. Khim.) 32 (2006) 12, 858-868; Inst. Phys. Org. Chem., Rostov State Univ., Rostov-on-Don 344104, Russia; Eng.) -Lindner 51-229

New indolinospirochromenes have been synthesized containing a condensed furan fragment, an analog of the methoxyl substituent in position 6' of the chromene part of the molecule. Solutions of the obtained compounds display photochromic properties. For one of the compounds, depending on the temperature of irradiation, the cis-cisoid or trans-transoid isomer is fixed spectrally. An X-ray structural investigation has been carried out on crystals of spiropyrans possessing various forms of photoactivity in the solid phase.

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Photolysis of hexane solutions of quinolin 2 yl β tropolones is accompanied by the photo induced proton transfer O-H...N → O...H-N followed by the disrotatory electrocyclic rear rangement giving rise to 3 (1H quinolin 2 ylidene)bicyclo[3.2.0]hept 6 ene 2,4 dione deriva tives. The molecular and crystal structure of one of the compounds isolated preparatively, viz., 1,6 di(tert butyl) 3 (4 chloro 8 methyl 1H quinolin 2 ylidene)bicyclo[3.2.0]hept 6 ene 2,4 dione, was established by X ray diffraction. The structures, tautomeric transformations, and the structural dynamics of the resulting compounds were studied by ab initio quantum chemical methods, absorption and fluorescence spectroscopy, and dynamic NMR spectroscopy.

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