Indoline spirochromenes with condensed fragments in the indoline part of the molecules were synthesized. All of the compounds have photochromic properties. The introduction of a condensed fragment into the indoline part of the molecule leads to a bathochromic shift of both the long-wave and short-wave absorption bands of the photomerocyanine; the rate of the dark reaction does not change.
Continuing our investigation of the relationship between the structures of indolinospirochromenes and the parameters of their photochromic transformations [i] we accomplished the synthesis and studied the photochromic properties of spirochromenes of the I-VII type: la~d~ llc, d III a-d~ IVa-d "Va-d VIc CH~O cn=O I Z=CH2; II Z=co; a R=H, R'=NO2; b R=Br, R'=NO2; c R=OCH3, R~=NO2; d R=NO~. RI=OCH~ The synthesis was carried out via the traditional scheme starting from 2-aminofluorene [2, 3], 2-aminofluorenone [4], 2-aminodibenzothiophene [5, 6], 3-aminodibenzothiophene [6], and 6-aminotetralin [7, 8]. By diazotization of the indicated amino derivatives with subsequent reduction of the diazonium salts with stannous chloride we obtained the corresponding arylhydrazines, from which arylhydrazones were formed by reaction with methyl isopropyl ketone. Fischer cyclization gave trimethylindolenines, methylation of which with methyl iodide led to tetramethylindoleninium iodides with annelated fragments. Decomposition of the quaternary indoleninium salts with alkali gave methylene bases, condensation of which with substituted salicylaldehydesyielded indoline spirobenzopyrans (Table i).