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81 5-AminoFischer’s base was condensed with the diacid chlorides of glutaric, pimelic, and azelaic acids to give in 70–92% yields the bis-amides, which upon reaction with 5-nitrosalicylaldehyde gave 70–88% of the bis-spiropyrans (72, n = 3,5,7). The alternative route, reaction of the acid chlorides with 5'-amino-6nitroBIPS, is impractical because of the difficulty of obtaining this BIPS. The bisBIPS exhibit strong photochromism. 4. Substitution in Spiropyrans The spiropyrans can be brominated with N-bromosuccinimide (NBS) in chloroform to give various substitution patterns that are dependent upon the nature of the two halves of the molecule.
In a third approach, one can prepare a spiropyran and then introduce new substituents, or transform substituents already present. Scheme 2 14 Robert C. Bertelson The first method is perhaps the most common, and is exemplified by the condensation shown in Scheme 3 of a 2-alkyl heterocyclic quaternary salt or the corresponding methylene base with a 2-hydroxy unsaturated aldehyde grouping (which usually is part of an aromatic ring, as in salicylaldehyde). These intermediates have given a broad assortment of spiropyran classes.
These were used as intermediates for cyanine dyes; their conversion to spiropyrans was not recorded. , in the 5,6-position) were prepared from 6-amino-1,2,3,3-tetramethylindoline by reaction with acetoacetic ester to give an 86% yield of the 1,2,3,3,5-pentamethyl-2,3,7,8tetrahydro-1 H ,8H -pyrrolo[3,2-g]quinolin-7-one (32), converted to the corresponding 7-chloroquinoline (33) in 80% yield with phosphorus oxychloride. Both the chloroquinoline and its precursor quinolone gave the corresponding Fischer’s base upon oxidation with mercuric acetate.
Advanced chemical oxidation treatment of dye wastewater and remediation of chlorinated aromatic