Chemistry of enol ethers. LXXXIII. Synthesis and investigation of penta- and hexacarbocyanine dyes containing cyclic fragments in the polymethine chain
4,6-Dimethylene- and 4,6-trimethylene-1,1,3,7,9-4,8-nonadienes were obtained by the reaction of 2,4-dimethylene- and 2,4-trimethylene-1,1,5,7-tetraethoxy-2,6-heptadienes with vinyl ethyl ether. Treatment of the products with N-methylaniline in an acidic medium gave the corresponding nonamethine salts. Condensation of the latter with 2-methyl-3-ethylbenzothiazolium iodide led to thiapentacarbocyanine dyes having symmetrically arranged di- and trimethylene bridges between the meta atoms of the polymethine chain. The reaction of glutaconaldehyde acetal with the cyclic 1-alkoxy-1,3-dienes led to the synthesis of 2,4-dimethylene- and 2,4-trimethylene-1,1,5,9,9-pentaalkoxy-2,6-nonadienes, from the thiapentacarbocyanines with an unsymmetrical arrangement of the dimethylene and trimethylene bridges were obtained through the respective nonamethine salts. A thiahexacarbocyanine dye containing a trimethylene bridge was synthesized from the undercamethine salt obtained from the product from the reaction of 1,1,5,9,9-pentamethoxy-2,4-trimethylene-2,6-nonadiene with vinyl ethyl ether.
- Research Organization:
- M.V. Lomonosov Moscow Institute of Fine Chemical Technology (USSR)
- OSTI ID:
- 6008606
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:4; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ABSORPTION SPECTRA
ACETALS
ACTIVATION ENERGY
ALCOHOLS
ALDEHYDES
AZOLES
BORON COMPOUNDS
BORON FLUORIDES
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CYANINE DYES
DEHYDROCYCLIZATION
DIENES
DYES
ENERGY
ENOLS
ETHERS
FLUORIDES
FLUORINE COMPOUNDS
HALIDES
HALOGEN COMPOUNDS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROXY COMPOUNDS
MOLECULAR STRUCTURE
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
POLYENES
SPECTRA
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
THIAZOLES
YIELDS