Synthesis of pyrrolo(2,3-g)benzothiazoles and their polymethine dyes

Journal Article · Tue Sep 20 04:00:00 EDT 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5971565

Dzyubenko, V G; Abramenko, P I

N-(2-methyl-6-benzothiazolyl)hydrazine was obtained from 2-methyl-6-aminobenzothiazole. Its condensation with methyl ethyl ketone was used for the synthesis of 2,7,8-trimethylpyrrolo(2,3-g)benzothiazole. The latter was converted into 2,6,7,8-tetramethylpyrrolo(2,3-g)benzothiazole by alkylation in the presence of a phase-transfer catalyst. 2-(/beta/-anilinovinyl) derivatives and polymethine dyes with symmetrical and unsymmetrical structures were obtained from the quaternary salts of the pyrrolobenzothiazoles. The dyes had a deeper color than the corresponding derivatives of furo- and thieno(2,3-g)benzothiazoles. There is also a bathochromic shift of the absorption maximum with substitution of a hydrogen atom in the pyrrole ring by a methyl group.

• Research Organization: All-Union State Scientific-Research and Design Institute of the Photographic Chemical Industry, Moscow (USSR)
• OSTI ID: 5971565
• 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

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ABSORPTION SPECTRA
ACTIVATION ENERGY
ALKYLATING AGENTS
ALKYLATION
AMINES
AMMONIUM CHLORIDES
AMMONIUM COMPOUNDS
AMMONIUM HALIDES
AZOLES
BENZOTHIAZOLES
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
COLOR
DEHYDROCYCLIZATION
DYES
ENERGY
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
HETEROGENEOUS CATALYSIS
HYDROGEN TRANSFER
IODINATED ALIPHATIC HYDROCARBONS
KETONES
MASS SPECTRA
METHYL IODIDE
MOLECULAR STRUCTURE
NMR SPECTRA
OPTICAL PROPERTIES
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
ORGANOLEPTIC PROPERTIES
PHYSICAL PROPERTIES
PYRROLES
QUATERNARY COMPOUNDS
SPECTRA
SPECTRAL SHIFT
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS
THIAZOLES