Synthesis and substituent effects of some novel dyes derived from indeno[2,1-b]thiophene compounds

Fu, Tzu Liang; Wang, Ing Jing

doi:10.1016/j.dyepig.2006.07.030

Cited by 14 publications

(2 citation statements)

References 21 publications

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“…Historically, polysubstituted 2-thiophenamines has an electron-attracting groups such as carbethoxy, cyano, or carboxamide in the 3-position and alkyl, aryl or hetaryl groups in the 4-and 5-positions have been produced by the Gewald reaction 4 . Moreover, 2-aminothiophene has incontestible a broad spectrum of uses together with production of prescription drugs 5 and dyes 6 and starting materials for the synthesis of amalgamated heterocyclic systems [7][8][9] . Thiophene will extraordinarily behave reactive like benzene in terms of getting a pie electron cloud structure.…”

Section: Introductionmentioning

confidence: 99%

Heterocyclization of 2-thiophenamine: Design of novel thiophene with azole and azine moieties

Hamed

Assy

El-Said

et al. 2022

Bulletin of Faculty of Science, Zagazig University

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Thiophenamine of type 1 undergo several functionalization and heterocyclization, thus reaction of target 1 with diethyl succinate furnished benzothiophene derivative 4 through condensation followed by intramolecular cyclocondensation and subsequent evolution of 3 H2. Keeping diethyl malonate and amino derivative 1 provide hydroxypyridine derivative 7, may be via 3 °r amine 5 that added the active methylene to the ester group followed by hydrolysis and subsequent decarboxylation. Also, Target 1 undergo cyclocondensation with ethyl acetoacetate to produce acetyl pyridine of type 10. Alkylation of 1 with N-phenyl chloroacetamide provided alkylation derivative 11. Acylation of compound 1 with chloroacetyl chloride followed by cyclization leads to chloropyrrole derivative 14. Compound 14 reacted with NH4SCN to give non isolable pyrrole 15 followed by enolization and subsequent intramolecular cycloaddition providing fused pyrrole 16. Compound 1 reacted with succinic anhydride and ethyl cyanoacetate to provide acylated derivative 17 and aminocyanopyridine 19, respectively. Compound 19 undergo azidolysis and acetylation producing pyridine derivatives 20 and 21, respectively. Compound 19 added its amino group to heteroallene electrophilic carbon of benzoyl isothiocyanate followed by intramolecular heterocyclization producing pyridopyrimidine derivative 23.

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Section: Introductionmentioning

confidence: 99%

Heterocyclization of 2-thiophenamine: Design of novel thiophene with azole and azine moieties

Hamed

Assy

El-Said

et al. 2022

Bulletin of Faculty of Science, Zagazig University

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“…There are two common variations on this synthesis: (a) one-pot procedure in which ketones or aldehydes react with an activated nitrile and elemental sulfur; and (b) two-step procedure in which alkene produced by the A Knoevenagel condensation is isolated prior to cyclization with sulfur and base, and the latter one is generally preferred and provides better yields (3) . Moreover, 2-aminothiophene has demonstrated a broad spectrum of uses including production of pharmaceuticals (4) and dyes (5) and starting materials for the synthesis of fused heterocyclic systems (6)(7)(8) . Also, indole being a potent basic pharmacodynamic nucleus, has been reported to possess a wide variety of biological properties viz, anti-inflammatory (9,10) , anticancer (11,12) and antimicrobial activities (13) .…”

mentioning

confidence: 99%

Some New 2-Amino-4-(N-substituted-1H- indol - 3-yl) thiophene-3-carbonitriles and their Antimicrobial Properties

2012

Egypt. J. Chem.

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NOVEL series of 2-amino-4-(N-substituted-1H-indol-3-yl) thiophene-3-carbonitriles (3a-f) were prepared via reaction of 2-(1-(N-substituted-1H-indol-3-yl) ethylidene) malononitriles (2a-f) with sulfur (Gewald reaction). Reaction of 3a-f with formic acid, formamide or malononitrile led to the formation of fused thieno [2,3d] pyrimidin-4(3H)-ones (6a-f) thieno[2,3-d] pyrimidin-4-amines (7a-f) and thieno[2,3-d] pyridine-3-carbonitriles (8a-f), respectively. On the other hand, a series of 2-(2-(4-nitrophenyl)-4-oxothiazolidin-3-yl)-4-(N-substituted-1H-indol-3-yl) thiophene-3-carbonitriles (10af) and N-3-[3-cyano-4-(N-substituted-1H-indol-3-yl)-(2-thienyl)-4oxo-2-imino thiazolidinylidenes (12a-f), were prepared via reaction of Schiff bases 9a-f with thioglycollic acid or reaction of chloroacetamids 11a-f with potassium thiocyanate, respectively. Moreover, reaction of 3a-f with ethylenediamine yielded 3-(4,5dihydro-1H-imidazol-2-yl)-4-(N-substituted-1H-indol-3yl) thiophen-2-amines (13a-f). The antimicrobial activity of the newly synthesized compounds revealed that, 2-(2-(naphthalene-1-yl)diazenyl)-4-(Nsubstituted-1H-indol-3-yl)thiophene-3-carbonitriles (4a-f) showed potent inhibition of 25-33 and 18-26mm at a dose of 20 and 10 μg per disc, respectively towards Aspergillus fumigatus compared to reference drug cycloheximide.

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Synthesis, Spectral Characterization and Pharmacological Evaluation of Ni(II) Complexes of 6-Nitro-benzothiazole Incorporated Azo Dyes

Ravi

Keshavayya

Mallikarjuna

2020

J Inorg Organomet Polym

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Synthesis and substituent effects of some novel dyes derived from indeno[2,1-b]thiophene compounds

Cited by 14 publications

References 21 publications

Heterocyclization of 2-thiophenamine: Design of novel thiophene with azole and azine moieties

Heterocyclization of 2-thiophenamine: Design of novel thiophene with azole and azine moieties

Some New 2-Amino-4-(N-substituted-1H- indol - 3-yl) thiophene-3-carbonitriles and their Antimicrobial Properties

Synthesis, Spectral Characterization and Pharmacological Evaluation of Ni(II) Complexes of 6-Nitro-benzothiazole Incorporated Azo Dyes

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