Abstract Several new thiazoles ( 3–7 ), thiazolylpyrazole carbonitrile ( 10 , 11 ), and Thiazolidine sulfonamido conjugate derivatives ( 19–26 ) were prepared starting with p-Piperidinesulfonylacetophenones ( 1 , 2 ). The structure of these compounds was elucidated on the bases of elemental analysis, IR, PMR, and mass spectra. The antimicrobial activities of some selected compounds are also reported. Keywords: p-Piperidinesulfonylacetophenonesthiazolethiazolidine-containing piperidine sulfonamidethiazolylpyrazol
2-Cyanomethyl-4-thiazolinone ( 1 ) was condensed with terephthalaldehyde ( 2 ) (2:1 molar ratio) and produced 1,4-bis(2-cyanomethyl-4,5-dihydro-5-methylidene-4-thiazolinone-5-yl) benzene ( 3 ). Treatment of compound ( 3 ) with benzylidenemalononitrile ( 4 ) (1:2 molar ratio) furnished the novel bisthiazolopyridines ( 6a-e ). Condensation of compound ( 1 ) with aromatic aldehyde yielded the benzylidene derivatives ( 7a-f ), which on treatment with compound ( 8 ) (2:1 molar ratio) afforded the novel bisthiazolopyridines ( 10a-f ). Structures of the synthesized compounds have been established by elemental analyses and spectral data.
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Condensation of thiazolinone 1 with benzaldehydes 2a, b in ethanolic piperidine afforded the methylidene derivatives 3a, b. Cyclocondensation of compound 3b with malononitrile furnished the novel thiazolo[3,2-a]-pyridine 5. Also, compound 3b was condensed with dimethylformamide-dimethylacetal (DMF-DMA) and triethylortho-formate to yield N,N-dimethylamino 6 and ethoxymethylene 7 derivatives respectively. The novel thiazolo[3,2-a]pyridines 10a, b were obtained by cyclocondensation of compounds 3a, b with benzylidene-malononitriles 8a, b. Similarly, cyclocondensation of compound 3b with benzylidenemalononitrile 11 afforded the thiazolopyridines 12a–c. Ternary condensation of compound (12), 4-morpholinobenzaldehyde 2b and malononitrile (1:1:1 molar ratio) produced the thiazolopyridines 14a–c. When compound 10b was subjected to react with malononitrile in dioxane/piperidine under reflux the novel condensed heterocyclic system 18 was obtained. Treatment of ortho-aminocarbonitrile 10b with formic acid, aromatic aldehyde and triethylorthoformate furnished the thiazolo[2′,3′:1,6] pyrido[2,3-d] pyrimidine 20, azomethine 21a, b and ethoxymethylene 22 derivatives respectively. The structure of the synthesized compounds was established by analytical and spectral data.
The synthesis of 6,8-diiodocoumarin derivatives (2-6) by condensation of 3,5-diiodosalicylaldehyde (1) with active methylene compounds is described. Reaction of 6 with malononitrile afforded two products pyridine and ethylidine malononitrile derivatives (7, 8), while treatment of 6 with p-methoxybenzylidenemalononitrile in absolute ethanol/piperdine provided pyrane and bis coumarin derivatives (9,10). Reaction of 6 with DMF/POCl3 afforded three products coumarin derivatives (11,12,13), while bromination of 6 with Br2/AcOH gave 3-bromo-6,8-diiodocoumarin (14). Treatment 6 with aromatic aldehydes gave the corresponding 3-(3-arylacryloyl)-6,8-diiodocoumarin derivatives (16a,b) while reaction of 6 with aniline or phenylhydrazine gave coumarin derivatives 17 and 18. Reaction of 18 with DMF/POCl3 gave pyrazole-4-aldehyde derivative (19). Condensation of 19 with active methylene compounds afforded pyrazole and pyrimidine derivatives (20a-c) and 21). Reaction of 8 with sulphur via the Gewald reaction afforded thiophene derivative (22), while the reaction of 8 with p-methoxybenzylidenemalononitrile gave biphenyl derivative (23). Treatment of 8 with chloroacetyl chloride afforded the furan derivative (24). The structures of the newly synthesized compounds were confirmed by IR, 1H NMR and 13C NMR and mass spectral data. The newly synthesized compounds were also screened for their antimicrobial activity.
Several novel naphtho[2,1-b]pyrano[2,3-d]pyrimidines, pyrano[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines and their coumarin-3-yl derivatives were synthesized. Some of these derivatives exhibited pronounced antimicrobial activities.