Enaminones as Bulding Blocks in Organic Synthesis: Synthesis of New Polyfunctional Pyridines, Condensed Pyridines and Ρεντα Substituted Benzene (original) (raw)
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Archiv der Pharmazie, 1991
The pyridine derivatives 4 and 10 are obtained by condensing paminocrotononieile (la) with malononib'ile. Compound 4 affords the pyridylpyridadne NitrUe in der Heterocyden-Synthese: Neue Wege zu polyfunktiond substitulerten Pyrldinen, Pyrldopyridinen, Chinolinen und Pyrldazlnen 7 on coupling with aryldiazonium salts. The reaction of la with cyan* thioacemide affords which the ae,,,,[2,34iP~h 13 on treatbensylidenemalononite (14). A variety of new pyridines. cyclohexadiene. and pyridopyridine derivatives wen obtained from d o n of2-~l-propene-l,1,3-tricarbonieille (it,) and diethyl 3-amino-2cyanopent-2-enedioate. (lc) with Mlcht-systems. Reaction of l b with acrylonib'ile afforded an acyclic diadduct 25 which could be c y c l i to the aminoquinolhe 26. Die Wdine 4 und 10 wurden durch Kondensation von &Aminocrotonnitril pyridazin 7 durch Kupplung mit Diazoniumsalzen-Reaktion von la mit ~O t h i o a c e t a m i d lief& u. das seinerseits Illit Phv'bom zu dm menot23-blpyridm 13 re@* Das Pyrido[23-blpyridin 15 enwht u mit B e m y l i d e n-m a l o d t. zahlniche new Pyridine, Cyclohexadiene und Pyridopyridine entstanden durch Reaktion von 2-Amino-l33-tricyanopropen (lb) bzw. dem Diethylester der ~A m i n o-~x y m e t h y l-a c r y I~ (lc) mit cgfhngesilaigten Carbonylverbiiungen. Die U m s e m g von l b mit Acrylnitril fIUute zu einem Diaddulct 25. das m Aminochinolin 26 zylclisien wurde.
New One Pot-synthesis of Functionally Substituted Pyridines from Enaminoketones
Journal of Heterocyclic Chemistry, 2014
Several new pyridine derivatives were prepared via reaction of enaminoketones 1a-d with active hydrogen reagents. Reaction of the enaminoketones 1a-c with 4-acetyl-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one 2a yielded the pyridines 3a-c. Condensation of the enaminonitrile 1d with compounds 2b-d and compound 8 gave the pyridine derivatives 6a-c and 10, respectively. Also, (3-(dimethylamino)acryloyl)-2H-chromen-2-one 1a reacted with active methylenes in diethyl 3-oxopentanedioate 12 and 4-methyl-6-oxo-2-thioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile 15 to afford the pyridine derivatives 14 and 16, respectively.
Studies on pyrrolidinones. Synthesis of new α-pyridones derivatives
Journal of Heterocyclic Chemistry, 2003
Dimethyl 7-methoxycarbonylmethyl-5-oxo-1,2,3,5-tetrahydro-indolizine-3,8-dicarboxylate was synthesized starting from methyl pyroglutamate. A study was made of the reactions of this highly functionalized pyridone with ethyl iodide, selenium oxide, isoamyl nitrite and formaldehyde. Literature reports that reaction of 4-(1-carbomethoxypropyl)-5-carbomethoxy-1,6-cyclopentano-2-pyridone with formaldehyde lead to a 95% yield of a monolactone precursor of camptothecin. Our experiments resulted in 15 % of this monolactone and 40% of a new dilactone (27). J. Heterocyclic Chem., 40, 45 (2003).
Egyptian Journal of Chemistry, 2018
A CETOACETANILIDE derivative 1 was reacted with aromatic aldehydes 2 to yield the arylidine derivatives 3 and 6a, b. The Hantzsch amides 7a,b were prepared by the one-pot cyclization reaction of a mixture of 2 moles of 1, aqueous ammonia and aromatic aldehydes. Treatment of 1 with ethanol containing equivalent amount of piperidine or morpholine furnished the isolable products 8a and 8b. Compound 1 underwent interamolecular heterocyclization on boiling conc. sulfuric acid, afforded 9. Also, the reaction of compound 1 with hydroxylamine hydrochloride in ethanol and sodium acetate afforded the oxime derivative 10. Furthermore, reactions of compound 1 with o-aminothiophenol furnished 11. Reactions of 1 with arylidine derivatives give compounds 13 and 16a-d. Treatment of compound 16d with elemental sulfur afforded the thieno[3,4-c]pyridine derivative 18. Treatment of 16a with hydrazine hydrate in boiling ethanol afforded the pyrazolo[3,4-b]pyridine derivatives 19. Also, compound 16a was reacted with ethylchloroacetate giving 20. Compound 20 was cyclized into the corresponding thieno[2,3-b]-pyridine derivative 21 upon boiling with ethanol containing a few drops of sodium ethoxide solution. Furthermore, compound 1 readily reacted with cyanothioacetamide to yield compound 22. Fusion of compound 1 with malononitrile over melting point without solvent in presence of ammonium acetate or refluxing in ethanolic piperidine afforded the pyridone 23a. Also, the pyridone derivative 23b was obtained by reacting compound 1 with cyanoacetamide. The reaction of acetoacetanilide 1 with ω-bromoacetophenones afforded 28a,b. Treatment of 1 with benzoyl and ethoxy carbonyl isothiocyanates afforded the pyrimidine derivatives 30a,b. The reaction of 1 with aminopyrazole gave the pyrazolopyrimidine 33. Coupling of 1 with diazonium salt of compounds 34a,b yielding 37a,b.
Journal of the Serbian Chemical Society, 2010
2-Chloro-4H-pyrido[1,2-a]pyrimidin-4-one (1) was utilized as a synthone precursor to prepare novel heterotricyclic systems. 2-Azido and 2-hydrazino derivatives (2 and 3) were obtained by nucleophilic replacement evolving compound 1. The hydrazine derivative 3 was transformed into the azido derivative 2 by nitrosation. Treatment of compound 3 with [bis(methylthio)methylene]malononitrile afforded 2-pyrazolylpyridopyrimidine 4. When compound 1 was reacted with 5-amino-3-(methylthio)-1H-pyrazole-4-carbonitrile, the same compound 4 was obtained with no evidence for the production of (pyrazolylamino)pyridopyrimidine 5 or pyrazolodipyridopyrimidine 6. Poly-functionalized dipyridopyrimidine 8 was obtained by reaction of compound 1 with 2-[(methylthio)-(phenylamino)methylene]propanedinitrile. Cyanoguanidine was reacted with compound 1 to afford N-pyridopyrimidinylguanidine 9, which was subjected to cyclization reaction, in presence of piperidinium acetate, to give pyridopyrimidopyrimidine 10.
Monatshefte Fuer Chemie Chemical Monthly, 2014
2-Chloro-6-ethoxy-4-phenylpyridine-3,5dicarbonitrile was taken as versatile building block that allows the synthesis of 1H-pyrrolo[2,3-b]pyridine, thieno[2,3-b]pyridine and pyrido[2 0 ,3 0 :5,4]pyrrolo[2,3-b]pyrimidine systems. Some of the synthesized compounds were screened as antibacterial agents.