Facile and convenient synthesis of pyrimidine, 4H -3,1-benzoxazin-4-one, pyrazolo(5,1-b)quinazoline, pyrido(1,2-a)quinazoline, and (original) (raw)
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Turkish Journal of Chemistry, 2011
Facile and convenient synthesis of pyrimidine, 4H -3,1-benzoxazin-4-one, pyrazolo[5,1-b]quinazoline, pyrido[1,2-a]quinazoline, and chromeno[3 ,4 :4,5]pyrido[1,2-a]quinazoline derivatives A convenient synthesis of a series of pyrimidine, 4 H -3,1-benzoxazin-4-one, pyrazolo[5,1-b]quinazoline, pyrido[1,2-a]quinazoline, and chromeno[3 ,4 :4,5]pyrido[1,2-a]quinazoline derivatives, via the reactions of versatile and readily accessible methyl 2-(2-cyanoacetamido)benzoate (1) with the appropriate reagents, is described here.
Turk J …, 2011
Facile and convenient synthesis of pyrimidine, 4H -3,1-benzoxazin-4-one, pyrazolo[5,1-b]quinazoline, pyrido[1,2-a]quinazoline, and chromeno[3 ,4 :4,5]pyrido[1,2-a]quinazoline derivatives A convenient synthesis of a series of pyrimidine, 4 H -3,1-benzoxazin-4-one, pyrazolo[5,1-b]quinazoline, pyrido[1,2-a]quinazoline, and chromeno[3 ,4 :4,5]pyrido[1,2-a]quinazoline derivatives, via the reactions of versatile and readily accessible methyl 2-(2-cyanoacetamido)benzoate (1) with the appropriate reagents, is described here.
Synthesis of Novel Quinazoline Derivatives via Pyrimidine ortho-Quinodimethane
Molecules, 2002
The [4+2] cycloaddition between 2,4-diphenylpyrimidine ortho-quinodimethane and dimethyl acetylenedicarboxylate leads to 2,4-diphenylquinazoline-6,7-dicarboxylate (6). 2,4-Diphenylfuro[3,4-g]quinazoline-6,8-dione (7) is also obtained by basic hydrolysis of compound 6, followed by the closure of the resulting diacid in acetic anhydride.
Arkivoc, 2008
Treatment of 2-cyano-N-(2-pyridyl)acetamide (1) with hydrazonoyl chlorides 2a-e afforded aminopyrazoles 4a-e which on treatment with sodium nitrite in acetic acid furnished the pyrazolo[3,4-d]-1,2,3-triazin-4-one derivatives 8a-e. Reaction of aminopyrazoles 4c-e with triethylorthoformate in glacial acetic acid afforded pyrazolo[3,4-d]pyrimidin-4-one derivatives 10a-c. Compound 1 reacted with DMF-DMA in refluxing xylene affording a mixture of 3-(N,Ndimethylamino)propenenitrile 11 and N,1-di(pyridin-2-yl)pyridine-3-carboxamide 15 derivatives. When compound 11 was treated with hydrazine, phenylhydrazine or with 5-amino-3-phenyl-1H-pyrazole 16 in refluxing ethanol, the novel aminopyrazoles 13a,b and pyrazolo[1,5a]pyrimidine 18 derivatives were obtained.
A Convenient Synthesis of Regioisomeric Pyrazolo-Pyrimidine and Pyrazolo-Oxazine Derivatives
2015
Les pyrazolo[3,4-d]pyrimidines et pyrazolo[4,3-d]pyrimidines ont été préparés via réarrangement de Curtius des 4-methoxycarbonyl-1,3-diphenyl-5-carboxypyrazole et 5-methoxycarbonyl-1,3-diphenyl-4-carboxypyrazole suivi d'une condensation d'une série d'α- aminoacides. L'addition d'anhydrides appropriés sur les amino-acides pyrazoliques permet l'obtention des pyrazolo[3,4-d]oxazines et pyrazolo[4,3-d]oxazines avec de bons rendements.
Heteroatom Chemistry, 2004
Condensation of 4-aminoantipyrine with ethyl acetoacetate, ethyl benzoylacetate, and ethyl cyanoacetate furnished the corresponding ethyl 3-(1,2dihydro-1,5-dimethyl-2-phenyl-3-oxo-3H-pyrazol-4yl)aminoacrylate and 2-cyano-N-[(1,2-dihydro-1,5dimethyl-2-phenyl-3-oxo-3H-pyrazol-4-yl)]acetamide derivatives. The aminoacrylates derivatives react with acetonitrile and sodium hydride to give 2-amino-6methyl-1-(1,2-dihydro-1,5-dimethyl-2-phenyl-3-oxo-3H-pyrazol-4-yl)-4-pyridone. Reaction of the cyanoacetamide derivative with dimethylformamidedimethylacetal (DMF-DMA) afforded 2-cyano-N-[1,2dihydro-1,5-dimethyl-2-phenyl-3-oxo-pyrazol-4-yl]-2-(N,N-dimethylamino)methylene acetamide in high yield. Treatment of the latter with 5-aminopyrazole derivatives afforded the corresponding pyrazolo[2,3a]pyrimidines. 2-cyano-N-[(1,2-dihydro-1,5-dimethyl-2-phenyl-3-oxo-3H-pyrazol-4-yl)]acetamide also reacts with heterocyclic diazonium salts to give the corresponding pyrazolo[5,1-c]-1,2,4-triazine derivatives.
Synthesis of Some Quinazolines and Imidazolo-[1,5-a]-3,1-benzoxazine-4-one Derivatives
Rafidain journal of science, 2008
Some substituted N-methylene-2-(3,1-benzoxazonyl-4-one) amide (3a-c) were prepared from reaction of acetic anhydride with N-acyl anthranilic acid (2a-c) was synthesized from anthranilic acid with acyl glycinyl chloride. Treatment of (3a-c) with POCl 3 gave imidazolo-[1,5-a]-3,1-benzoxazin-4-one (4a-c). Quinazoline derivatives (6a-c) were prepared by reaction of methyl anthranilate with imidoyl chloride, the resulting esters were then converted to the hydrazides (7a-c). The synthesized compounds were identificated by IR and UV spectra.
Synthesis and antimicrobial activity of pyrazolo [3, 4-b] quinolines containing pyrimidine moiety
Indian Journal of …, 2011
2-Amino-pyridine-3-carboxaldehyde and 3-cyclopropyl-3oxopropionic acid ethyl ester react each other to provide 2-cyclopropyl-[1,8]-naphthyridin-3-carboxylic acid ethylester (1) which reacts with 99 % hydrazine hydrate to yield 2-cyclopropyl-[1,8]-naphthyridine-3carboxylic acid hydrazide (2). This acid hydrazide (2), reacts with different acetophenones to yield respective Schiff bases (3a-h). Compounds 3a-h react with Vilsmeier-Haack reagent (DMF/POCl3) to furnish 1-(2cyclopropyl-[1,8]-naphthyridine-3-carbonyl)-3-phenyl-1H-pyrazole-4carbaldehydes (4a-h). 2-Cyclopropyl-[1,8]-naphthyridine-3-carboxylic acid hydrazide (2) on reaction with substituted acetylacetones and substituted ethyl acetoacetates gives substituted 2-cyclopropyl-[1,8]naphthyridin-3-yl)-(3,5-dimethyl-pyrazol-1-yl)-methanones (5a-d) and 2-(2-cyclopropyl-[1,8]-naphthyridine-3-carbonyl)-5-methyl-2,4dihydropyrazol-3-ones (6a-c), respectively. On the other hand, hydrazide (2) reacts with different aromatic aldehydes yields 2-cyclopropyl-[1,8]naphthyridine-3-carboxylic acid benzylidene-hydrazides (7a-g). Compounds (7a-g) on reaction with mercapto-acetic acid offered 3-[(2-cyclopropyl-[1,8]-naphthyridin-3-yl-methyl)amino]phenyl-thiazolidin-4-ones (8a-g). Interaction of acid hydrazide (2) with different aromatic acid chlorides afford N'-acetyl/benzoyl-2-cyclopropyl-1,8-naphthyridine-3-carbohydrazides (9a-d), which on treatment with POCl3 yield 2-cyclopropyl-[1,8]-naphthyridin-3-yl)-(5-phenyl-[1,3,4]-oxadiazol-2-yl)methanone (10a-d). -carboxylic acid ethyl ester.
HETEROCYCLES, 2007
Cyanoacetamides (7a-c) were prepared via reacting cyanoacetic acid (5) with amines in the presence of acetic anhydride. Compounds (7a-c) coupled with benzenediazonium chloride to yield the phenylhydrazones (8a-c). These reacted with chloroacetonitrile to yield aminopyrazolecarboxamides (11a-c). Reaction of (8a,b) with hydroxylamine hydrochloride in DMF in presence of anhydrous sodium acetate afforded the amino-1,2,3-triazolecarboxamides (36a,b). Also compounds (7a-c) reacted with dimethylformamide dimethylacetal (DMFDMA) to yield the enamines (9a-c) which react with hydrazine hydrate to afford the aminopyrazoles (16a-c). Compounds (16) and (36) reacted with DMFDMA to yield the title heterocyclic derivatives.