Synthesis of 2-aryl-3H-naphtho[1,2-d]imidazoles containing an adamantane fragment

N ²-[1-(1-Adamantyl)alkyl]naphthalene-1,2-diamines reacted with benzoyl chlorides in chloroform in the presence of triethylamine to give N-{2-[1-(1-adamantyl)alkylamino]naphthalen-1-yl}benzamides which underwent intramolecular cyclization to 2-aryl-3H-naphtho[1,2-d]imidazoles on heating in toluene in the presence of p-toluenesulfonic acid. 3-[(1-Adamantyl)methyl]-2-(3-nitrophenyl)-3H-naphtho[1,2-d]imidazole was synthesized from N ²-[(1-adamantyl)methyl]naphthalene-1,2-diamine and 3-nitrobenzaldehyde.     

Synthesis of 8-Aryl-7H-acenaphtho[1,2-d]imidazoles Using Fe3O4 NPs@GO@C4H8SO3H as a Green and Recyclable Magnetic Nanocatalyst

Russian Journal of Organic Chemistry - A general procedure has been developed for the rapid synthesis of 8-aryl-7H-acenaphtho[1,2-d]imidazoles in high yields using Fe3O4 NPs@GO@C4H8SO3H as a green...     

Synthesis of naphtho[1,2-d]imidazoles containing an adamantyl fragment

Russian Journal of Organic Chemistry -     

Synthesis of pyrimidine derivatives via multicomponent reaction catalyzed by ferric chloride

An eco-friendly and practical approach was developed for the synthesis of pyrimidine derivatives via a one-pot, three-component coupling reaction of commercially available aldehydes, alkynes, and indazole3/triazole catalyzed by ferric chloride with good to excellent yields. The advantages of this method include environmentally friendly catalyst, easily available materials, and ease of product isolation.     

Transformations of substituted tetrahydro-8h-indeno[1,2-d]imidazoles in concentrated sulfuric acid

The five-membered ring of the indene system in 2,8-dioxo-3a-hydroxy-8a-R-1,2,3a,8a-tetrahydro-8H-indeno[1,2-d]imidazoles is hydrolytically cleaved in concentrated sulfuric acid solutions. Depending on the reaction conditions, compounds for which substituted 4-(o-carboxyphenyl)imidazol-2-one (II), 1,8-dioxo-1,2-dihydro-8H-imidazo[4,3-a]isoindole (III), and spiro[imidazolidine-4,3′-phthalide] structures were assumed were isolated.     

一锅法合成新型7-苯基-10-芳基-5H-茚并[1,2-b]喹啉-9,11-二酮类化合物

以1,3-茚二酮,5-苯基-1,3-环己二酮和芳醛为原料,脯氨酸为催化剂,经"一锅法"合成了5个新型的7-苯基-10-芳基-5H-茚并[1,2-b]喹啉-9,11-二酮化合物,收率73%~80%,其结构经1H NMR,ESI-MS和元素分析表征。     

Synthesis and some transformations of 2-(2-thienyl)-1H-acenaphtho[1,2-d]imidazole

Three-component reaction of acenaphthenequinone, 9,10-thiophene-2-carbaldehyde and ammonium acetate in glacial acetic acid afforded 2-(2-thienyl)-1H-acenaphtho[1,2-d]imidazole. Its N-methylated product undergoes electrophilic substitution reactions (nitration, bromination, sulfonation, formylation, acylation) in KOH-1-methyl-2-pyrrolidone mixture. Depending on the reaction conditions electrophilic attack occurred at both thiophene ring and acenaphthene fragment.     

Poly(4-vinylpyridinium) hydrogensulfate catalyzed synthesis of 12-aryl-12H-indeno[1,2-b]naphtho[3,2-e]pyran-5,11,13-triones

A simple and facile synthesis of 12-aryl-12H-indeno[1,2-b]naphtho[3,2-e]pyran-5,11,13-trione derivatives was accomplished via the one-pot condensation of 2-hydroxynaphthalene-1,4-dione, aldehydes, and 2H-indene-1,3-dione at 100 °C under solvent-free conditions in the presence of the solid acid catalyst, poly(4-vinylpyridinium) hydrogensulfate. This method has the advantages of high yields, clean reactions, simple methodology, and short reaction times. The catalyst could be recycled and reused four times without significant loss of activity. The structures of the novel compounds were confirmed by IR, ¹H NMR, and elemental analysis.     

Green and Facile Synthesis of New 3-(Phenylallylideneamino)indeno[1,2-d]imidazoles

A green and facile strategy has been proposed for the synthesis of previously unknown 3a,8a-dihydroxy-3-[(3-phenylprop-2-en-1-ylidene)amino]-2-sulfanylidene-2,3,3a,8a-tetrahydro-1H-indeno[1,2-{und}]imidazol-8-one and 3a,8a-dihydroxy-3-[(3-phenylprop-2-en-1-ylidene)amino]-1,3,3a,8a-tetrahydroindeno[1,2-d]-imidazole-2,8-dione in excellent yields by condensation of cinnamaldehyde thiosemicarbazone and semicarbazone, respectively, with ninhydrin in boiling dioxane. The reaction is clean, simple, and free of work-up and column chromatography.

     

Synthesis of 7-substituted 1H-indolo[3,2-d][1,2]benzoxazepines

The synthesis of the novel 7-substituted 1H-indolo[3,2-d][1,2]benzoxazepine ring system is described. Fischer indolization of 2-fluoroacetophenone phenylhydrazone provided the starting material 2-(2-fluorophenyl)-1H-indole. An acyl group was then introduced at the 3-position of the indole nucleus and the resulting ketone was converted to the ketoxime. Upon treatment with sodium hydride to form the oxanion of the ketoxime, an intramolecular cyclization took place via displacement of fluoride from the adjacent 2-fluorophenylsubstituent. This ring closure completed the construction of the 1H-indolo[3,2-d][1,2]benzoxazepine ring system.     

Thermolyzed products of naphth[1,2-d]imidazo[2,1-b]-thiazole-2,3-dione

Themolysis of naphth[1,2-d]imidazo[2,1-b]thiazole-2,3-dione ( 1 ) in dimethylformamide gave an intermediate 2-isocyanatonaphtho[1,2-d]thiazole ( 2 ), which underwent [4 + 4] cyclodimerization to yield dinaphtho-[1″,2″:4,5;1′″,2′″:4′,5′]dithiazolo[3,2-a:3′,2′-e]-1,3,5,7-tetrazocine-9,19-dione ( 3 ). The possible [4 + 2] cycloadduct, 3-(2-naphtho-[1,2-d]-thiazolyl)naphtho[1′,2′:4,5]thiazolo[3,2-a]-1,3,5-triazine-2,4-dione ( 4 ), an usual dimer type of heterocyclic isocyanates was not produced. Discrimination between the two isomers was established on the basis of spectral analyses.     

Synthesis and properties of some derivatives of 2-thionoindeno [1,2-d]-pyrimidine and indeno [1,2-d] [3,1] thiazine

Derivatives of 2-thiono-5-oxo-2,3,4,5-tetrahydroindeno[1,2-d] pyrimidine and 5-oxo-1,2,4,5-tetrahydroindeno [1,2-d] [3,1] thiazine are formed in the cyclocondensation of 2-arylideneindan-1,3-diones with thiourea and N-monomethylthiourea, while only derivatives of indeno [1,2-d]-pyrimidine are formed in the reaction with N,N-di-methylthiourea. S- and N(₃)-Alkylation occur in the alkylation of 2-thiono-4-pheny1-5-oxo-2,3,4,5-tetrahydroindeno[1,2-d]pyrimidine, while only the N-methyl derivative is formed in the alkylation of 2,5-dioxo-4-phenyl-1,2,4,5-tetrahydroindeno [1,2-d] [3,1]thiazine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1136–1141, August, 1988.     

Synthesis of 4-aryl-6-phenyl-2-thioxo-1,2-dihydropyridine-3-carbonitriles by three-component condensation of aromatic aldehydes with cyanothioacetamide and 4,4,4-trifluoro-1-phenylbutane-1,3-dione

4-Aryl-6-phenyl-2-thioxo-1,2-dihydropyridine-3-carbonitriles were synthesized by three-component condensation of aromatic aldehydes with cyanothioacetamide and 4,4,4-trifluoro-1-phenylbutane-1,3-dione. The reaction involved initial formation of Michael adducts which underwent acyl cleavage.     

Synthesis of 3-aryl-6H-isoxazolo[3,4-d]pyrazolo[3,4-b]pyridines and 3-aryl-6H-isoxazolo[5,4-d]pyrazolo[3,4-b]pyridines

The synthesis and characterization of a number of 3-aryl-6H-isoxazolo[3,4-d]pyrazolo[3,4-b]pyridines and 3-aryl-6H-isoxazolo[5,4-d]pyrazolo[3,4–6]pyridines from common precursors, 5-benzoyl-4-chloro-1H-pyrazolo-[3,4-b]pyridines, has been described. The structures were determined by unambiguous chemical synthesis and by isolation and ¹³C nmr analysis of some key, isolated, intermediates. The ability of these compounds to displace [3H]flunitrazepam from CNS binding sites was also observed.     

Polycyclic systems: Synthesis of isoindolo[2,1-b]-pyrrolo[1,2-d][2,4]benzodiazocine and isoindolo-[1,2-d]pyrrolo[1,2-a] [1,5]benzodiazocine

The synthesis of isoindolo[2,1-b]pyrrolo[1,2-d][2,4]benzodiazocine 7 and isoindolo[1,2-d]pyrrolo[1,2-a]-[1,5]benzodiazocine 13 are described starting from 2-(2-methoxycarbonyl)benzylphthalimide 1a and ethyl α-bromohomophthalate 9 respectively.     

Synthesis and reactions of 1-benzylide neaminoimidazo[1,2-a]imidazoles

The method of synthesizing condensed imidazo-heterocyclic systems has been extended to the production of N-benzylideneaminoimidazo[1,2-a]imidazoles (VI, VII), the successive hydrolysis and treatment with nitrous acid of which has enabled N-substituted imidazo[1,2-a]imidazoles to be obtained. A by-product of the synthesis is 1,2-dibenzylideneamino-4-phenyl-5-n-propylimidazole (VIII), the condensation of the reduction product of which with isatin leads to a tetracyclic system.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1190–1193, September, 1973.     

Synthesis of 6-amino-2-aryl-1,2-dihydro-3H-pyrido[2,3-d]pyrimidin-4-one derivatives

This paper reports the synthesis of new pyrido[2,3-d]pyrimidin-4-one derivatives as diuretic agents. Starting with 1,2-dihydro-5-nitro-2-oxo-3-pyridinecarboxylic acid 1 , ethyl 2-ethoxy-5-nitro-3-pyridincarboxylate 4 was obtained. Compound 4 reacts with ammonia, methylamine or S-methylpseudothiourea to give the respective 2-amino-5-nitro-3-pyridinecarboxamide derivatives 5 and 6 or 2-methylthio-6-nitro-3H-pyrido[2,3-d]pyrimidin-4-one 8. Treating carboxamide 5 with arylaldehydes and zinc dichloride, new 2-aryl-1,2-dihydro-6-nitro-3H-pyrido[2,3-d]pyrimidin-4-ones 9 were synthetised. These compounds reduced with iron(II) hydroxide gave 6-amino-2-aryl-1,2-dihydro-3H-pyrido[2,3-d]pyrimidin-4-ones 10 as expected.