Synthesis of some 1- and 2-carboxyalkyl substituted benzimidazoles and their derivatives

Mono- and disubstituted benzimidazoles were synthesized during alkaline hydrolysis or reactions with ethyl chloroacetate of 1-phenyl substituted 4-(1H-benzimidazol-2-yl)-2-pyrrolidinones. The properties of the synthesized ethyl-[2-(1-(substituted phenyl)-5-oxopyrrolidinyl-3-yl)-1H-benzimidazolyl]ethanoates have been investigated and their benzimidazolium chlorides, 1-carboxymethylbenzimidazoles, condensation products of 2-{2-[1-(3-methylphenyl)-5-oxo-3-pyrrolidinyl]-1H-benzimidazol-1-yl}acetohydrazide with various aromatic aldehydes and aliphatic ketones have been obtained.     

Synthesis of some heterocyclic derivatives of adamantane

The reaction of bromomethyt(1-adarnantyl)ketone with urea, thiourea, ammonium formate, and thiosemicarbazide gave a series of new imidazolin-2-ones, imidazolin-2-thiones and 2-aminothiazoles in the adamantane series.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 249–252, February, 1994. Original article submitted October 5, 1993.     

New synthesis of alkyl derivatives of adamantane

Conclusions A study was made of the isomeriztion of cyclic butadiene trimers on organoaluminum compounds and it was shown that dimethyladamantane can be synthesized from these products.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1631–1632, July, 1974.     

Preparation of 1-aminomethylenemercapto derivatives of 2, 4, 6, 8-tetrathiaadamantane and adamantane

1-Aminomethylenemercapto derivatives of 3, 5, 7, 9, 9-pentamethyl-2, 4, 6, 8-tetrathiaadamantane and adamantane were obtained by aminomethylation of 3, 5, 7, 9, 9-pentamethyl-2, 4, 6, 8-tetrathiaadamantane-l-thiol and adamantane-1-thiol.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 658–660, May, 1976.     

Design and synthesis of bioactive 1,2-annulated adamantane derivatives

Adamantanopyrrolidines 8, 9 and 10, adamantanopyrrolidines 16 and 18, adamantanoxazolone 20, adamantanopyrazolone 23, adamantanopyrazolothione 24 and adamantanocyclopentanamine 32 were synthesized and tested for anti-influenza A virus and trypanocidal activity. The stereoelectronic requirements for optimal antiviral and trypanocidal potency were investigated. Pyrrolidine 16 proved to be the most active of the compounds tested against influenza A virus, being 4-fold more active than amantadine, equipotent to rimantadine and 19-fold more potent than ribavirin. Oxazolone 20 showed significant trypanocidal activity against bloodstream forms of the African trypanosome, Trypanosoma brucei, being approximately 3 times more potent than rimantadine and almost 50-fold more active than amantadine.     

Synthesis of azolyl-substituted adamantane derivatives and their coordination compounds

Russian Chemical Bulletin - Reactions of adamantylazoles with nucleophiles (water, carbon monoxide, acetonitrile) in sulfuric acid were studied. New bifunctional adamantane derivatives containing...     

The synthesis of some phenothiazinyl ketones and their derivatives

The synthesis of a number of 2-chloro-8-acylphenothiazines via the Friedel-Crafts reaction has been reported. A series of dialkylaminoalkyl ketones have been derived from 2-chloroacetyl- and 2-chloro-8-chloroacetylphenothiazines. A number of dialkylaminoalkyl esters of 2-phenothiazinecarboxylic acid have also been synthesized.     

Preparation and properties of some α-aza-amino-acid derivatives,their possible use in peptide synthesis

Some derivatives of azaglycine and azaphenylalanine are described. Esters of acetyl- and benzoyl-aza-amino-acids rapidly cyclise to stable oxadiazolones and it is concluded that similar derivatives would be unsuitable for aza-peptide synthesis. t-Butyloxycarbonyl-azaglycine azide was too unreactive for use in peptide synthesis. Benzoyl-azaglycylphenylalanine ethyl ester and acetyl-azaphenylalanylphenylalanine ethyl ester were prepared by coupling benzoyl hydrazide and N-acetyl-N'-benzylhydrazide respectively with 2,4-dinitrophenyloxycarbonyl-phenylalanine ethyl ester.     

Synthesis of 1-polyfluoroalkoxy derivatives of adamantane

Features of synthesis of 1-polyfluoroalkoxy derivatives of adamantane via reactions of polyfluoroalkyl chlorosulfites with 1-adamantanol and of alcoholates of polyfluororinated alcohols with 1-bromoadamanatane were revealed.     

Synthesis of adamantane derivatives—XXX: Synthesis of some adamantane spiro heterocycles by utilizing ionic- and cycloadditions

Synthesis and some reactions of adamantane spiro heterocycles such as aziridine, oxaziridine, azetidine and 1,2-diazetidine derivatives have been described.The 1,3-dipolar cycloadditions of methyleneadmantane (2) and adamantylidenecyanoacrylate (14) have also been reported as a facile route to some 5-membered adamantane spiro heterocycles.     

Preparation and structures of some new 1H-pyrazole derivatives

Some new 3,5-diaryl-1H-pyrazoles were prepared from aryl methyl ketones via Claisen condensation with aromatic esters and followed by cyclization with hydrazine monohydrate. Their structures were confirmed by IR, ¹H NMR spectroscopy, mass spectrometry and elemental analysis. The X-ray structure for 3(5)-(4-tert-butylphenyl)-5(3)-(4-methoxyphenyl)-1H-pyrazole (2b) was presented. The results show that compound 2b exists as tautomers I and II, and its molecules are connected by the N–H···N intermolecular hydrogen bonds to form cyclic dimers consisting of the tautomers I and II.     

One-pot synthesis of some 2H-Pyran-2-one derivatives

A one-pot synthesis of various 2H-pyran-2-one derivatives 5–19 starting from methyl ketones 1 , N,N-dimethylformamide dimethyl acetal and N-acylglycines 3 in acetic anhydride is described.     

Electroreductive synthesis of 1-(bromobenzyl)-isoquinoline derivatives and its application to cularine synthesis

Electrochemical reduction of immonium salts in the presence of bromobenzylbromide derivatives gave 1-(bromobenzyl)-isoquinoline derivatives in moderate yields. This reaction is useful in the synthesis of several natural alkaloids as exemplified in the synthesis of Cularine.     

Preparation andH-NMR spectra of some adamantane derivatives: 2-formyladamantane, 2-bromo-3-methyl-2-homoadamantene, 4,4-adamantylene-1,3-dioxanes and some geminal substitued adamantanes, including 2-adamantylenecyclobutanone

A new two-step synthesis for 2-formyladamantane (3) from adamantanone is described. The Prins reaction of alkylidene-adamantane affords 4,4-adamantylene-1,3-dioxanes (9) and -2-adamantyl-alkanals (10), but no 5,5-adamantylene-1,3-dioxanes. The brominolysis of 2,2-ethyleneadamantane results in 2-bromo-3-methyl-2-homoadamantene (13). No 2,2-carbonsubstituted adamantane derivatives were obtained by reaction of organometallic reagents on adamantyleneoxirane. Grignard reagent may easily open the oxirane moiety by action of magnesium iodide, present in the reaction medium. A one-step synthesis of 2-adamantylenecyclobutanone from adamantanone and difenylsulfonium cyclopropylide is described. Some representative 300 MHz¹H-NMR spectra are given and discussed.