Synthesis of ethyl ({[adamantan-1(2)-ylalkyl]-carbamothioyl}amino)acetates

Reactions of adamantan-1(2)-amines and adamantan-1(2)-ylalkanamines with ethyl isothiocyanatoacetate afforded ethyl ({[adamantan-1(2)-ylalkyl]carbamothioyl}amino)acetates in 85–95% yields. The hydrolysis of ethyl {[(adamantan-2-yl)carbamothioyl]amino}acetate in alkaline medium resulted in the formation of {[(adamantan-2-yl)carbamothioyl]amino}acetic acid in a virtually quantitative yield.     

微波辐射下2-[4-二-(4-氟苯)甲基]哌嗪乙酰腙化合物的合成

微波辐射条件下, 以丙酮作溶剂, 1-[二-(4-氟苯)甲基]哌嗪与氯乙酸乙酯反应得到2-[二-(4-氟苯)甲基]哌嗪乙酸乙酯(1), 1与水合肼在微波辐射条件下反应得到2-[二-(4-氟苯)甲基]哌嗪乙酰肼(2), 进一步在微波辐射条件下由2-[二- (4-氟苯)甲基]哌嗪乙酰肼(2)与取代芳香醛反应制得目标化合物3a～3f. 合成的6个目标化合物通过熔点测定和质谱、红外光谱、核磁共振氢谱分析、元素分析对其结构进行确证.     

Synthesis of Chiral Ligands on the Basis of 1-(Adamantan-1-yl)ethane-1,2-diamine

Russian Journal of Organic Chemistry - The reduction of 1-(adamantan-1-yl)-2-azidoethan-1-one oxime with LiAlH4 gave racemic 1-(adamantan-1-yl)ethane-1,2-diamine, which was resolved with l-tartaric...     

Synthesis and Properties of Ethyl [(Adamantan-1-yl)alkylene(phenylene)amino]oxoacetates and N1,N2-Bis[(adamantan-1-yl)alkylene(phenylene)]oxamides

Russian Journal of Organic Chemistry - Ethyl [(adamantan-1-yl)alkylene(phenylene)amino]oxoacetates and N1,N2-bis[(adamantan-1-yl)-alkylene(phenylene)oxamides were prepared in yields of 72–87...     

Synthesis,Structure, and Anti-influenza Activity of 2-(Adamantan-1-yl)-5-aryl-1,3,4-oxadiazoles and 2-(Adamantan-1-yl)-5-aryltetrazoles

Two series of new adamantyl derivatives of polynitrogen heterocycles, 2-(adamantan-1-yl)-5-aryl- 1,3,4-oxadiazoles and 2-(adamantan-1-yl)-5-aryl-2H-tetrazoles, have been synthesized, and their structure has been determined by NMR spectroscopy, mass spectrometry, and X-ray analysis. Biological studies in vitro have revealed high inhibitory activity of some of the synthesized 2-(adamantan-1-yl)-5-aryl-2H-tetrazoles against H1N1 influenza A viruses in combination with a relatively low selectivity.     

Halocyclization of 2-(2-{4-[allylamino(thioxo)methyl]piperazin-1-yl}ethyl)-1<Emphasis Type="Italic">H</Emphasis>-benzo[<Emphasis Type="Italic">de</Emphasis>]isoquinoline-1,3(2<Emphasis Type="Italic">H</Emphasis>)-dione

Cyclization of 2-(2-{4-[allylamino(thioxo)methyl]piperazin-1-yl}ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione by the action of iodine, bromine, or sulfuryl chloride gave 2-(2-{4-[4,5-dihydro-5-(halomethyl)-thiazol-2-yl]piperazin-1-yl}ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione hydrohalides which were converted into 2-{2-[4-(5-methylthiazol-2-yl)piperazin-1-yl]ethyl}-1H-benzo[de]isoquinoline-1,3(2H)-dione.     

Kine-substitution in the N-[ω-(5-bromouracil-1-yl)alkyl]alkylamine series

In the reaction of N-[2-(5-bromouracil-1-yl)ethyl]alkylamines with alkylamines at 40 °C kine-substitution takes place with the formation of N-[2-(6-alkylamino-uracil-1-yl)ethyl]alkylamines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1260–1261, September, 1984.     

Dipolar additions with 1-(4,6-dimethylpyrimidin-2-yl)- and 1-(4,6-dimethoxy-s-triazin-2-yl)-3-oxidopyridinium betaines

Cycloaddition to 1-(4,6-dimethylpyrimidin-2-yl)- and 1-(4,6-dimethoxy-s-triazin-2-yl)-3-oxidopyridinium betaines across the 2,6-positions of the pyridine rings with indene, acenaphthylene and ethyl cinnamate gave substituted 8-aza[3.2.1]bicycIooct-3-en-2-ones, whereas the [6π + 4π] cycloaddition reaction with 6,6-dimethylfulvene gave a tricyclo[6.3.1.0^2.6]dodeca-2,(6),4,9-trien-11-one. Structural and configurational assignments of the cycloadducts were deduced from ¹H nmr and ir spectral data.     

SYNTHESIS AND CRYSTAL STRUCTURE OF THE COBALT(II) COMPLEX WITH 1-{1-[2-(o- TOLYLOXY)ETHYL]-1H-BENZIMIDAZOLE-2-YL}ETHAN-1-OL

Journal of Structural Chemistry - A Co(II) complex with 1-{1-[2-(o-tolyloxy)ethyl]-1H-benzimidazol-2-yl}ethan-1-ol is prepared. It is established by elemental analysis and IR spectroscopy that the...     

达比加群酯中间体3-【【【2-{[(4-氰基苯基)氨基]甲基}-1-甲基-1H-苯并咪唑-5-基】羰基】(吡啶-2-基)氨基】丙酸乙酯的合成

以对氨基苯腈为起始原料,经胺化反应制得N-(4-氰基苯基)甘氨酸(4);4与N-[3-氨基-4-(甲基氨基)苯甲酰基]-N-2-吡啶-β-丙氨酸乙酯(5)经酰胺化后经闭环反应,合成了达比加群酯的关键中间体——3-【【【2-{[(4-氰基苯基)氨基]甲基}-1-甲基-1H-苯并咪唑-5-基】羰基】(吡啶-2-基)氨基】丙酸乙酯,总收率79.6%,其结构经~1H NMR和ESI-MS确证。     

Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XIV. N-[(Adamantan-1-yl)(phenyl)methyl]-N′-substituted Ureas and Symmetrical Bis-ureas

Russian Journal of Organic Chemistry - A procedure has been developed for the synthesis of rac-1-[isocyanato(phenyl)methyl]adamantane from rac-2-(adamantan-1-yl)-2-phenylacetic acid in 95% yield....     

Stereospezifität der neuroleptischen Wirkung und Chiralität von (+)-3-{2-[4-(8-Fluor-2-methyl-10,11-dihydrodibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-äthyl}-2-oxazolidinon (16). 4. Mitteilung über tricyclische Antidepressiva und Neuroleptica

Stereospecifity of the neuroleptic activity and chirality of (+)-3-{2-[4-(8-fluoro-2-methyl-10, 11-dihydrodibenzo[b,f]thiepin-10-yl)-1-piperazinyl]ethyl}-2-oxazolidinone (16). The synthesis and stereospecific neuroleptic action in animals of the (+)-enantiomer of 3-{2-[4-(8-fluoro-2-methyl-10,11-dihydrodibenzo [b,f]thiepin-10-yl)-1-piperazinyl]ethyl}-2-oxazolidinone ( 16 ) are briefly described. The (10S)-configuration of this compound was determined by X-ray diffraction.     

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 1-[2-(1H-Indol-3-yl)ethyl]-4-acetyl-3-hydroxy-5-phenyl-1H-pyrrol-2(5H)-ones

Russian Journal of General Chemistry - 1-[2-(1H-indol-3-yl)ethyl]-4-acetyl-3-hydroxy-5-phenyl-1H-pyrrole-2(5H)-ones were synthesized by the short heating of a mixture of tryptamine, aromatic...     

Reaction of 2-(5-aminopyrazol-1-yl)quinoxaline 4-oxides with dimethyl acetylenedicarboxylate

The reaction of 6-chloro-2-hydrazinoquinoxaline 4-oxide 6 with ethyl 2-(ethoxymethylene)-2-cyanoacetate or (1-ethoxyethylidene)malononitrile gave 2-(5-amino-4-ethoxycarbonylpyrazol-1-yl)-6-chloroquinoxaline 4-oxide 7a or 2-(5-amino-4-cyano-3-methylpyrazol-1-yl)-6-chloroquinoxaline 4-oxide 7b , respectively. The reaction of compound 7a or 7b with dimethyl acetylenedicarboxylate resulted in the 1,3-dipolar cycloaddition reaction and then ring transformation to afford 4-(5-amino-4-ethoxycarbonylpyrazol-1-yl)-8-chloro-1,2,3-trismethoxycarbonylpyrrolo[1,2-α]quinoxaline 8a or 4-(5-amino-4-cyano-3-methylpyrazol-1-yl)-8-chloro-1,2,3-trismethoxycarbonylpyrrolo[1,2-α]quinoxaline 8b , respectively.     

Reaction of methyl 1-bromocycloalkanecarboxylates with zinc and ethyl 5-aryl-3-oxo-2,2-diethylpent-4-enoates

Methyl 1-bromoalkanecarboxylates react with zinc and ethyl 5-aryl-3-oxo-2,2-diethylpent-4-enoates to form ethyl 2-(10-aryl-6-oxo-7-oxaspiro[4.5]dec-8-en-8-yl)-2-ethylbutanoates and ethyl 2-(5-aryl-1-oxo-2-oxaspiro[5.5]undec-3-en-3-yl)-2-ethylbutanoates.     

Reaction of adamantan-2-amine and (adamantan-1-yl)methylamine with methyl 2-(4-allyl-2-methoxyphenoxy)acetate

A reaction of methyl 2-(4-allyl-2-methoxyphenoxy)acetate with adamantan-2-amine and (adamantan-1-yl)methylamine in butanol leads, together with the target amides, to the formation of butyl ester of the corresponding acid, which is resistant to aminolysis.     

1β-Methylcarbapenem intermediates via the thiolysis of a Meldrum's precursor

5-{3-[1-(tert-Butyldimethylsilyloxy)ethyl]-4-oxo-azetidin-2-yl}-2,2,5-trimethyl-[1,3]dioxane-4,6-dione (3) has been submitted to nucleophilic attack with various nucleophiles. Meldrum's moiety transesterification, C4-substitution, β-lactam ring opening and Meldrum's moiety decarboxylation were observed. Reaction of 3 with ethanethiol and dimethylaminopyridine in ethanol quantitatively furnished ethyl 2-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxo-azetidin-2-yl}-thiopropionate as the 1:1 mixture of β (7a) and (8a) diastereoisomers.     

Synthesis and structure of 1-[ω-(3,3-dialkyldiaziridin-1-yl)alkyl]-3,3-dialkyldiaziridines

A method for the synthesis of 1-[ω-(3,3-dialkyldiaziridin-1-yl)alkyl]-3,3-dialkyldiaziridines based on the reaction of ketoxime O-arenesulfonates with alkylenediamines was developed. Diastrereomers (the racemic and meso forms) of 1-[2-(3,3-dimethyldiaziridin-1-yl)ethyl]-3,3-dimethyldiaziridine were isolated. The structure of the meso form was confirmed by X-ray diffraction analysis. Dedicated to Academician V. A. Tartakovsky on his 75th birthday. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1491–1495, August, 2007.     

Synthesis of 2-Mono- and 2,2-Bis[2-(1<Emphasis Type="Italic">H</Emphasis>-tetrazol-5-yl)ethyl] Derivatives of Dipterocarpol

The azidation of 2,2-bis(2-cyanoethyl)-20-hydroxydammar-24-en-3-one afforded new tetrazole derivatives of natural dipterocarpol, 2-(2-cyanoethyl)-2-[2-(1H-tetrazol-5-yl)ethyl]-20-hydroxydammar-24-en- 3-ones, 2,2-bis[2-(1H-tetrazol-5-yl)ethyl]-20-hydroxydammar-24-en-3-one, and 2,2-bis[2-(1H-tetrazol-5-yl)- ethyl]-3-oxo-25,26,27-trinordammaran-(20S),24-olide. The structure of the final and intermediate products was determined by NMR spectroscopy and X-ray analysis.