Synthesis of new biheterocycles containing a 1,4-benzodioxane fragment

The reaction of 1,4-benzodioxane-2-carbonyl chloride with 5-(4-aminophenyl)-1,3,4-oxa- and -thiadiazole-2-thiols afforded new biheterocyclic compounds which were converted into the corresponding S-benzyl derivatives by treatment with benzyl chloride. 5-(4-Aroylaminophenyl)-1,3,4-oxa(thia)diazole-2-thiols reacted with 2-bromomethyl-1,4-benzodioxane to give compounds in which the 1,4-benzodioxane nucleus and fivemembered heterocycle are linked through a CH₂S bridge.     

Synthesis and characterization of novel phosphoramidates containing benzimidazole moiety

Novel heterocyclic phosphoramidates were synthesized by a nucleophilic substitution reaction of 2-substitutedbenzimidazoles and diphenyl chlorophosphate (ClPO₃Ph₂) in the presence of potassium hydroxide (KOH) under an argon atmosphere. The structures of the phosphoramidates were characterized by NMR, IR, melting point, and elemental analysis.     

Synthesis of spirocyclic derivatives of azaphenanthrene containing a hydroxy-m-terphenyl fragment

The reaction of 5′-[(2-naphthylamino)methyl]-2′-hydroxy[1,1′:3′,1″]terphenyl with paraformaldehyde and 1,3-cyclohexanedione, methyl 2,2-dimethyl-4,6-dioxocyclohexanecarboxylate, dimedone, furan-2,4(3H,5H)-dione, indan-1,3-dione led to the formation of spiro derivatives of azaphenanthrene.     

Synthesis of unsaturated δ-amino ketones containing a macrocyclic fragment

Conclusions A number of dienic mono--dimethylamino ketones, containing a macrocylic fragment, was synthesized by the condensation of 1,1,3-trimethoxy-3-dimethylaminopropane and-dimethylaminoacrolein acetal aminal with macrocylic ketones. We were unable to obtain polyenic bis-,-dimethylamino ketones, containing a macrocyclic fragment, by this route.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1373–1376, June, 1980.The authors express their gratitude to S. Z. Taits and E. S. Balenkova for supplying the macroeyclic ketones.     

Synthesis of new enantiomeric 1,2-diamines containing a myrtenyl fragment

Some new bi -and tridentate nitrogen-containing chiral ligands were synthesized on the basis of natural monoterpenoids, (+)-and (?)-myrtenals and (+)-myrtenol. A procedure was proposed for the synthesis of unsymmetrical ligands containing terpenoid and o-hydroxyphenyl fragments.     

Synthesis of nitriles containing 3-phenoxyphenyl fragment

Reactions of the aldol-crotonic condensation, acylation of acetonitrile, and addition of amine to the activated double bond of acrylonitrile in the series of diphenyl oxide derivatives are studied. Effective procedures for preparing the nitriles containing diphenyl oxide fragment like 3-(3-phenoxyphenyl)-propenonitrile, 3-(3-phenoxyphenyl)-2-butenonitrile, 3-phenoxybenzoylacetonitrile, 3-(3-phenoxyphenyl)-propionitrile, and 3-phenoxybenzylamino)propionitrile are developed.     

Synthesis and studies of new photochromic spiropyrans containing a formylcoumarin fragment

A computer search for new photoactive compounds among indoline spiropyrans of coumarin series was carried out using DFT B3LYP/6-31G(d,p) method. Based on the data obtained, the spiropyrans containing a formylcoumarin fragment annulated to the 2H-pyran ring and possessing photochromic properties were synthesized. The structure and photochromism of these compounds were studied by ¹H NMR, IR, and UV/Vis spectroscopy. The introduction of a formyl group into the coumarin moiety of spiropyrans led to a bathochromic shift of the long wavelength absorption maxima of merocyanine isomers, as well as to a considerable increase in their lifetime.     

Synthesis and photochromic properties of spiropyrans containing a fused benzopyranone fragment

New spiro compounds of the indole, phthalazine, isobenzofuran, and benzopyran series, containing a fused benzopyranone fragment in the chromene moiety, were synthesized. Indole derivatives were found to exhibit photochromic properties under stationary conditions at 293 K. The thermal stability of merocyanine isomers sharply decreases upon introduction of electron-withdrawing nitro group into the indole fragment and fusion of a benzene ring to the chromene fragment.     

Synthesis of new titanatranes containing organic substituents in the atrane fragment

Titanatrane CpTi(OCH(CH₃)CH₂)₃N (3) was prepared by the reaction of CpTiCl₃ with N(CH₂CH(CH₃)OH)₃ in the presence of triethylamine. The reaction of CpTi(OMe)₃ (8) with N(CH₂CH₂OH)₂(CH₂CHPhOH), erythro-N(CH₂CH₂OH)₂(CHPhCHPhOH), and N(CH₂CH₂OH)₂(CH₂CPh₂OH) gave cyclopentadienyltitanatranes 12–14. Compound 8 reacts with threo-N(CH₂CH₂OH)₂(CHPhCHPhOH) to give a mixture of threo-CpTi(OCH₂CH₂)₂(OCHPhCHPh)N and threo-MeOTi(OCH₂CH₂)₂(OCHPhCHPh)N. Slow hydrolysis of the latter product gave threo-[Ti₃O(OMe){(OCH₂CH₂)₂₋ (OCHPhCHPh)N} ₃]₂, which was studied by X-ray diffraction analysis. The crystal structures of 3 and 12 were also determined by X-ray diffraction analysis. The titanium coordination polyhedron in these complexes is a distorted trigonal bipyramid in which the equatorial positions are occupied by three oxygen atoms and the axial positions contain the N atom and the Cp group. The titanium—nitrogen distances (2.313(2), 2.291(2) Å in two independent molecules of 3 and 2.271(2) Å in compound 12) confirm the presence of Ti←N transannular interaction. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2736–2744, December, 2005.     

Synthesis of new liquid crystalline compounds containing a β-hydroxyketone fragment in the side chain

Liquid crystalline benzoates with a smectic meso phase were synthesized on the basis of 3-hydroxy-1-(4-hydroxyphenyl)-1-octanone by esterification of 4-alkoxybenzoic acids.Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 9, 2004, pp. 1344–1348.Original Russian Text Copyright © 2004 by Bezborodov, Kovganko.     

Synthesis of positively charged lipids containing a 1,3-oxathiolane cycle

Positively charged lipids of the 1,3-oxathiolane series were synthesized by interaction of 2-pentadecyl-5-tosyloxymethyl- or -5-iodomethyl-1,3-oxathiolane with 2-(N,N-dimcthyl-amino)ethanol.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2347–2349, September, 1996.     

Synthesis of 2-substituted isoxazoline and imidazoline,containing a vinylacetyl fragment

The reaction of4-dialkylamino-1-acetyl-1-buten-3-ynes with 1-hydroxy-2-aminoethane and 1,2-diaminoethane was used to synthesize 2-substituted oxazoline and imidazoline, containing a fully enolized vinylacetyl fragment.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1409–1410, October 1992.     

Synthesis of adenine derivatives containing an amino alcohol fragment

The alkylation of adenine and N(in6)-substituted adenine derivatives by 1, 2-dihaloethanes and the production of 9-(2-haloethyl)derivatives of adenine were studied. 1n the reaction of the derivatives with amino alcohols a series of adenine derivatives containing an amino alcohol fragment was synthesized.Latvian Institute of Organic Synthesis, Riga, LV-1006. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 386–390, March, 1996. Original article submitted March 7, 1995.     

Synthesis and oxidation of sulfides containing an isocyanurate fragment

The reaction of 1-(ω-haloalkyl)-3,5-dimethylisocyanurates with sodium salt of methyl thioglycolate afforded the corresponding 1-[ω-(methoxycarbonylmethylthio)alkyl]-3,5-dimethylisocyanurates, the oxidation of which with the system 34% aqueous H₂O₂-0.2 M NaHCO₃-Mn^II leads to the corresponding sulfones. The oxidation of these compounds with 34% aq. H₂O₂ in Ac₂O gives alternative products, viz., sulfones, sulfoxides, or α-acyloxy sulfides, depending on the temperature and number of methylene groups between the isocyanurate fragment and the sulfur atom.     

Synthesis and properties of aliphatic oligoamides containing methionine fragment

Oligoamides were prepared from dimerized fatty acid, hexamethylenediamine, and an amino acid (methionine). The effect of methionine on the course of polycondensation and properties of the reaction products was examined. New thermoplastic adhesive compounds based on these products were developed.     

Synthesis of nitroso- and aminopyrazoles containing an adamantane fragment

Russian Journal of Organic Chemistry -     

Synthesis of 1,2-azaphospholanes containing an amino acid fragment

2-Oxo-1,2-azaphospholanes and 1,2-azaphospholanium salts containing an amino acid fragment were synthesized by intramolecular P-alkylation of N-3-chloropropyl-substituted tricoordinate phosphorus amides. Hydrolysis of 2-oxo-1,2-azaphospholanes at the P-N bond gives rise to γ-aminopropylphosphonic acid derivatives. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2557–2562, November, 2005.     

Synthesis and complex formation of spirobenzopyranindolines containing rhodamine fragment

The interaction of 7-hydroxy-6-formyl-substituted spiropyrans and Rhodamine B aminoethylamide has afforded spirobenzopyrans containing rhodamine fragment bound to the benzopyran part via the methyleneaminoethyl spacer. The prepared spiropyrans exist in the spiropyran-spirolactam form in the acetone solution and exhibit weak photochromism at 283 K. The addition of Cd, Co, Ni, and Zn perchlorates to the spiropyrans solution results in the coloration due to the complex formation. The composition and stability of the complexes has been determined by means of spectrophotometry.