Synthesis and Extractive Power of Polycyclic Pyrimidine Derivatives

A procedure was developed for synthesis of polycyclic pyrimidine derivatives by the reaction of 2,2'-dichlorodicyclohexyl sulfide with uracil, 6-methyluracil, or 5-fluorouracil in the presence of K₂CO₃, followed by oxidation of the resulting products with sodium metaperiodate and hydrogen peroxide. Two of the synthesized compounds were tested in extraction of Ir(IV) from hydrochloric acid solutions.     

Synthesis of derivatives of <Emphasis Type="Italic">o</Emphasis>-aminoacetophenone and <Emphasis Type="Italic">o</Emphasis>-aminobenzyl alcohol

Oxidation of 2′-hydroxy-8-methylspiro[4H-benz-1,3-oxazin-2-one-6,1′-cyclopentane] or N-mesyl-2-(cyclopent-1-en-1-yl)-6-methylaniline provided the corresponding ketones. The rearrangement of these ketones oximes under treatment with thionyl chloride gave rise to nitriles of 5-(2-amino-3-methylphenyl)-5-oxopentanoic or 5-(2-methanesulfamido-3-methylphenyl)-5-hydroxypentanoic acids. By heating 5-(2-acetylamido-3-methylphenyl)-5-oxopentanoic acid with LiH in THF3-(2,8-dimethylquinol-4-on-3-yl)propanoic acid was obtained.     

Synthesis of indolines and tetrahydroquinolines fromortho-(alk-2-enyl)anilines

Intramolecular cyclization ofo-alkenylanilines was studied. Heating ofo-(cyclopent-2-en-1-yl) arylammonium chlorides at 200–220 °C yields cyclopenta[b]indolines as the main reaction products. Cyclization of 4-methyl-2-(pent-3-en-2-yl)aniline under the same conditions gave a mixture of indolines and tetrahydroquinolines. An alk-1-enylarylamine containing a vinylic double bond does not form cyclization products on the nitrogen atom. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 975–978, May, 1999.     

Synthesis of 3-substituted cyclopenta[b]indoles

When reacting with I₂, 2-(cyclopent-2-enyl)anilines undergo cyclization into 3-iodo-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles in high yields. The minor reaction products were 3,5- or 3,7-diiodoindolines. Ammonolysis of 3-iodo-5-methyl-1,2,3,3a,4,8b-hexahydro-cyclopenta[b]indole or itsN-chloroacetyl derivative results in 3-amino-5-methyl-1,2,3,3a,48b-hexahydro- and 5-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles. Published inIzvestiya Akademii Nauk. Seriya Khimischeskaya, No. 10, pp. 1789–1793, October, 2000.     

Amidines: synthesis from o-alkenylanilines and cyclization in polyphosphoric acid

Condensation of 2-[(E)-pent-3-en-2-yl]-4-, 2-[(E)-pent-2-en-2-yl]-4-, or 2-(cyclopent-1-enyl)-6-methylaniline with 1-chloro-1-(N-methylimino)- or 1-chloro-1-(N-phenylimino)ethane affords the corresponding amidines. Cyclization of the N-methylimino derivatives in polyphosphoric acid gives 3,4-dihydroquinazolines in high yields.     

Synthesis of N-(o- and p-Alkenylphenyl)-Substituted Quinazolin-4-ones

Alkenylphenyl-substituted quinazolinones were prepared by reactions of 2-methyl-4H-3,1-benzoxazin-4-one with o- and p-alkenylanilines.     

Claisen amino rearrangement as a method for synthesis of C-cycloalkenylanilines

Conclusions The reaction of 3-chlorocycloalkenes with excess aromatic amine leads to o-(2-cycloalkenyl)-substituted aromatic amines.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2160–2162, September, 1982.     

Cyclization of N-(2-cyclopent-1-en-1-ylphenyl)benzamides in solution and under mass-spectrometric conditions

The cyclization has been studied of N-(2-cyclopent-1-en-1-ylphenyl)benzamides into the corresponding 3,1-benzoxazines by the action of gaseous hydrogen chloride, trifluoroacetic acid, or bromine, and also under conditions of electron impact in the gas phase. A scheme is proposed for the fragmentation of the molecular ions of the products obtained.