Tertiary Acetylenic Alcohols and Peroxides Derived from 4,4'-Bis(dimethylamino)benzophenone (Michler's Ketone)

Tertiary acetylenic alcohols were obtained by treatment of 4'4'-bis(dimethylamino)benzophenonewith 1-alkynyl-, 2-phenylehynyl, as well as lithium tert-alkylperoxyacetylides.     

Synthesis of 2-(2-Naphthyl)quinolines from Z-3-(2-Naphthyl)-3-chloro-2-propenal

By reaction of Z-3-(2-naphthyl)-3-chloro-2-propenal and aromatic amines 1-(2-naphthyl)-3-iminoaryl-1-propenylarylamines were prepared which at heating in the glacial acetic acid afforded the corresponding 2-(2-naphthyl)quinolines.     

Acetylenic Peroxides Derived from 4,4'-Biphenyldicarboxylic Acids

Lithium peroxyacetylides were reacted with Paraform to obtain lithium peroxyalcoholates. The latter react with 4,4'-biphenyldicarboxylic and 2,2'-sulfonyl-4,4'-biphenyldicarboxylic dichlorides, yielding peroxy-containing esters. Lithium peroxyacetylides react with 4,4'-biphenyldicarboxylic and 2-methoxy- and 2,2'-sulfonyl-4,4'-biphenyldicarboxylic acids to form acetylenic biphenyldihydroxytetraperoxides.     

(Z)-3-chloro-3-(2-naphthyl)prop-2-enal in the synthesis of naphthyl-substituted thiophene and quinolines

2-(2-Naphthyl)thiophene was synthesized by condensation of 3-chloro-3-(2-naphthyl)prop-2-enal with sulfanylacetic acid. A modified procedure was proposed for the synthesis of 2-(2-naphthyl)-and 2-(2-naphthyl)-6-nitroquinolines from 3-chloro-3-(2-naphthyl)prop-2-enal.     

Peroxy-containing Tertiary Acetylenic Alcohols Derived from Cycloheptanone,Cyclododecanone, and (-)-R-Carvone

A series of peroxy-containing tertiary acetylenic alcohols were obtained by reactions of lithium peroxyacetylides with cycloheptanone, cyclododecanone, and (-)-R-carvone. Thermal stability of the products was estimated by thermal analysis and quantum-chemical calculations.     

Peroxy-Containing Acetylenic Alcohols and Ethers Derived from 4-Methoxybenzophenone and 1- and 2-Acetonaphthones

A procedure was suggested for the synthesis of 2,5-dimethyl-2-tert-alkylperoxy-5-lithiooxy-5-methyl(phenyl)-5-naphthyl(aryl)alk-3-ynes by the reactions of the corresponding monosubstituted peroxyalkynes with butyllithium, followed by the reactions of the resulting lithium peroxy acetylenides with 4-methoxybenzophenone and 1- and 2-acetonaphthones. Lithium peroxy alcoholates are hydrolyzed with water to form peroxy-containing alcohols and react with methyl iodide in the presence of dimethyl sulfoxide to form the corresponding 2,5-dimethyl-2-tert-alkylperoxy-5-methoxy-5-methyl(phenyl)-5-naphthyl(aryl)alk-3-ynes. The thermal stability of the peroxides prepared was evaluated by thermal analysis.     

Nucleophilic Vinylic Substitutions of (E)- and (Z)-Ethyl 3-Aryl-3-chloro-2-cyanopropenoates with Primary and Secondary Amines

Some new (Z)-ethyl 3-amino-3-aryl-2-cyanopropenoates have been prepared in good yields by reacting (E)- and (Z)-ethyl 3-aryl-3-chloro-2-cyanopropenoates with primary and secondary amines. The (Z)-isomers were exclusively formed.although the starting material consisted of a mixture of (E)- and (Z)-isomers (≈ 1:1)     

Synthesis of 1-(2-naphthyl)dihydro- and 1-(2-naphthyl)-2-thiodihydrouracils and their transformations

1-(2-Naphthyl)dihydro- and 1-(2-naphthyl)-2-thiodihydrouracils were obtained from N-(2-naphthyl)--alanine derivatives. The thiodihydrouracil was converted to a dihydrouracil. Bromination of 1-(2-naphthyl)dihydrouracil gave (1-bromonaphthyl)dihydrouracil. 1-(2-Naphthyl)-2-oxo-, 1-(2-naphthyl)-2-thio-. and 1-(1-bromo-2-naphthyl)-2-oxohexahydro-pyrimidines were obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii. No. 12, pp. 1695–1697, December, 1971.     

Acetylenic Hydroperoxides Derived from 2e-Methyldecahydroquinolin-4-one

2e-Methyldecahydroquinolin-4-one was reacted with lithium tert-alkylperoxy acetylides to prepare 4-hydroxy-2e-methyl-4-(2-methyl-2-tert-alkylperoxy-1-butyn-4-yl)decahydroquinolines. The latter readily react with carboxylic acids and methyl iodide, affording the corresponding salts.     

Reaction of 2-(4-Arylthiazol-2-yl)-4-chloro-3-oxobutyronitriles with Secondary Aliphatic Amines

We have obtained 2-(4-arylthiazol-2-yl)-4-chloro-3-oxobutyronitriles by acylation of 4-aryl-2-cyanomethylthiazoles with -chloroacetyl chloride. We have studied their reaction with secondary aliphatic amines, leading to formation of 4-dialkylamino-2-(4-arylthiazol-2-yl)-3-oxobutyronitriles, and also intramolecular alkylation with formation of 3-aryl-7-cyano-6(5H)-oxopyrrolo[2,1-b]thiazoles. We have determined some aspects of the tautomerism of the synthesized compounds.     

Pyrroles from ketoximes and acetylene. 23. 2-(1-naphthyl)- and 2-(2-naphthyl)pyrroles and their 1-vinyl derivatives

2-(1-Naphthyl)- and 2-(2-naphthyl)pyrroles and their 1-vinyl derivatives were synthesized in 22–64% yields by the reaction of 1- and 2-acetylnaphthalene oximes with acetylene at both atmospheric pressure and elevated pressures in an alkali metal hydroxide-dimethyl sulfoxide system.See [1] for communication 22.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1351–1353, October, 1982.     

1-benzoyl-2-(2-naphthyl)-selenourea

During our synthesis of N-benzoyl-N'-aryl selenourea derivatives, we isolated the title compound. One of them was selected optically for the diffraction study. The crystal belongs to the Monoclinic space group P21/n, Mr = 353.27, a = 11.073(1)A, b = 5.745(1) A, c = 24.356(5) A, β= 92.10 (1) °, V= 1548.3 (4) A3, Z = 4, Dx=1.515 Mg/m3, λ (Mo Kα )=0.71073 A, θ = 1.67-25, μ= 2.428 mm-1 , T = 296 (2) K.View of the molecule showing the labeling of the non-H atoms are described as:The selenourea and thiourea have analogous structure, a few literatures have reported the crystal of N-benzoyl-N'-aryl thiourea derivative1,2. In the reported crystal structure of N-benzoyl-N'-aryl thiourea derivative, there is a intermolecular hydrogen bond between the carbonyl O and H atom on N', in each -C(O)-NH-N'H- moiety, forming a planar six-membered ring. In this title compound,[2.654(2)A], C (8), N (1) and C (7)l.In the crystal structure of N-benzoy-N'-aryl thiourea derivative, there have a two dimensional With the intramolecular hydrogen bond [2.654(2)A] they form the planar four-membered ring between every molecular. The atom of Se dose not link the moleculars like the S atom of N-benzoyl-N'-aryl thiourea derivative, and it is only out of six-membered ring, which forms by N (2)H…O, C (8), N (1) and C (7).