N,N-Di(prop-2-yn-1-yl)adamantan-1-amines in 1,3-Dipolar Cycloaddition Reactions with Azide-Containing Pharmacophores

Russian Journal of General Chemistry - A synthetic approach to combining pharmacophore ligands with an aminoadamantyl-containing spacer based on a copper-catalyzed alkyne-azide 1,3-dipolar...     

[1,3]-Dipolar cycloaddition of N-aryl sydnones to benzothiophene 1,1-dioxide, 1-cyclopropylprop-2-yn-1-ol and 1-(prop-2-ynyl)-1H-indole

[1,3]-Dipolar cycloadditions of N-aryl sydnones to benzothiophene 1,1-dioxide, 1-cyclopropylprop-2-yn-1-ol and 1-(prop-2-ynyl)indole gave fused pyrazole derivatives when carried out in refluxing toluene. While the first two dipolarophiles gave single regioisomers, this indolic derivative gave mixtures, the ratios of which appeared to be controlled by the phenyl substituents. Their structures were identified in the usual manner, supported by single crystal X-ray diffraction measurements.     

Synthesis of stereo-defined 1,1,4,4-tetrahalo- and 1,1,4,4-mixed-tetrahalo-1,3-butadienes

Stereo-defined 1,1,4,4-tetrahalo- and 1,1,4,4-mixed-tetrahalo-1,3-butadienes were obtained in excellent yields via desilylation-halogenation of their corresponding 1,4-bis(trimethylsilyl)-1,4-dihalo-1,3-dienes, which could be readily prepared from the zirconocene-mediated high-yield and high-regioselective cyclo-dimerization of 1-trimethylsilyl-1-alkynes followed by halogenation. These poly-functionalized gem-dihalodienes are potentially useful building blocks.     

1,3-Dipolar cycloadditions of prop-1-ene-1,3-sultone with nitrile oxides/nitrones

The scope and limitations of dipolar cycloaddition reactions between nitrile oxides/nitrones and prop-1-ene-1,3-sultone have been investigated. A remarkably high degree of regioselectivity and stereoselectivity was observed. The homochiral sultam 8e was synthesized in a four-step reaction sequence starting from the substituted isoxazoline 4e obtained from the cycloaddition. The absolute stereochemistry of this material was assigned by an X-ray crystallographic investigation of the intermediate 7e.     

Novel rearrangement of prop-2-ynyl N-Oxides to hydroxylamine O-allenyl ethers: mechanistic studies

The novel thermolytic rearrangement of prop-2-ynyl N-Oxides to hydroxylamine O-allenyl ethers has been examined by deuterium labeling. Product analysis by gc-eims and by cims has shown the reaction to proceed by a concerted cyclic transition state.     

Reactions of indolylmagnesium bromide with trans-2-phenylcyclopropane-1-carbonyl chloride

Russian Journal of General Chemistry -     

Alkylation of 1-(prop-2-ynyl)piperidine with СН-acids in ihe presence of mercury(II) acetate

General regilarities of the reaction of C-nucleophiles with 1-(prop-2-ynyl)piperidine in the presence of mercuty(II) acetate to form mono-and dicarbonyl derivatives of piperidine and bis[3-(piperidin-1-yl)prop-1-ynyl]mercury. Conditions of these reactions were optimized.     

Alkylation of 3-nitro-1,2,4-triazole with allyl bromide and cyclohexa-1,3-diene in acid medium

Russian Journal of Organic Chemistry -     

Reactions of benzimidazole-2-thiol with N-alkyl-1-aza-1,3-enynes

Reactions of N-alkyl-1-aza-1,3-enynes with benzimidazole-2-thiol in anhydrous dimethylformamide have been studied. The structure of the obtained compounds has been elucidated from the NMR data.     

Synthesis,X-ray structure,and stevens rearrangement of 1,1-di(prop-2-yn-1-yl)-2,5-dihydro-1H-pyrrol-1-ium bromide

1,1-Di(prop-2-yn-1-yl)-2,5-dihydro-1H-Pyrrol-1-ium bromide was obtained with interaction of 3-pyrroline with propargyl bromide and its structure was studied by X-ray analysis. It has been shown that the Stevens rearrangement of obtaining salt leads to the formation of 1-(hexa-4,5-dien-1-yn-3-yl)-2,5-dihydro-1H-pyrrol.     

Unusual reaction of N-(1-adamantylmethyl)-2-hydroxybenzamide potassium salt with allyl bromide

Russian Journal of Organic Chemistry -     

Reaction of 2-(2-Cyanoethyl)-1,1-dimethylhydrazine with Prop-2-ynyl Bromide, 1,3-Dibromopropyne,and Allyl Bromide

The reactions of 2-(2-cyanoethyl)-1,1-dimethylhydrazine with prop-2-ynyl bromide, 1,3-dibromopropyne, and allyl bromide involve alkylation by a tertiary nitrogen atom to form 2-(2-cyanoethyl)-1,1-dimethyl-1-(prop-2-ynyl)-, 1-(3-bromoprop-1-ynyl)-2-(2-cyanoethyl)-1,1-dimethyl-, and 1-allyl-2-(2-cyanoethyl)-1,1-dimethylhydrazinium bromides.     

Reaction of polyfluoroarenesulfonyl bromides with allyl bromide. Synthesis of allyl polyfluoroaryl sulfones

Reactions of polyfluoroarenesulfonyl bromides 4-XC₆F₄SO₂Br (X = F, H, Cl, Br, CF₃) with allyl bromide gave 84–94% of the corresponding allyl polyfluoroaryl sulfones.     

Reaction of allyl bromide with carbonyl compounds mediated by tributylbismuthine [1]

In the presence of tributylbismuthine, allyl bromide was found to react with either aldehydes or ketones to give the corresponding homoallylic alcohols and their allylic ethers in good total yields.