Reactions of 1-[Benzoyl(2-hetaroyl)]-2,2-dimethyhydrazines with 1,3-Dibromopropyne, 2-Propynyl Bromide,and Allyl Bromide

Reactions of 1-[benzoyl(2-hetaroyl)]-2,2-dimethyhydrazines with 1,3-dibromopropyne in MeOH at 50°C afforded 2-phenyl(heteryl)-6-bromomethylidene-4,4-dimethyl-5H-1,3,4-oxadiazinium bromides. Reactions of 1-[benzoyl(2-hetaroyl)]-2,2-dimethyhydrazines with propargyl bromide and allyl bromide gave rise to 1,1-dimethyl-1-(2-propyn-1-yl)- and 1,1-dimethyl-1-(2-propen-1-yl)-2-benzoyl(hetaroyl)hydrazinium bromides. On treating these compounds with NaOH solution the corresponding imides were obtained.     

Catecholborane Reductive Cleavage of Allyl and Propargyl Acetals and Ketals: A Simple Route to Allyl and Prop-2-ynyl Ethers

the chemoselective conversion of allyl and prop-2-ynyl acetals as well as ketals by reductive cleavage with catecholborane into the corresponding allyl and prop-2-ynyl ethers is described.     

Synthesis of 1,3,4-Oxadiazinium Bromides from 1,1-Dimethylhydrazine Derivatives and 1,3-Dibromopropyne

2-Aryl(heteryl, dimethylamino)-6-bromomethylidene-4,4-dimethyl-5H-1,3,4-oxadiazinium bromides were prepared in good yields by the reactions of 1-aroyl(heteroyl)-2,2-dimethylhydrazines and 1,1,4,4-tetramethylsemicarbazide with 1,3-dibromopropyne in MeOH or MeCN at 20–50°C.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 3, 2005, pp. 473–475.Original Russian Text Copyright © 2005 by Nakhmanovich, Elokhina, Larina, Abramova, Lopyrev.     

Reaction of dichloro- and dibromocarbenes with 2-(vinyloxy)-1,3-butadiene

Conclusions A disubstituted multiple bond has the greatest activity in the reaction of 2-(vinyloxy)-1,3-butadiene with dichloro- and dibromocarbenes. The vinyloxy group stabilizes the transition state less effectively than the alkyl or aryl substituent.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1286–1290, June, 1979.     

Reaction of phenoxazine and phenothiazine with 1,1-dicyano-2-(trifluoromethyl)ethylenes

1,1-Dicyano-2,2-bis(triflüoronietliyl)etliylene alkylates phenoxazine and phenothiazine at 20 °C at thepara-position relative to the N atom.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 1026–1027, April, 1996.     

Reaction of (R)-(-)-2-aminomethylpyrrolidine(1,1-cyclobutanedicarboxylato)platinum( II) with guanosine

The reaction of a new antitumor platinum complex, (R)-(-)-2-aminomethylpyrrolidine(1,1-cyclobutanedicarboxylato++ +)platinum(II) (1) with guanosine at room temperature in an aqueous solution was followed by proton nuclear magnetic resonance (1H-NMR) spectroscopy and high performance liquid chromatography (HPLC) at intervals. Both techniques showed that a new compound was formed by displacement of the 1,1-cyclobutanedicarboxylate moiety of 1 with two guanosines, and its 1H-NMR spectrum and HPLC chromatogram were proved to be identical with those of [(R)-(-)-2-aminomethylpyrrolidine]bis(N7-guanosine)platinum(II) (2), which was obtained upon successive treatment of (R)-(-)-2-aminomethylpyrrolidinedichloroplatinum(II) (3) with AgNO3 and 2 mol eq of guanosine in water. The binding sites of the platinum to the two guanosine moieties in 2 were confirmed by the pH dependence of the two G-H8 signals.     

Indium-Mediated Michael Addition of Allyl Bromide to 1,1-Dicyano-2-arylethenes in Aqueous Media

Indium-mediated addition of allyl bromide to 1,1-dicyano-2-arylethenes gives Michael addition products in aqueous media with good yields. The reaction need neither any activation nor in inert atmosphere.     

Synthesis of 1-[1-bromo-2-benzoyl(2-thenoyl)vinyl]-1,1-dimethylhydrazinium bromides from 1-bromo-2-benzoyl(2-thenoyl)acetylenes and 1,1-dimethylhydrazine

1-[1-Bromo-2-benzoyl(2-thenoyl)vinyl]-1,1-dimethylhydrazinium bromides were synthesized by the reactions of 1-aroyl-2-bromoacetylenes withN,N-dimethylhydrazine in acetonitrile at 20°C. The structure of 1-(2-benzoyl-1-bromovinyl)-1,1-dimethylhydrazinium bromide was established by X-ray diffraction analysis. Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 8, pp. 1536–1538, August, 1999.     

Reaction of 4-(N,N-Dimethylaminophenyl)magnesium Bromide with Palladium Tetrakis(triphenylphosphine)

The influence of reaction conditions on catalyzed by Pd(PPh₃)₄ cross-coupling of 4-N,N-dimethylaminophenylmagnesium bromide with 4-bromobenzonitrile in tetrahydrofuran was investigated. The yield of the product of the catalytic process, 4-N,N-dimethylamino-4'-cyanobiphenyl, and of the main product of noncatalytic process, 4-N,N-dimethylaminophenyl 4'-bromophenyl ketone, is mainly governed by the order of introduction of reagents and catalyst into the reaction zone. Experimental observations and analysis of side products suggested conclusions on the processes resulting in deactivation of the catalyst.     

[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.