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.     

The Synthesis and Reactions of 1-(2-Propynyl)pyidinium Salts

The synthesis of 1-(2-propynyl)pyridinium salts 3 described. Compounds 3 react with a second pyridine molecule, in the presence of the corresponding hydrochloride, to form products of type 4, Certain bases cause the 1-(2-propynyl)pyridinium salts 3 to rearrange into 1-propadienylpyridinium salts. 5 . Diethylamine converts compounds 3 into 1-acetonylpyridinium salts 8 . Moreover, treatment of 3 or 5 with sodium methoxide gives enol ether sof type 9, which can be hydrolyzed to teh ketones 8 . Addition of bromine to some of teh unsaturated compounds is also reported.     

Regioselective Reactions of Pyridine-2-sulfenyl Bromide with Vinyl and Allyl Ethers

Russian Journal of General Chemistry - Annulation reactions of pyridine-2-sulfenyl bromide with vinyl and allyl ethers proceeded regioselectively, but with opposite regiochemistry. Reactions with...     

2-[2-(2,3-Dihydrobenzimidazolylidene)]- and 2-[2-(2,3-Dihydropyrido[2,3-d]imidazolylidene)]-5,5-dimethyl-1,3-cyclohexanediones

The reaction of 2-aminocarbonyl-5,5-dimethyl-1,3-cyclohexanedione with 2,3-diaminopyridine, 1,2-phenylenediamine (and its 4-methyl, 4-nitro, 4-carboxy, and 4-benzoyl derivatives), and 3,3-diaminobenzidine gave the corresponding 2-[2-(2,3-dihydrobenzimidazolylidene)]- and 2-[2-(2,3-dihydropyrido[2,3-d]imidazolylidene)]-5,5-dimethyl-1,3-cyclohexanediones. Their structure was confirmed by ¹H NMR spectroscopic data and X-ray analysis.     

Reactions of 3-[N-chloroacetylamino-N-(4-nitrophenyl)]-2-formylindole with alkylamines

The reactions of 3-[N-chloracetylamino-N-(4-nitrophenyl)]-2-formylindole (1a) with 2-(N, N-dialkylamino)ethylamines afford complex condensation products 7b,c consisting of two similar but not identical diazepinoindole fragments. For the reaction of compound 1a with 3-(N,N-diethylamino)propylamine, the process occurs in a different manner, and the predominant product is 4-ethylaminopropyl-1-(4-nitrophenyl)-2-oxo-1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole hydrocloride (14). Two routes of these unexpected transformations were proposed. The structures of the synthesized products were proved by the ¹sH and ¹³C NMR, HMBC, and HSQC (direct proton-carbon correlation) spectra. Dedicated to Academician V. A. Tartakovsky on the occasion of his 75th birthday. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1536–1542, August, 2007.     

Products of the Reactions of 1-Aroyl-2,2-dimethylhydrazines with Propargyl and Allyl Bromides

1-Aroyl-2,2-dimethylhydrazines react with propargyl and allyl bromides to form, respectively, 1,1-dimethyl-1-(2-propyn-1-yl)- and 1,1-dimethyl-1-(2-propen-1-yl)-2-aroylhydrazinium bromides. Treatment of these compounds with an NaOH solution yielded, respectively, N-[dimethyl(2-propyn-1-yl)ammonio]- and N-[dimethyl(2-propen-1-yl)ammonio]aroylimides.     

Lipase mediated enantiomer and diastereomer separation of 2,2′-[1,2- and 1,3-phenylenebis(oxy)]dicyclohexanols

Separation of diastereomeric and enantiomeric mixtures of 2,2′-[1,2- and 1,3-phenylenebis(oxy)]dicyclohexanols rac-3a and meso-3a, and rac-3b and meso-3b—resulting from the reactions of pyrocatechol 1a and resorcinol 1b with cyclohexene oxide 2—were performed using acetylation catalyzed by the highly stereoselective Candida antarctica lipase B (Novozym 435). The absolute configurations of the resulting diols (S,S,S,S)-3a,b, monoacetates (R,R,S,S)-4a,b and diacetates (R,R,R,R)-5a,b were assigned on the basis of the steric analogy to the acetylation of racemic trans-2-phenoxycyclohexanol rac-6 with the same enzyme resulting in the known acetate (−)-(R,R)-7.     

Reactions of (4E)-3-Arylamino-4-(hydroxyimino)naphthalen-1(4H)-ones and (4E)-2-[Arylamino(alkylamino)]-4-(hydroxyimino)naphthalen-1(4H)-ones with 2,2-Dihydroxyindane-1,3-dione

Russian Journal of Organic Chemistry - The reactions of 3-arylamino-1,4-naphthoquinone-4-oximes with 2,2-dihydroxyindane-1,3-dione proceed without involving the oxime group and lead to...     

Efficient Synthesis of 1-(2-Propynyl)pyrrole

Russian Journal of Organic Chemistry -     

Reactions of 2-(2-Furyl)-1,3-dioxacycloalkanes with Triethylsilane

Russian Journal of Organic Chemistry -     

Synthesis and Crystal Structure of 2,2-Dimethyl-4-[1H-（ 1,2,4-triazolyl）]-4- [ 1H-benzotriazolyl]-3- butanone[t-BuCOCH（C2H2N3）（C6H4N3）]

1 INTRODUCTION Triazole nuclei appear frequently in the structures of various natural products and biologically active compounds, notably thiamine (vitamin B), peni- cillins, antibiotics such as micrococcin[1], and many metabolic products of fungi and p…     

Reactions of Tricyclo[4.1.0.02,7]heptane and 1-Methyltricyclo[4.1.0.02,7]heptane with 2-Bromoethanesulfonyl Bromide

Russian Journal of Organic Chemistry - 2-Bromoethanesulfonyl bromide reacts with tricyclo[4.1.0.02,7]heptane and 1-methyltricyclo[4.1.0.02,7]heptane according to a radical mechanism to give...     

Synthesis of 3-[2-(1,3-butadienyl)]-1H-indoles en route to murrapanine analogue

A three-step procedure has been developed for the synthesis of 3-[2-(1,3-butadienyl)]-1H-indoles. TBAF was proved to be an effective reagent for dehydrobromination and carbomethoxy deprotection in one step to give 3-[2-(1,3-butadienyl)]-1H-indoles from the corresponding bromo-derivatives. Suitably substituted indolyl-1,3-butadiene has been successfully applied to prepare murrapanine analogue via Diels-Alder reaction.     

Unexpected Regioselective Reactions of 2-(Bromomethyl)-1,3-thiaselenole with 1-Methyl-1H-imidazol-2-thiol,Accompanied by Rearrangements

Russian Journal of Organic Chemistry - The previously unknown regioselective reactions of 2-(bromomethyl)-1,3-thiaselenole with 1-methyl-1H-imidazol-2-thiol were used to develop efficient synthetic...