- Method development for the determination of 1,1-dimethylhydrazine by the high-performance liquid chromatography–mass spectrometry technique
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Unsymmetrical dimethyl hydrazine is highly toxic, carcinogenic compound, widely used for organic synthesis and drug development. Therefore, due to its high reactivity, direct analysis is problematic. Current study proposes to use derivatization reaction t
- Susinskis, Igors,Mekss, Peteris,Hmelnickis, Juris
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p. 352 - 359
(2018/07/31)
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- Copper-Catalyzed Oxidative Cleavage of Electron-Rich Olefins in Water at Room Temperature
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A copper-catalyzed oxidative cleavage of electron-rich olefins into their corresponding carbonyl derivatives is described as an alternative to ozonolysis. The scope includes various precursors to aryl ketone derivatives, as well as oxidations of enol ethers bearing atypical alkyl and dialkyl substitution, the first of their kind among such metal catalyzed alkene cleavage reactions. The use of an inexpensive copper salt, room temperature conditions, an aerobic atmosphere, and water as the global reaction medium highlight the green features of this new method. Associated mechanistic investigations are also presented.
- Lippincott, Daniel J.,Trejo-Soto, Pedro J.,Gallou, Fabrice,Lipshutz, Bruce H.
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supporting information
p. 5094 - 5097
(2018/09/13)
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- Stereoselective divergent synthesis of 1,2-aminoalcohol-containing heterocycles from a common chiral nonracemic building block
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γ-N,N-Dibenzylamino-β-hydroxysulfoxide 1 proved to be an excellent chiral building block for the synthesis of a range of 1,2-amino alcohol-containing heterocycles. Thus, 1 was converted into 4,5-disubstuted oxazolidin-2-one 4 and aminoepoxides 2 and 3. Aminoepoxide 2 proved to be an excellent precursor to access oxazolidin-2-one 5 and azetidin-3-ol 6. Finally, 2 was used as a key intermediate that allowed the development of a divergent strategy to access cis-2-methyl-6-substituted piperidin-3-ol alkaloids. (+)-Deoxocassine 7 and a C-6 ethyl analogue 8 were prepared to illustrate this approach and to demonstrate that this strategy should be adaptable to the production of other members of this alkaloid family.
- Géant, Pierre-Yves,Grenet, Erwann,Martínez, Jean,Salom-Roig, Xavier J.
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- Chromatographic component of identification of the transformation products of 1,1-dimethylhydrazine in the presence of sulfur
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The gas-chromatographic retention indices of the products of 1,1-dimethylhydrazine transformations in the presence of sulfur allows one to confirm and, in ceratin cases, make more exact the results of their gas chromatography-mass spectrometry identificat
- Zenkevich,Ul'Yanov,Golub,Buryak
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p. 1106 - 1114
(2014/08/05)
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- Retinoids and related compounds. Part 19. Syntheses of 9E- and 9Z-locked retinoic acid analogues and their transcriptional activities as ligands for retinoic acid receptors and retinoid X receptors
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Novel retinoic acid (RA) analogues, 9E-locked-RA 3 and 9Z-locked RA 4, have been synthesized in order to prohibit geometrical isomerization at the C(9)-C(10) double bond when these ligands interact with the retinoic acid receptor (RAR) and retinoid X rece
- Katsuta, Yuko,Aoyama, Yukiko,Osone, Hisa,Wada, Akimori,Ito, Masayoshi
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p. 1405 - 1410
(2007/10/03)
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- REACTIONS OF 1,1-DIALKYLDIAZENIUM SALTS WITH KETONE ETHYLHYDRAZONES
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By reaction of dialkyldiazenium salts with ketone ethylhydrazones, we prepared and characterized 3,3-disubstituted 3,4-dihydroformazans for the first time.The composition of the reaction mixtures indicates a lower (as compared with aldehyde hydrazones) reactivity of ketone hydrazones.
- Kuznetsov, M. A.,Kuznetsova, L. M.,Zasukhina, E. A.
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p. 1363 - 1366
(2007/10/02)
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- Synthesis of (R)-2,3-Dihydro-2,5-dimethyl-2-isopropylfuran
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The synthesis of (R)-2,3-dihydro-2,5-dimethyl-2-isopropylfuran (1), an insect pheromone, via a 1,3-oxathiane is reported.Key steps are the preparation of (S)-2,3-dimethylbutane-1,2-diol (7) from isobutyryloxathiane 5 and reaction of lithiated acetone dimethylhydrazone with tosylated diol 8.NMR spectra of the key tautomeric precursors, 2/2'/3, to 1 have been analyzed in detail, and the enantiomeric excess of these precursors was determined by a chiral shift 13C NMR experiment.
- Bai, Xu,Eliel, Ernest L.
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p. 2086 - 2089
(2007/10/02)
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- Regio-, Diastereo-, and Enantioselective Synthesis of vic-Diols via α-Silyl Ketones According to the SAMP/RAMP Hydrazone Method
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α-Silylated ketones 5 or 10 of high enantiomeric purity (ee>=90percent) are easily available by silylation or silylation/alkylation of ketones 1 or 6, resp., according to the SAMP/RAMP hydrazone method.Reduction of 5 or 10 with L-selectride, followed by oxidative cleavage of the C-Si bond, leads to vic-diols 11-13 with high diastereoselectivity (de>=90percent) and without racemization.The stereoselectivity of the reduction depends on the structure of the α-silyl ketones 5 or 10, the reducing reagents, and the solvents used.Key Words: Ketones, α-silyl / vic-Diols, diastereo- and enantioselective synthesis / SAMP/RAMP Hydrazones / L-Selectride reductions
- Enders, Dieter,Nakai, Shiro
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p. 219 - 226
(2007/10/02)
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- Synthesis of spiroacetal pheromones via metalated hydrazones
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The synthesis of simple alkyl substituted spiroacetals by α,α'-alkylation of metalated acetone dimethylhydrazone with appropriate electrophiles and subsequent acid catalyzed cleavage and ring closure of the products is described.
- Enders,Dahmen,Dederichs,Gatzweiler,Weuster
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p. 1013 - 1019
(2007/10/02)
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- Synthesis of β-lactams via cycloaddition of hydrazones with phenoxyketene
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Phenoxyketene is capable of annelating the disubstituted hydrazones to afford stereoselectivity cis-monocyclic β-lactams with a 1-amino functionality. The ease of cycloaddition is governed by substitutents on the azomethine carbon as well as on the hydraz
- Sharma,Pandhi
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p. 2196 - 2200
(2007/10/02)
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- Selective Cleavage of Dimethylhydrazones to the Carbonyl Compounds Using Silica Gel and its Application in the Synthesis of (Z)-9-Tetradecenyl Acetate
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A new method for the selective hydrolytic cleavage of dimethylhydrazones consists of treatment of the hydrazones with silica gel (pH 6.80) in wet tetrahydrofuran.Utilizing this method as one of the key steps, (Z)-9-tetradecenyl acetate, the pheromone of Spodoptera frugiperda, was synthesized.
- Mitra, R. B.,Reddy, G. Bhaskar
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p. 694 - 698
(2007/10/02)
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- A Convenient Synthesis of Diketones via Alkylation of Alkyl Methyl Ketone Dimethylhydrazones
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Symmetrical diketones were prepared by the reaction of the lithium salts of alkyl methyl metone dimethylhydrazones with dibromoalkanes.
- Yamashita, Masakazu,Matsumiya, Kaoru,Morimoto, Hiroko,Suemitsu, Rikisaku
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p. 1668 - 1670
(2007/10/02)
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- Simple Synthesis of (Z)-12-Nonadecen-9-one, (Z)-13-Icosen-10-one, the Sex Pheromone of Peach Fruit Moth, and (Z)-5-Undecen-2-one, a Biologically Active Molecule from the Pedal Gland of the Bontebok
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A simple and convenient synthesis of (Z)-12-nonadecen-9-one, (Z)-13-icosen-10-one, the sex pheromone of the peach fruit moth, and (Z)-undecen-2-one, the pheromone from the pedal gland of the bontebok, is described.These pheromones were readily synthesized using succesive alkylation of acetone dimethylhydrazone in one-pot.
- Yamashita, Masakazu,Matsumiya, Kaoru,Murakami, Kotomi,Suemitsu, Rikisaku
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p. 3368 - 3370
(2007/10/02)
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- Reactions with Monohydrazones of Dicarbonyl Compounds, X. 2-(Dimethylhydrazono)propanal as a Reagent for the Synthesis of 1,4-Diketones
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Monohydrazones 7 of unsaturated 1,4-diketones can be prepared by the reaction of methylene-active ketones 1a-x with 2-(dimethylhydrazono)propanal (5a).From these products unsaturated (8) and saturated 1,4-diketones (9) are obtained in high yield.Reduction
- Mayring, Lothar,Severin, Theodor
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p. 3863 - 3877
(2007/10/02)
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