- Chemoselective Mono- And Difluorination of 1,3-Dicarbonyl Compounds
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By altering the amount of Selectfluor, the highly selective mono- and difluorination of 1,3-dicarbonyl compounds has been achieved, affording a variety of 2-fluoro- and 2,2-difluoro-1,3-dicarbonyl compounds in good to excellent yields. The reaction can be readily performed in aqueous media without any catalyst and base, which features practical and convenient fluorination. Importantly, a gram-scale reaction, transformation of 2-fluoro-1,3-diphenylpropane-1,3-dione to 4-fluoro-1,3,5-triphenyl-1H-pyrazole, and chlorination and bromination of 1,3-dicarbonyl compounds are realized to further exhibit its synthetic utility.
- Cui, Ying,Jiao, Jingchao,Ma, Xiantao,Rao, Weihao,Tang, Lin,Yang, Zhen,Zhou, Qiuju,Zhou, Yuqiang,Zou, Guodong
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- A convenient method for reduction dehalogenation of α-halocarbonyl compounds using benzenethiol in K+/CH3CN system
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Benzenethiol, as a reductive agent for the dehalogenation of various α-halocarbonyl compounds, is investigated in the K+/CH3CN system. The reaction affords the reduced compounds in high yields under mild reaction conditions, especially α-chlorocarbonyl compounds. Furthermore, the reaction performed under ultrasonic irradiation greatly shortens the reaction time.
- Dong, Wei-Li,Cai, Wen-Xi,Wu, Rui,Li, Zheng-Ming,Zhao, Wei-Guang,Liu, Xing-Hai
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p. 980 - 983
(2016/07/06)
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- Divergent synthesis of α,α-dihaloamides through α,α-dihalogenation of β-oxo amides by using N-halosuccinimides
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An efficient and divergent one-pot synthesis of α,α- dihaloamides from readily available β-oxo amides based on the selection of reaction conditions is reported. α,α-Dihalo-β-oxo amides were produced by treating β-oxo amides with N-chlorosuccinimide (NCS) or N-bromosuccinimide (NBS) in water at room temperature, whereas α,α-dihaloacetamides were synthesized by subjecting β-oxo amides to NCS or NBS in ethanol under reflux. A divergent synthesis of α,α-dihalo-β-oxo amides and α,α-dihaloacetamides has been developed from readily available β-oxo amides. Upon treatment with N-halosuccinimides in water at room temperature, α,α-dihalo-β- oxo amides were produced, whereas dihaloacetamides were synthesized by treatment of β-oxo amides with N-halosuccinimides in ethanol under reflux. Copyright
- Wang, Jia,Li, Hongtao,Zhang, Dingyuan,Huang, Peng,Wang, Zikun,Zhang, Rui,Liang, Yongjiu,Dong, Dewen
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p. 5376 - 5380
(2013/09/02)
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- Unexpected formation of new bicyclic γ-lactams by dimerization of α-chloroacetoacetanilides
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Novel and unusual dimerization reaction of α-chloroacetoacetanilide under basic reaction condition to give structurally unique 6-oxa-3-azabicyclo[3.1.0]hexane was described.
- Han, Minsoo,Nam, Kee-Dal,Hahn, Hoh-Gyu,Shin, Dongyun
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p. 5217 - 5219
(2008/12/20)
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- Synthesis and structural assignment of oxanilo-N-arylhydrazonoyl chlorides
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Oxanilo-N-arylhydrazonoyl chlorides have been prepared from appropriate N-aryl-2-chloro-3-oxobutanamides by the Japp-Klingemann reaction. The structures of the title compounds have been established in the solid state by single-crystal X-ray structure determination and IR spectroscopy, and in solution by IR, UV, and 1H and 13C NMR spectroscopy. The results indicate that the hydrazonoyl chloride moiety adopts the (Z)-configured form. In the crystal, intramolecular hydrogen bonds generally exist between the chloride function and the hydrazone hydrogen atom, and also between the amide hydrogen atom and the double-bonded nitrogen atom of the hydrazone moiety. In solution, this intramolecular hydrogen bonding could not be detected. In compounds with an ortho-chloro-substituted NH-aryl moiety, however, the chlorine atom is involved in hydrogen bonding to the NH hydrogen atom both in the crystal and in solution. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
- Frohberg, Petra,Drutkowski, Guntram,Wagner, Christoph
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p. 1654 - 1663
(2007/10/03)
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- Synthesis of New Dihydrooxathiino[2,3-b]quinoline
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A synthesis of new dihydrooxathiinoquinoline 4 is described. The key compound 6 was prepared by known methods from acetoacetanilide 1. A condensation of β-chlorosulfide 6 in 75% aqueous sulfuric acid gave quinolone 5. Conversion of 5 to 4 was achieved by treatment with potassium hydroxide in ethanol solution.
- Hahn, Hoh-Gyu,Chang, Kee Hyuk,Lee, Wha Suk,Yoo, Ji Uk
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p. 2055 - 2057
(2007/10/03)
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- Process for the produciton of 2-chloroacetoacetic acid amides
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Process for the production of 2-chloroacetoacetic acid amides. Diketene is converted at a temperature of +30° to -40° C. with the help of hydrogen chloride into acetoacetic acid chloride. Chlorine is introduced into the mixture at a temperature of +30° to -40° C., whereby 2-chloroacetoacetic acid chloride is formed. The latter is converted into the corresponding amide at a temperature of +50° to -40° C. by reaction with a N-compound having the formula: STR1 wherein (i) R=R'=H, or (ii) R=R'=alkyl, substituted alkyl, aryl, substituted aryl, alkyl aryl, substituted alkyl aryl, alkoxy aryl, substituted alkoxy aryl, alkoxy alkyl or substituted alkoxy alky, or (iii) R=H, and R'=alkyl, substituted alkyl, aryl, substituted aryl, alkyl aryl, substituted alkyl aryl, alkoxy aryl, substituted alkoxy aryl, alkoxy alkyl or substituted alkoxy alkyl.
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- Preparation and Antiinflammatory Activity of 2- and 4-Pyridones
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Several N-alkyl- and N-arylacetoamides have been self-condensed to form pyridones.N-Alkylacetoacetamides give 2-pyridones, while N-arylacetoamides give 4-pyridones.In an attempt to develop nonacidic, nonsteroidal antiinflammatory agents, the pyridones were tested in a carrageenan-induced pedal edema assay in rats.While the 2-pyridones were not active, 9 of 17 4-pyridones tested were active, and one compound (4g) had antiinflammatory efficacy in a dose-response assay (ED50 values).Most compounds were considered nontoxic by determination of approximate LD50 values in mice by a standard multidimensional observational assay.
- Pierce, James Benjamin,Ariyan, Zaven S.,Ovenden, Gaye Stuart
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p. 131 - 136
(2007/10/02)
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