• Title/Summary/Keyword: Cyclic 1,3-dicarbonyl compounds

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1,3,5-Trichloro-2,4,6-Triazinetrion: A Versatile Heterocycle for the One-Pot Synthesis of 14-Aryl- or Alkyl -14H-Dibenzo[a,j]xanthene, 1,8-Dioxooctahydroxanthene and 12-Aryl-8,9,10,12-Tetrahydrobenzo[a]xanthene-11-one Derivatives under Solvent-Free Conditions

  • Maleki, Behrooz;Gholizadeh, Mostafa;Sepehr, Zeinalabedin
    • Bulletin of the Korean Chemical Society
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    • v.32 no.5
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    • pp.1697-1702
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    • 2011
  • A facile, green, efficient and environment-friendly protocol for the synthesis of 14-aryl- or alkyl-14Hdibenzo[a,j]xanthene, 1,8-dioxooctahydroxanthene and 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one have been developed by one-pot condensation of various aldehydes with (i) ${\beta}$-naphthol (ii) cyclic 1,3-dicarbonyl compounds and (iii) ${\beta}$-naphthol and cyclic 1,3-dicarbonyl compounds, in the presence of 1,3,5-trichloro-2,4,6-triazinetrion (trichloroisocyanuric acid, TCCA) as catalyst under solvent-free conditions. The present approach offers the advantages of clean reaction, simple methodology, short reaction time, easy purification, and economic availability of the catalyst.

Studies on the Aromatic Dihydrazines (Ⅱ). Condensation Reaction Between p-Phenylenedihydrazine and Dicarbonyl Compounds (芳香族 디히드라진에 關한 硏究 (第2報). 파라페닐렌디히드라진과 디카르보닐 化合物과의 縮合反應)

  • Lee Woo Young
    • Journal of the Korean Chemical Society
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    • v.20 no.6
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    • pp.500-506
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    • 1976
  • Structures of the products obtained from the condensation reaction between p-phenylenedihydrazine(PPDH) and dicarbonyl compounds were determined, From the reaction with PPDH, acetylacetone produced a cyclic compound, 1,1'-p-phenylene-bis-3, 5-dimetylpyrazole; ethylacetoacetate also formed a cyclic compound, 1,1'-p-phenylene-bis-3-methyl-5-pyrazolone; diacetyl yielded a simple dihydrazone, diacetyl p-phenylenedihydrazone. Condensation products from the other dicarbonyl compounds being of generally unstable, the structure determination was quite difficult.

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Efficient One-Step Synthesis of 2-Arylfurans by Ceric Ammonium Nitrate (CAN)-Mediated Cycloaddition of 1,3-Dicarbonyl Compounds to Alkynes

  • 이용록;변명환;김병소
    • Bulletin of the Korean Chemical Society
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    • v.19 no.10
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    • pp.1080-1083
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    • 1998
  • An efficient method for construction of 2-arylfiirans has been developed by ceric(IV) ammonium nitratemediated oxidative cycloaddition of cyclic and acyclic 1,3-dicarbonyl compounds to several alkynes. Reactions of 1,3-cyclohexanedione, 1,3-cyclopentanedione, and 2,4-pentanedione with several alkynes furnish 2-arylfurans in 26-75% yields. Extension of this technology to more complex 4-hydroxy-2-quinolone and 3-hydroxy-lH-phenalen-l-one with phenylacetylene also affords furoquinolinone and ftirophenalenone derivative in moderate yields. Reaction of 4-hydroxycoumarins with phenylacetylene give linear and angular furocoumarin derivatives as a mixture of regioisomer in good yields. The mechanistic pathway for the formation of 2-arylfurans has been also described.