• Title/Summary/Keyword: Regiochemistry

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Mechanistic Studies for the Cyclization of t-Amine Substituted Anilines and Their Utilization to the Synthesis of Pyrrolo[1,2-a]benzimidazoquinone Derivatives (4차 아민이 치환된 아닐린의 고리화반응 메카니즘 및 Pyrrolo[1,2-a]benzimidazoquinone 유도체의 합성에의 응용)

  • Lee, Chang-Hee;Baik, Ho-Jin;Kim, Kuk-Jin;Cho, Kiu-Uk;Oh, Kyung Taek
    • Journal of the Korean Chemical Society
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    • v.39 no.5
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    • pp.408-413
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    • 1995
  • A few t-amine substituted anilines and amides were synthesized and cyclized to pyrrolo[1,2-a]benzimidazole by heating in various solvents having different polarity. Subsequent nitration of cyclized compound followed by reduction and oxidation of resulting amine afforded quinone such as 7 in 14% yield. The formation of imidazole moiety by thermal cyclization was independent on the solvent polarity. The regiochemistry for the nitration of 4 was unambiguously determined by chemical transformation.

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Oxidative Potential of Some Endophytic Fungi Using 1-Indanone as Substrate

  • Fill, Taicia Pacheco;Silva, Jose Vinicius Da;Oliveira, Kleber Thiago De;Silva, Bianca Ferreira Da;Rodrigues-Fo, Edson
    • Journal of Microbiology and Biotechnology
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    • v.22 no.6
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    • pp.832-837
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    • 2012
  • The oxidative potential of the fungus Penicillium brasilianum, a strain isolated as endophytic from a Meliaceae plant (Melia azedarach), was investigated using 1-indanone as substrate to track the production of monooxygenases. The fungus produced the dihydrocoumarin from 1-indanone with the classical Baeyer-Villiger reaction regiochemistry, and (-)-(R)-3-hydroxy-1-indanone with 78% ee. Minor compounds that had resulted from lipase and SAM activities were also detected. The biotransformation procedures were also applied using a collection of Penicillium and Aspergillus fungi obtained from M. azedarach and Murraya paniculata. The results showed that Baeyer-Villiger were mostly active in fungi isolated from M. azedarach. Almost all fungi tested produced 3-hydroxy-1-indanone.

Partial Synthesis of Fibrostatins (Fibrostatins의 부분 합성)

  • Kwan Hee Lee;Harold w. Moore
    • Journal of the Korean Chemical Society
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    • v.47 no.1
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    • pp.47-58
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    • 2003
  • Fibrosstatins, which were isolated from the culture broth of Streptomyces catanulae subsp. griseospora, are naphthoquinones which can work as alkylating agents. It is important to synthesize these quinone compounds for the study of their biological activities. In this paper, an efficient method, Hooker oxidation, to control the regiochemistry in the synthesis of fibrostatin B is reported.

meso-Substituted Dipyrromethanes from Vinylogous Aromatic Heterocycles and Their Utilization to the Synthesis of meso-Functionalized Porphyrins

  • Hong, Seong-Jin;Lee, Mi-Hye;Lee, Chang-Hee
    • Bulletin of the Korean Chemical Society
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    • v.25 no.10
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    • pp.1545-1550
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    • 2004
  • meso-Functionalized dipyrromethanes 6-10 were synthesized by acid-catalyzed addition of pyrrole to ${\alpha}$-position of 2-alkenyl pyrroles. The regiochemistry of the reaction can be explained by either the formation of more stable carbocation intermediate or ${\beta}$-addition of ${\alpha},{\beta}$-unsaturated carbonyl compounds. The starting 2-alkenyl pyrroles were synthesized by Aldol condensation of 2-formylpyrrole with active methylene compounds such as nitromethane, diethylmalonate and malononitrile. Attempted ‘2+2' condensation of meso-diethylmalonyldipyrromethane, meso-(p-tolyl)dipyrromethane and p-tolualdehyde afforded three different porphyrins 12, 13 and 14 in reasonable yields. On the other hand, meso-(nitromethyl)dipyrromethane with p-(tbutyl) benzaldehyde resulted in the formation of three different porphyrins such as 5,15-dicyano-10,20-diarylporphyrin (16), 5-cyano-15-formyl-10,20-diarylporphyrin (17) and 5,15-diformyl-10,20-diarylporphyrin (18) in low yields. Conversion of nitromethyl groups to nitrile and (or) formyl group was observed under the porphyrin forming conditions.