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    Öğe
    Chemoselective Carbenoid Reactions of Furan/Thiophene/Pyrrole Ring Containing Carbonyl and Conjugated Carbonyl at Their 2-Positions
    (Wiley-V C H Verlag Gmbh, 2020) Seyma Gungor, Fusun; Merey, Gokce; Anac, Olcay
    Several furyl/thiophenyl/N-methylpyrrolyl cores having aldehyde/ketone/ene-biscarbonyl/diene-biscarbonyl functions at their 2-positions were reacted with diazocarbonyl compounds in the presence of metal catalysts. Between the two possible reaction pathways which may take place either on the 2-substituent of hetaryl or on the core structure, only one of them was dominant for each reaction depending on substituents. Accordingly, in the reaction of thiophene-2-carbaldehyde with diazo compounds we obtained epoxy derivatives. On the other hand, dimethyl diazomalonate and furyl-ene-diketo/N-methylpyrrolyl-ene-diester yielded only novel dihydrofuran derivatives via [1,5]-electrocyclic ring closure. However, the reactions of 2-ene/diene-diester functionalized furans with dimethyl diazomalonate resulted polymethoxycarboxylate-substituted oxo-polyenes chemo-specifically in good yields.
  • [ X ]
    Öğe
    CuCl/AgSbF6 and Rh-2(OAc)(4) Comparison for the Synthesis of N-O Tethered Three and Five Membered Rings via Diazo Chemistry
    (Chemical Soc Japan, 2021) Merey, Gokce; Kubilay, H. Nur; Anac, Olcay
    Diazocarbonyl compounds are versatile precursors of carbenes leading to various structures by using several metal catalysts, especially copper and rhodium salts. In this study, eight different diazocarbonyls having N-O moiety were used. The N-O tethered structures were prefened because they may allow some useful transformations of the final products into valuable compounds via N-O cleavage. In the presence of a double bond on the -OR function of the starting diazo compound, CuCl/AgSbF6 catalyst yielded only cyclopropyl fused oxazinane/oxazepane derivatives over cyclopropanation while Rh-2(OAc)(4) catalyst was giving mainly isooxazolidinones via C-H insertion.