Chemoselective Carbenoid Reactions of Furan/Thiophene/Pyrrole Ring Containing Carbonyl and Conjugated Carbonyl at Their 2-Positions

Seyma Gungor F. Ş. , Merey G., Anaç O.

ChemistrySelect, vol.5, no.17, pp.5337-5340, 2020 (Journal Indexed in SCI Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 5 Issue: 17
  • Publication Date: 2020
  • Doi Number: 10.1002/slct.202000584
  • Title of Journal : ChemistrySelect
  • Page Numbers: pp.5337-5340


© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimSeveral 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.