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Updated: Jun 22, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Enal-azomethine ylides: application in the synthesis of functionalized pyrroles
Pratap Kumar Mandal1, Sandeep Patel1, Sreenivas Katukojvala1
1Department of Chemistry, Indian Institute of Science Education and Research, Bhopal, Madhya Pradesh, 462066 India. sk@iiserb.ac.in.
Abstract:
Rhodium-catalyzed [3 + 2] annulation of diazoenals and N-alkyl imines resulted in N-alkyl-pyrrole-3-carbaldehyde derivatives. The reaction involves thermal 6π-electrocyclization and aromatization of a new class of enal-azomethine ylides (EAYs). The EAYs derived from dihydroisoquinoline and 2H-azirine gave fused-pyrrole and pyridine derivatives, respectively. The synthetic importance of pyrrole products has been demonstrated by one-step synthesis of the biologically relevant pyrrolo[3,2-c]quinoline scaffold as well as pyrrolo[2,1-a]isoquinoline which is a core structure of lamellarin alkaloids.
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