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Title: A Metal-Free Domino Process for Regioselective Synthesis of 1,2,4-Trisubstituted Pyrroles: Application toward the Formal Synthesis of Ningalin B
Authors: Kumar V.
Awasthi A.
Metya A.
Khan T.
Issue Date: 2019
Abstract: A new one-pot, transition-metal, acid/base-free domino process is developed for the regioselective synthesis of 1,2,4-trisubstituted pyrroles. The process involves 1,3-dipolar cycloaddition of unsymmetrical azomethine ylide resulting from the thermal C-C bond cleavage of unactivated aziridines with ?-bromo-?-nitrostyrene, followed by a cascade of elimination and aromatization reaction sequence to preferentially furnish 1,2,4-trisubstituted pyrroles instead of the expected 1,2,3-trisubstituted pyrroles, in good to excellent yields. Further, the application of the methodology for the formal synthesis of ningalin B is delineated. � 2019 American Chemical Society.
Appears in Collections:Research Publications

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