Unexpected reactivity of pyridinium salts toward alkynyl Fischer complexes to produce oxo‐heterocycles |
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| Authors: | María Inés Flores‐Conde Fabiola N de la Cruz Julio López J Óscar C Jiménez‐Halla Eduardo Peña‐Cabrera Marcos Flores‐Álamo Francisco Delgado Miguel A Vázquez |
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| Affiliation: | 1. Departamento de Química, Universidad de Guanajuato, Guanajuato, Gto, México;2. Facultad de Ciencias Químicas, Universidad Autónoma de Coahuila, Saltillo, Coah, México;3. Facultad de Química, Universidad Nacional Autónoma de México, CDMX, México;4. Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas‐IPN, CDMX, México |
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| Abstract: | The unprecedented reaction of ketone‐containing aromatic pyridinium salts 3a ‐ e and alkynyl Fischer complexes 1a ‐ f proceeds via a mild domino process to provide 4,6‐disubstituted pyran‐2‐ones 5a ‐ k and 2,3,5‐trisubstituted furans 6a ‐ h (45‐97%). According of the results of isotopic labeling experiments, a mechanism involving an initial Michael addition appears to be the key step, obtaining a mesomeric structure responsible for the formation of both products. |
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| Keywords: | Alkynyl Fischer carbene disubstituted 2H‐pyran‐2‐one pyridine ylide trisubstituted furan |
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