Cobalt‐Mediated [2+2+2] Cycloaddition versus CH and NH Activation of Pyridones and Pyrazinones with Alkynes: An Experimental Study | Zendy

Aubert Corinne | Zendy; Betschmann Patrick | Zendy; Eichberg Michael J. | Zendy; Gandon Vincent | Zendy; Heckrodt Thilo J. | Zendy; Lehmann Jürg | Zendy; Malacria Max | Zendy; Masjost Birgit | Zendy; Paredes Elisa | Zendy; Vollhardt K. Peter C. | Zendy; Whitener Glenn D. | Zendy

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Cobalt‐Mediated [2+2+2] Cycloaddition versus CH and NH Activation of Pyridones and Pyrazinones with Alkynes: An Experimental Study

Author(s) -

Aubert Corinne,

Betschmann Patrick,

Eichberg Michael J.,

Gandon Vincent,

Heckrodt Thilo J.,

Lehmann Jürg,

Malacria Max,

Masjost Birgit,

Paredes Elisa,

Vollhardt K. Peter C.,

Whitener Glenn D.

Publication year - 2007

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.200601823

Subject(s) - cycloaddition , reactivity (psychology) , chemistry , cobalt , medicinal chemistry , stereochemistry , catalysis , combinatorial chemistry , organic chemistry , medicine , alternative medicine , pathology

The reactivity of a range of pyridone and pyrazinone derivatives towards alkynes in the presence of cyclopentadienylcobaltbis(ethene) has been investigated. Depending on the nature of the substrates, [2+2+2]‐ or [2+2] cycloaddition, CH, or NH activation may occur. In the case of pyridones, the first three predominated with N‐protected derivatives, whereas substrates containing NH bonds followed an NH activation pathway. The [2+2+2] cycloaddition of an N ‐butynylisoquinolone was applied successfully to the total synthesis of anhydrolycorinone. Pyrazinone substrates showed similar patterns of reactivity.

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