Synthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C-H Activation

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A convenient one-pot C-H alkenylation/electrocyclization/aromatization sequence has been developed for the synthesis of highly substituted pyridine derivatives from alkynes and {alpha},{beta}-unsaturated N-benzyl aldimines and ketimines that proceeds through dihydropyridine intermediates. A new class of ligands for C-H activation was developed, providing broader scope for the alkenylation step than could be achieved with previously reported ligands. Substantial information was obtained about the mechanism of the reaction. This included the isolation of a C-H activated complex and its structure determination by X-ray analysis; in addition, kinetic simulations using the Copasi software were employed to determine rate constants for this transformation, implicating facile ... continued below

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Ellman, Jonathan A.; Colby, Denise & Bergman, Robert November 20, 2007.

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A convenient one-pot C-H alkenylation/electrocyclization/aromatization sequence has been developed for the synthesis of highly substituted pyridine derivatives from alkynes and {alpha},{beta}-unsaturated N-benzyl aldimines and ketimines that proceeds through dihydropyridine intermediates. A new class of ligands for C-H activation was developed, providing broader scope for the alkenylation step than could be achieved with previously reported ligands. Substantial information was obtained about the mechanism of the reaction. This included the isolation of a C-H activated complex and its structure determination by X-ray analysis; in addition, kinetic simulations using the Copasi software were employed to determine rate constants for this transformation, implicating facile C-H oxidative addition and slow reductive elimination steps.

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  • Journal Name: Journal of the American Chemical Society

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  • Report No.: LBNL-1479E
  • Grant Number: DE-AC02-05CH11231
  • Office of Scientific & Technical Information Report Number: 948125
  • Archival Resource Key: ark:/67531/metadc894846

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Office of Scientific & Technical Information Technical Reports

Reports, articles and other documents harvested from the Office of Scientific and Technical Information.

Office of Scientific and Technical Information (OSTI) is the Department of Energy (DOE) office that collects, preserves, and disseminates DOE-sponsored research and development (R&D) results that are the outcomes of R&D projects or other funded activities at DOE labs and facilities nationwide and grantees at universities and other institutions.

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  • November 20, 2007

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  • Sept. 27, 2016, 1:39 a.m.

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  • Sept. 30, 2016, 7:13 p.m.

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Ellman, Jonathan A.; Colby, Denise & Bergman, Robert. Synthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C-H Activation, article, November 20, 2007; Berkeley, California. (digital.library.unt.edu/ark:/67531/metadc894846/: accessed November 17, 2017), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT Libraries Government Documents Department.