Article

 

Synthesis of α-Ketoester- and α-Hydroxyester-Substituted Isoindazoles via the Thermodynamic Coarctate Cyclization of Ester-Terminated Azo-Ene-Yne Systems Public Deposited

Downloadable Content

Download PDF
https://ir.library.oregonstate.edu/concern/articles/tt44pr97j

Descriptions

Attribute NameValues
Creator
Abstract
  • The synthesis of isoindazoles bearing α-ketoester and α-hydroxyester groups via the coarctate cyclization of ester terminated azo-ene-yne precursors is described. Whereas previous studies on isoindazole formation have shown the reaction to proceed through a kinetic coarctate pathway, functionalization of the terminal acetylene with a methyl ester sufficiently stabilizes the carbene intermediate to make the coarctate cyclization the thermodynamic pathway. Density functional theory (DFT) computations reveal ca. 8-9 kcal mol⁻¹ lower energy transition states for the coarctate pathway compared to the parent system.
Resource Type
DOI
Date Available
Date Issued
Citation
  • McClintock, S. P., Forster, N., Herges, R., & Haley, M. M. (2009). Synthesis of α-Ketoester-and α-Hydroxyester-Substituted Isoindazoles via the Thermodynamic Coarctate Cyclization of Ester-Terminated Azo-Ene-Yne Systems. Journal of Organic Chemistry, 74(17), 6631-6636. doi:10.1021/jo9011283
Journal Title
Journal Volume
  • 74
Journal Issue/Number
  • 17
Academic Affiliation
Rights Statement
Related Items
Funding Statement (additional comments about funding)
  • We thank the National Science Foundation (CHE-0718242) for support of this research. S.P.M. acknowledges the NSF for an IGERT fellowship (DGE-0549503). N.F. acknowledges the NSF for a summer undergraduate STEP (UCORE) fellowship (DUE-0622620). This publication was made possible, in part, by the Mass Spectrometry Facilities and Services Core of the Environmental Health Sciences Center, Oregon State University, grant number P30 ES00210, National Institute of Environmental Health Sciences, National Institutes of Health.
Publisher
Peer Reviewed
Language
Replaces
Additional Information
  • This is an author's peer-reviewed final manuscript, as accepted by the publisher.
  • description.provenance : Made available in DSpace on 2014-11-18T18:06:59Z (GMT). No. of bitstreams: 1HaleyMichaelChemistryBiochemistrySynthesisKetoester.pdf: 241131 bytes, checksum: cfe91d4161326deef77341c28d12150a (MD5) Previous issue date: 2009-07-30
  • description.provenance : Approved for entry into archive by Erin Clark(erin.clark@oregonstate.edu) on 2014-11-18T18:06:59Z (GMT) No. of bitstreams: 1HaleyMichaelChemistryBiochemistrySynthesisKetoester.pdf: 241131 bytes, checksum: cfe91d4161326deef77341c28d12150a (MD5)
  • description.provenance : Submitted by Erin Clark (erin.clark@oregonstate.edu) on 2014-11-18T18:06:47ZNo. of bitstreams: 1HaleyMichaelChemistryBiochemistrySynthesisKetoester.pdf: 241131 bytes, checksum: cfe91d4161326deef77341c28d12150a (MD5)

Relationships

Parents:

This work has no parents.

Items