Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 16, Pages 6143-6150Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo9008904
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Funding
- Russian Academy of Sciences [93]
- Chemical Service Centre of SB RAS
- National Science Foundation [CHE-0316598]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0848686] Funding Source: National Science Foundation
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This work analyzes multiple new reaction pathways which originate from intramolecular reactions of activated alkynes with the appropriately positioned multifunctional hemiaminal moiety. Combination of experimental substituent effects with Natural Bond Orbital (NBO) analysis revealed that alkyne polarization controls partitioning between these cascades. A particularly remarkable transformation leads to the formation of six new bonds at the two alkyne carbons due to complete disassembly of the alkyne moiety and formal insertion of a nitrogen atom between the two acetylenic carbons of the reactant. This reaction offers a new synthetic approach for the preparation of polycyclic aromatic amides with a number of possible applications in molecular electronics. Another of the newly discovered cascades opens access to substituted analogues of Sampangine alkaloids which are known for their antifungal and antimycobacterial activity against AIDS-related opportunistic infection pathogens.
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