Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 20, Pages 13033-13044Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01878
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Funding
- SERB [EMR/2014/385]
- SERB-NPDF
- ACRHEM
- CSIR
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A ruthenium (Ru)-catalyzed double annulation of easily accessible N-methoxybenzamide derivatives with unactivated alkynes for the synthesis of unusual 6,6-fused pyranoisoquinolines is described. Both ortho-C-H bonds of arenes and the N- and O-moieties of N-methoxybenzamides are involved in the construction of four [(C-C)-(C-N) and (C-C)-(C-O)] bonds in one step under single catalytic conditions. The unsymmetrical annulation of N-methoxybenzamides with two distinct alkynes is also demonstrated. The oxidizable directing group N-methoxyamine (NHOMe) assists the unsymmetrical double annulations of arenes [that use both N- and O-heteroatoms] in a single operation. This synthetic method features excellent substrate scope and tolerates a wide range of functional groups. Peripheral modification of pyranoisoquinolines for the construction of complex heterocyclic compounds is also demonstrated.
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