Sulfoximine-Directed Ruthenium-Catalyzed ortho-C–H Alkenylation of (Hetero)Arenes: Synthesis of EP3 Receptor Antagonist Analogue

The reusable sulfox­imine directing-group-assisted Ru­(II)-catalyzed chemo- and regio­selective ortho-C–H alkenylation of arenes and hetero­arenes with acrylates and α,β-unsaturated ketones/vinyl sulfone is shown. The N-aroyl sulfoximine undergoes annulation with diphenyl­acetylene, delivering iso­q...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-07, Vol.79 (13), p.6123-6134
Main Authors: Yadav, M. Ramu, Rit, Raja K, Shankar, Majji, Sahoo, Akhila K
Format: Article
Language:English
Subjects:
Alkylation
Catalysis
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Hydrogen Bonding
Molecular Structure
Receptors, Prostaglandin E, EP3 Subtype - antagonists & inhibitors
Receptors, Prostaglandin E, EP3 Subtype - chemistry
Ruthenium - chemistry
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Summary:The reusable sulfox­imine directing-group-assisted Ru­(II)-catalyzed chemo- and regio­selective ortho-C–H alkenylation of arenes and hetero­arenes with acrylates and α,β-unsaturated ketones/vinyl sulfone is shown. The N-aroyl sulfoximine undergoes annulation with diphenyl­acetylene, delivering iso­quinoli­nones and methyl phenyl sulfoxide. The present protocol is successfully employed for the synthesis of the EP3 receptor antagonist analogue.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5008465