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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Stereoselective Synthesis of Diaza-Hexatrienes via [1,6]-O-to-N Group Transfer Strategy
Srashti Bhardwaj1, Sandeep Kumar1, Janakiram Vaitla1
1Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India.
Abstract:
Herein, we report a transition metal-free synthesis of Z-configured 2,3-diaza-1,3,5-hexatrienes via a base-mediated rearrangement of O-substituted salicylaldehyde N-tosylhydrazones. This unprecedented O-to-N group transfer occurs under mild conditions, exhibits a broad substrate scope, and tolerates diverse functional groups. The resulting diazatrienes serve as precursors for heterocycles and photoswitches. This rearrangement introduces a new synthetic strategy distinct from classical phenol-based rearrangements.
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