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Single‐Step Modular Synthesis of Unsaturated Morpholine N ‐Oxides and Their Cycloaddition Reactions
Author(s) -
Son Jongwoo,
Kim Ki Hwan,
Mo DongLiang,
Wink Donald J.,
Anderson Laura L.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201611791
Subject(s) - morpholine , cycloaddition , chemistry , reactivity (psychology) , combinatorial chemistry , surface modification , organic chemistry , catalysis , medicine , alternative medicine , pathology
Abstract A single‐flask procedure for the generation of α‐keto‐ N ‐alkenylnitrones through a Chan–Lam coupling and subsequent spontaneous 6π electrocyclization of these intermediates for the synthesis of 2 H ‐1,4‐oxazine N ‐oxides has been developed for a variety of α‐ketooximes and alkenylboronic acids. This transformation provides a new approach to C‐substituted unsaturated morpholine derivatives that are poised to undergo further functionalization for the preparation of a diverse array of novel heterocyclic structures. The scope of the new method for the synthesis of 2 H ‐1,4‐oxazine N ‐oxides is discussed, in addition to initial studies describing the cycloaddition reactivity of these new heterocyclic intermediates.