Journal
TETRAHEDRON
Volume 71, Issue 38, Pages 6681-6688Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.07.051
Keywords
Multicomponent reaction; Spirocycle; 1,3-Oxazine; Aldimine; Quinine; Electron-deficient alkyne
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Funding
- National Natural Science Foundation of China [21172189]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
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A series of structurally diverse spirocyclic 1,3-oxazines were conveniently prepared from three-component reactions of alpha,beta-unsaturated N-arylaldimines, dialkyl acetylenedicarboxylate and quinones in dry acetonitrile without catalyst. Various quinones including p-benzoquinone, 1,4-naphthoquinone, acenaphthenequinone, and phenanthrenequinone as well as benzil were successfully used in the reaction to give the corresponding spirocyclic 1,3-oxazines in good yields. The diastereoisomers of the obtained spirocyclic 1,3-oxazines were elucidated by H-1 NMR spectra and single crystal structures. (C) 2015 Elsevier Ltd. All rights reserved.
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