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2-Etroxy-5,6-dihydro-1,3-oxazines from triethyl azomethinetricarboxylate

✍ Scribed by H.K. Hall Jr.; Diana L. Miniutti

Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 163 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)80068-x

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✦ Synopsis

Inverse demand Diels-Alder reactions of triethyl azomethinetricarboxylate with electron-rich olefins lead to 2-ethoxy-5,6-dihydro-1,3-oxazines using the C=N-C=O moiety as the diene only. The formation of 6-alkoxy-3,4-dihydropyrans from reactions of electron-rich olefins with substituted unsaturated esters was recently reported. 192 The analogous 6-alkoxy-dihydrooxadiazine compound was found in a reaction of diethyl azodicarboxylate and l,Z-dimethoxyethene. 3 The reactions are believed to proceed through a Die&-Alder reaction with inverse electron demand using a carbonyl group adjacent to the double bond as part of the diene. J.

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