The Synthesis of Multifunctionalized 1,3-Oxazin-4-ones from Donor–Acceptor Cyclopropanes

The Synthesis of Multifunctionalized 1,3-Oxazin-4-ones from Donor–Acceptor Cyclopropanes

A series of electronically diverse imines were found to readily react with various donor–acceptor cyclopropyl acid chlorides, with complete regioselectivity, to form 1,3-oxazin-4-ones in moderate yields (25–48% over two steps). Select oxazinones underwent a base induced rearrangement to afford the c...

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Veröffentlicht in:Journal of organic chemistry 2016-03, Vol.81 (5), p.2099-2105
Hauptverfasser: Smith, Robert J, Mills, Daniel A, Nhu, Duong, Tan, Eng Wui, Lucas, Nigel T, Hawkins, Bill C
Format: Artikel
Sprache:eng
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Zusammenfassung:A series of electronically diverse imines were found to readily react with various donor–acceptor cyclopropyl acid chlorides, with complete regioselectivity, to form 1,3-oxazin-4-ones in moderate yields (25–48% over two steps). Select oxazinones underwent a base induced rearrangement to afford the corresponding cycloheptene-fused oxazinones in good yields (up to 70%).
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00112