Journal
TETRAHEDRON LETTERS
Volume 52, Issue 35, Pages 4507-4511Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.06.023
Keywords
Cyclic ketene acetal; Ambident nucleophile; Regiochemistry
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Funding
- Mississippi State University
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The five-membered cyclic ketene-N,O-acetal, 2-oxazolidin-2-ylidene-1-phenylethanone 1, and its anion 2, formed on deprotonation, are ambident nucleophiles. Compound 1 was synthesized by benzoylation of 2-methyl-2-oxazoline to give a ring-opened N,C,O-trisbenzoylation product, 9, followed by KO-double debenzoylation using methanolic KOH. Compound 1 reacted with benzoyl chloride to give N,C,O-trisbenzoylated 9, and reacted with phenyl chloroformate to give the similar ring-opened carbonic acid 3[(2-chloro-ethyl)-phenoxycarbonyl-amino]-3-oxo-1-phenyl-propenyl ester phenyl ester. 13. In contrast, ambident anion 2 reacted with benzoyl chloride to give the beta,beta-bisbenzoylated cyclic ketene-N,O-acetal, 16, and reacted with phenyl chloroformate to give the novel heterocycle 3-(2-hydroxy-ethyl)-6-phenyl-[1,3]oxazine-2.4-dione, 17. (C) 2011 Elsevier Ltd. All rights reserved.
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