Bulletin of the Chemical Society of Japan p. 853 - 859 (1989)
Update date:2022-09-26
Topics: one-pot synthesis 2-oxazolidinones
Shibata, Ikuya
Nakamura, Kenji
Baba, Akio
Matsuda, Haruo
Novel types of compounds, N-tributylstannyl-2-oxazolidinone (4a) and tetrahydro-2H-1,3-oxazin-2-one (4b), are formed from the adduct of (n-Bu3Sn)2O (1) with ω-haloalkyl isocyanate (2), and the subsequent coupling reaction with alkyl halides gives a variety of N-substituted 2-oxazolidinones and tetrahydro-2-oxazinones in a one-pot procedure.Both the cyclization and the coupling reaction proceed quantitatively in the presence of HMPA which enhances the reactivity of the Sn-heteroatom bond by coordination.
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Doi:10.1055/s-1999-3641
(1999)Doi:10.1016/0040-4039(71)80003-5
(1971)Doi:10.1039/a808894b
(1999)Doi:10.1021/ol9903741
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(1982)
