Synthesis and [3+2] cycloaddition reaction of 3-[(trimethylsilylmethylamino)(methylthio)methylene]heterocyclic compounds

Citation
Y. Tominaga et al., Synthesis and [3+2] cycloaddition reaction of 3-[(trimethylsilylmethylamino)(methylthio)methylene]heterocyclic compounds, J HETERO CH, 38(5), 2001, pp. 1143-1151
Citations number
16
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022-152X → ACNP
Volume
38
Issue
5
Year of publication
2001
Pages
1143 - 1151
Database
ISI
SICI code
0022-152X(200109/10)38:5<1143:SA[CRO>2.0.ZU;2-G
Abstract
3-[(Trimethylsilylmethylamino)(methylthio)]methylene-2-coumaranone (4a) and 1-methyloxindole (4b), readily prepared by reactions of the corresponding bis(methylthio)methylene heterocyclic compounds (2a,b), with (trimethylsily lmethyl)amine (3), were found to be synthetic equivalents of heterocyclic a lkylidene-azomethine ylides. Reactions of 4a, b with reactive heterodipolar ophiles such as aldehydes and ketones and reactive alkenes in the presence of cesium fluoride gave the 1,3-dipolar cycloadducts, 3-(2-oxazolidinyliden e)-oxindole and -coumaran-2-one derivatives (8a-j, 9a-b), as well as pyrrol ylidenecoumaran-2-one and oxindole derivatives (12-15, 17, 18), via the 1,3 -elimination of (methylthio)trimethylsilane.