Pseudoesters and derivatives. Part 38. 1,3-dipolar cycloadditions of aryl azides and an aziridine, via azomethine ylide, to 2(5H)-furanones substituted at the 5-position by methoxy and sulfur bearing groups

Authors
Gonzalez, G Martin, MV Paredes, MC
Citation
G. Gonzalez et al., Pseudoesters and derivatives. Part 38. 1,3-dipolar cycloadditions of aryl azides and an aziridine, via azomethine ylide, to 2(5H)-furanones substituted at the 5-position by methoxy and sulfur bearing groups, HETEROCYCLE, 52(1), 2000, pp. 237-251
Citations number
38
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
52
Issue
1
Year of publication
2000
Pages
237 - 251
Database
ISI
SICI code
0385-5414(20000101)52:1<237:PADP31>2.0.ZU;2-#
Abstract
The behavior of the 2(5H)-furanones (1-3) towards p-methoxy- and p-nitrophe nyl azides (4 and 12) has been investigated, in particular with respect to the regio- and stereoselectivity. The 1,3-dipolar cycloaddition of the azom ethine ylide generated by thermal ring opening of dimethyl trans-1-(p-metho xyphenyl)aziridine-2,3-dicarboxylate (22) to 2(5H)-furanones (1-3) proceeds in good yield and affords functionalized furo[3,4-c]pyrrol-3-one derivativ es.