Sequential Diels-Alder reaction of in situ generated 2,3-dimethylenepyrrole and carbodienophiles: Rapid synthesis of 2,3,6,7-tetrasubstituted carbazoles

Authors
Vessels, JT Janicki, SZ Petillo, PA
Citation
Jt. Vessels et al., Sequential Diels-Alder reaction of in situ generated 2,3-dimethylenepyrrole and carbodienophiles: Rapid synthesis of 2,3,6,7-tetrasubstituted carbazoles, ORG LETT, 2(1), 2000, pp. 73-76
Citations number
36
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
1
Year of publication
2000
Pages
73 - 76
Database
ISI
SICI code
1523-7060(200001)2:1<73:SDROIS>2.0.ZU;2-M
Abstract
[GRAPHICS] 2,3,6,7-Tetrasubstituted-1,2,3,4,5,6,7,8-octahydrocarbazoles 2 were synthes ized in 46-90% yields by sequential Diels-Alder reactions from N-benzyl-2,5 -dimethyl-3,4-bisacetoxymethylpyrrole (1) and dienophiles such as maleic an hydride, maleimides, ethyl maleate, fumaronitrile, and ethyl acrylate. The 2,3,6,7-tetrasubstituted carbazoles 3 were then synthesized in 32-87% yield s from 2 by oxidation with DDQ.