Efficient syntheses of polyannular heterocycles featuring microwave-accelerated Bischler-Napieralski reaction, stereoselective Heck cyclization, and Claisen rearrangement

Citation
F. Sanchez-sancho et al., Efficient syntheses of polyannular heterocycles featuring microwave-accelerated Bischler-Napieralski reaction, stereoselective Heck cyclization, and Claisen rearrangement, SYNLETT, (4), 2000, pp. 509-513
Citations number
28
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
4
Year of publication
2000
Pages
509 - 513
Database
ISI
SICI code
0936-5214(200004):4<509:ESOPHF>2.0.ZU;2-Z
Abstract
We report the synthesis of the polyannular heterocyclic compounds 1-7. The polyannular systems in the target molecules have been obtained using stereo selective Heck reactions of suitable o-substituted iodoarenes. Additionally , the first report on microwave-accelerated Bischler-Napieralski reaction i s disclosed, which has been used in the syntheses of heterocycles 1-3. The compound 7, bearing a quaternary stereogenic center, has been prepared thro ugh a stereo-controlled Claisen-Johnson rearrangement from a derivative of the allylic alcohol 25.