Download PDF
Synlett 2000; 2000(4): 509-513
DOI: 10.1055/s-2000-6571
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Efficient Syntheses of Polyannular Heterocycles Featuring Microwave-Accelerated Bischler-Napieralski Reaction, Stereoselective Heck Cyclization, and Claisen Rearrangement

Francisco Sánchez-Sancho* , Enrique Mann, Bernardo Herradón
  • *Instituto de Química Orgánica General, C.S.I.C., Juan de la Cierva 3, 28006 Madrid, Spain; Fax +34-91-5 64 48 53; E-mail: herradon@iqog.csic.es
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

We report the synthesis of the polyannular heterocyclic compounds 1-7. The polyannular systems in the target molecules have been obtained using stereoselective Heck reactions of suitable o-substituted iodoarenes. Additionally, the first report on microwave-accelerated Bischler-Napieralski reaction is disclosed, which has been used in the syntheses of heterocycles 1-3. The compound 7, bearing a quaternary stereogenic center, has been prepared through a stereo-controlled Claisen-Johnson rearrangement from a derivative of the allylic alcohol 25.

polyannular heterocyclic compounds - Bischler-Napieralski reaction - Heck reaction - Claisen rearrangement - Lawesson reaction