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Synlett 2000; 2000(4): 509-513
DOI: 10.1055/s-2000-6571
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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
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Publication Date:
31 December 2000 (online)

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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

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