Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 14, Pages 8923-8932Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00810
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- Ministerio de Economia y Competitividad of Spain [CTQ2016-77270-R]
- Consejeria de Economia y Conocimiento-Junta de Andalucia [FQM-345]
- Ministerio de Educacion, Cultura y Deporte
- Junta de Andalucia -UE (Fondo Social Europeo-Iniciativa de Empleo Juvenil) [EJ3-61]
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An efficient procedure for the preparation of beta-substituted furans/pyrroles is presented. The methodology is based on the use of 7-oxa/azanorbornadienes as dipolarophiles in 1,3-dipolar cycloaddition with benzyl azide. The triazoline cycloadduct thus formed spontaneously decomposes via a retro-Diels-Alder (rDA) reaction to afford a beta-substituted furan/pyrrole derivative and a stable triazole. The scope of this tandem 1,3-dipolar cycloaddition/rDA reaction was studied with thirteen 7-heteronor-bornadienes. This study allowed a deep knowledge of the regioselectivity of the reaction, which can be tuned through the substituents of the heteronorbornadienic systems.
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