Intramolecular azavinyl carbene-triggered rearrangement of furans

• Verfasst von: Makarov, Anton S. [VerfasserIn]
• Verfasst von: Uchuskin, Maxim G. [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Intramolecular azavinyl carbene-triggered rearrangement of furans
• Verf.angabe: Anton S. Makarov, Maxim G. Uchuskin, A. Stephen K. Hashmi
• E-Jahr: 2019
• Jahr: 26 July 2019
• Umfang: 6 S.
• Fussnoten: Gesehen am 31.10.2019
• Titel Quelle: Enthalten in: Chemical science
• Ort Quelle: Cambridge : RSC, 2010
• Jahr Quelle: 2019
• Band/Heft Quelle: 10(2019), 37, Seite 8583-8588
• ISSN Quelle: 2041-6539
• DOI: doi:10.1039/C9SC02299F
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1680813692

Abstract

An intramolecular rhodium-catalyzed reaction of 1-tosyl-1,2,3-triazoles with furans has been explored. The tosylimino functionality was found to play a significant chemical role participating in the subsequent domino-transformations of a key reaction intermediate. One of the reaction pathways leads to valuable 2-formyl- and 2-acetylpyridine building blocks, which could be obtained in one-pot starting from easily accessible (furan-2-ylmethyl)propargyl amines. An original method for the synthesis of highly functionalized indolizines from the obtained pyridines has been proposed.