Synthesis of 2,6-diary1-1,2-dihydropyridines through a 6 pi-electrocyclization of N-sulfonylazatrienesle

abstract

The development of an efficient synthetic method toward substituted 1,2-dihydropyridines from cinnamylideneacetophenones is reported. The key intermediates N-sulfonylazatrienes were synthesized through a TiCI4-mediated direct condensation of primary sulfonamides with the substituted (E,E)-cinnamylideneacetophenones. The 6 pi-electrocyclization of these intermediates, catalyzed by a Lewis acid, selectively afforded the desired products in good yields. (C) 2014 Elsevier Ltd. All rights reserved.

keywords

DIELS-ALDER REACTION; STEREOSELECTIVE ASYMMETRIC 6-PI-AZAELECTROCYCLIZATION; IBOGA ALKALOID ANALOGS; FORMAL SYNTHESIS; CHIRAL ISOQUINUCLIDINES; CONJUGATE ADDITION; 1,2-DIHYDROPYRIDINES; DIHYDROPYRIDINES; (E,E)-CINNAMYLIDENEACETOPHENONES; CHEMISTRY

subject category

Chemistry

authors

Resende, DISP; Guieu, S; Oliva, CG; Silva, AMS

our authors

acknowledgements

Thanks are due to the University of Aveiro and the Portuguese Fundacao para a Ciencia e a Tecnologia (FCT) for funding the Organic Chemistry Research Unit (project PEst-C/QUI/UI0062/ 2013), the CICECO Associate Laboratory (PEst-C/CTM/LA0011/2013), and the Portuguese National NMR Network (RNRMN). D.I.S.P.R. and S.G. also thank the FCT for a doctoral grant (SFRH/BD/62696/2009) and a postdoctoral grant (SFRH/BPD/70702/2010), respectively.

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