Synthesis of 2,6-diary1-1,2-dihydropyridines through a 6 pi-electrocyclization of N-sulfonylazatrienesle
authors Resende, DISP; Guieu, S; Oliva, CG; Silva, AMS
nationality International
journal TETRAHEDRON LETTERS
author keywords 12-Dihydropyridines; 6 pi-Aza-electrocyclization; N-Sulfonylazatrienes; (E,E)-cinnamylideneacetophenones; MW-irradiation
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
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.
publisher PERGAMON-ELSEVIER SCIENCE LTD
issn 0040-4039
year published 2014
volume 55
issue 48
beginning page 6585
ending page 6588
digital object identifier (doi) 10.1016/j.tetlet.2014.10.034
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000345488900018
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journal impact factor 2.125
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