ArticleTetrahedron2016
Intramolecular (4 + 2) cycloaddition of aryl-1-aza-2-azoniaallene salts: A practical approach to highly sterically-congested polycyclic protonated azomethine imines.
Article in Tetrahedron, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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2 authors at 1 institution in 1 country.
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Abstract
We report an improved two-step reaction sequence that gives tricyclic protonated azomethine imine products containing a 1,2,3,4-tetrahydrocinnoline scaffold in high yield. This sequence involves the oxidation of aryl hydrazones with TFAA-activated DMSO to give the corresponding α-trifluoroacetoxyazo products, which react readily with TMSOTf to give 1-aza-2-azoniaallene salt intermediates that undergo intramolecular (4+2) cycloadditions with pendent alkenes. This reaction sequence is more general, more practical and more environmentally friendly than our initially reported method. The cycloaddition provides exceptionally sterically-hindered products in high yield.
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