jo5019848_si_002.cif (46.7 kB)
Photoassisted Diversity-Oriented Synthesis: Accessing 2,6-Epoxyazocane (Oxamorphan) Cores
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posted on 2015-12-17, 05:57 authored by Olga A. Mukhina, N. N.
Bhuvan Kumar, Teresa M. Cowger, Andrei G. KutateladzeThe
modular synthesis of photoprecursors and their photoinduced cyclization
into substituted 1-benzazocanes of two distinct topologies is described.
The key step producing an extended polyheterocyclic system involves
the photogeneration of azaxylylenes and their subsequent intramolecular
cycloaddition with furan-containing pendants tethered either via the
aniline nitrogen or through the carbonyl group containing arm. The
primary photoproductssecondary or tertiary anilines which
are not acylated at the nitrogen atomundergo facile acid-catalyzed
or spontaneous ring-opening–ring-closing rearrangement to yield
fused polyheterocyclic structures possessing a 2,6-epoxyazocane (or
oxamorphan) core.
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photoprecursorphotoproductepoxyazocaneCoresThephotogenerationpolyheterocyclic structuresbenzazocaneAccessinganiline nitrogensynthesiscorepolyheterocyclic systemcarbonyl groupOxamorphanpendantphotoinduced cyclizationPhotoassistedacylatedEpoxyazocaneintramolecular cycloadditionoxamorphanrearrangementtopologieSynthesiazaxylylene
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