Fused heterocycles with nitrogen incorporation are of
particular
bioactive use and high importance in many research fields, especially
isoquinoline-based [6/6/5] tricycles. Here, we report a unique strategy
to access multifunctional N-fused tricycles from α,β-unsaturated
isoquinoline ketone and sulfonamide under mild reaction conditions.
The methodology features wide substrate tolerance, and a set of N-fused
heteroarenes including quinoline, phthalazine, quinazoline, quinoxaline,
and benzothiazole cores are furnished efficiently. Moreover, the protocol
is easy to scale up to synthesize lamellarin analogues, and the amide
group of the product is also easy to transfer to other functional
groups.
The first synthesis of well-defined poly[(phenylmethylene-co-methylpropenylene)-b-methylene,[ (C1-co-C3)b-C1],t erpolymers was achieved by one-pot borane-initiated random copolymerization of w-methylallyl (C3 units,c hain is growing by three carbon atoms at at ime) and benzyltriphenylarsonium (C1 units,chain is growing by one carbon atom at at ime) ylides,f ollowed by polymerization of sulfoxonium methylide (C1 units). Other substituted arsonium ylides,s uch as prenyltriphenyl, propyltriphenyl and (4-fluorobenzyl)triphenyl can also be used instead of benzyltriphenylarsonium. The obtained terpolymers are well-defined, possess ap redictable molecular weight and low polydispersity (M n,NMR = 1.83-9.68 10 3 gmol À1 , = 1. 09-1.22). An unexpected light emission phenomenon was discoveredi nt hese non-conjugated terpolymers,asconfirmed by fluorescence and NMR spectroscopy. This phenomenon can be explained by the isomerization of the double bonds of allylic monomeric units along the chain of the terpolymers (isomerization-induced light emission).
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