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Derivatives of indole-3-carbaldehyde oxime have been prepared that bear a carbon-carbon double bond at C-2 and a five- or six-membered ring linking the α-carbon artom of the vinyl group and the indole nitrogen atom. Compound 9, with a five-membered ring linking the two atoms, failed to undergo a cyclisation reaction on heating. However the oximes 16 and 22, with a six-memberd ring linking the two...
The palladium(0) catalysed coupling of 2-bromocyclopentene-1-carboxaldehyde N,N-dimethylhydrazone 1 with vinylzinc halides and with 2-furyl- and 2-thienylzinc halides provides a route to the corresponding 2-vinyl- and 2-heteroaryl-cyclopentene-1-carboxaldehyde dimethylhydrazones. These cyclise thermally to 6,7-dihydro-5H-2-pyrindines (e.g., 3).
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