Tetrahedron p. 3745 - 3764 (1998)
Update date:2022-08-03
Topics:
Bast, Klaus
Durst, Toni
Huisgen, Rolf
Lindner, Klaus
Temme, Robert
The cycloadducts of isoquinoline N-phenylimide and ethylenic dipolarophiles are a new class of ene-phenylhydrazines. Their hydrazo rearrangement corresponds to the key step of Fischer's indole synthesis, but the reaction stops at the 2-aminoindoline stage, e.g., 16, because too much strain would build up in the 8-membered ring on indole formation. The model 23, lacking the medium-sized ring, smoothly undergoes indolization. The structures of type 16a aminals - besides the all-H parent mainly the diastereoisomeric 12,13-dicarboxylic esters and 13-carbonitriles - were clarified by X-ray and NMR analyses as well as by conversions. The pentacyclic aminals form a rigid bowl; the boat vs. chair conformation of the hydropyrimidine ring C is discussed.
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