Isoquinolinium N-arylimides and acetylenic dipolarophiles; cycloadducts and their rearrangements
…, R Huisgen, K Lindner, DS Stephenson, R Temme
Index: Bast, Klaus; Durst, Tony; Huber, Helmut; Huisgen, Rolf; Lindner, Klaus; Stephenson, David S.; Temme, Robert Tetrahedron, 1998 , vol. 54, # 29 p. 8451 - 8468
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Citation Number: 6
Abstract
Dimethyl acetylenedicarboxylate, methyl propiolate, and ethyl phenylpropiolate surpass the corresponding ethylenic carboxylic esters in dipolarophilic activity vs. isoquinolinium N- arylimides, a class of azomethine imines. The cycloadducts contain a Nß- vinylphenylhydrazine system and enter into a Fischer indole synthesis which stops one step short of the indole. The [3.3]-sigmatropic rearrangement involved is likewise faster for the ...
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