22121-86-4Relevant articles and documents
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Monnin
, p. 1983,1987 (1957)
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A tandem "on-palladium" Heck-Jeffery amination route toward the synthesis of functionalized indole-2-carboxylates
McNulty, James,Keskar, Kunal
supporting information; experimental part, p. 6902 - 6908 (2012/01/02)
A direct synthesis of functionalized indole-2-carboxylates involving a PdII-catalyzed annulation of ortho-iodoanilines onto a vinyl ether is described. The reaction mechanism is shown to be distinct from a stepwise Heck, intramolecular amination pathway, likely involving a tandem "on-palladium" Heck-Jeffery amination process incorporating a novel intramolecular amination step.
Intramolecular 4+3 cycloadditions, vinylthionium ions from allylic alcohols
Harmata,Jones
, p. 783 - 786 (2007/10/03)
Aldehyde 9 can be prepared from ethyl pyruvate in several steps. Treatment of 1 with various diene-containing Grignard reagents results in the formation of the corresponding allylic alcohol in good yield. Exposure of these alcohols to triflic anhydride results in the formation of 4+3 cycloadducts in good to excellent yields. Furan and simple butadiene trap the intermediate allylic cation efficiently in the formation of 5,7-fused ring systems. A tethered thiophene undergoes only intramolecular Friedel-Crafts alkylation.