90585-30-1Relevant academic research and scientific papers
Diaryliodonium Salt-Based Synthesis of N-Alkoxyindolines and Further Insights into the Ishikawa Indole Synthesis
Ogura, Akihiro,Shibata, Kouhei,Takao, Ken-Ichi
, p. 10067 - 10087 (2021/07/26)
A diaryliodonium salt-based strategy enabled the first systematic synthesis of rarely accessible N-alkoxyindolines. Mechanistic analyses suggested that the reaction likely involves reductive elimination of iodobenzene from iodaoxazepine via a four-membered transition state, followed by Meisenheimer rearrangement. Substrates with N-carbamate protection afforded indole in a manner similar to that of the Ishikawa indole synthesis. Preinstallation of a stannyl group as an iodonium salt precursor greatly expanded the substrate scope, and further mechanistic insights are discussed.
Mercury in Organic Chemistry. 26. Synthesis of Heterocycles via Intramolecular Solvomercuration of Aryl Acetylenes
Larock, Richard C.,Harrison, L. Wayne
, p. 4218 - 4227 (2007/10/02)
A number of ortho substituted aryl acetylenes, o-CH3XC6H4YCCR (X=O, S, CO2; Y=-, CO), have been observed to undergo facile intramolecular solvomercuration with mercuric acetate in acetic acid to afford the corresponding benzofuran, benzothiophene, isocoumarin, and chromone organomercuric chlorides, after aqueous sodium chloride workup.The aryl acetylenes m-XC6H4YCH2CCR (X=H, Y=O, R=CH3; X=CH3O, Y=CH2, R=n-C3H7) undergo similar cyclizations to yield mercurated 2H-1-benzopyrans and 1,2-dihydronaphthalenes.The mercuration and subsequent carbonylation of o-R1OC6H4CCR2 1=Si(t-Bu)Me2, R2=CH3; R1=CH3, R2=o-C6H4OCH3> has provided a new approach to the coumarin and coumestan ring systems.
