76609-29-5Relevant academic research and scientific papers
Synthesis of Indoles and Pyrroles Utilizing Iridium Carbenes Generated from Sulfoxonium Ylides
Vaitla, Janakiram,Bayer, Annette,Hopmann, Kathrin H.
, p. 4277 - 4281 (2017/04/03)
Metal carbenes can undergo a myriad of synthetic transformations. Sulfur ylides are potential safe precursors of metal carbenes. Herein, we report cascade reactions that involve carbenoids derived from sulfoxonium ylides for the efficient and regioselective synthesis of indoles and pyrroles. The tandem action of iridium and Br?nsted acid catalysts enables rapid assembly of the heterocycles from unmodified anilines or readily accessible enamines under microwave irradiation. The key mechanistic steps are the catalytic transformation of the sulfoxonium ylide into an iridium–carbene complex, followed by N?H or C?H functionalization of an aniline or enamine, respectively, and a final acid-catalyzed cyclization. The present method was successfully applied to the synthesis of the densely functionalized pyrrole subunit of atorvastatin.
Exploiting the chemistry of strained rings: Synthesis of indoles via domino reaction of aryl iodides with 2 H-azirines
Candito, David A.,Lautens, Mark
supporting information; experimental part, p. 3312 - 3315 (2010/10/19)
(Equation Presented). The highly strained 2H-azirine ring system has been the source of considerable theoretical and synthetic work. The reaction of these strained heterocycles with transition metals has been documented to give rise to ring opening and subsequent formation of varied heterocycles. An interesting domino reaction is described wherein the strained bicyclic alkene, norbornene, mediates the reaction of 2H-azirines with aryl iodides under palladium catalysis to provide indole or polycyclic dihydroimidazole heterocycles.
Synthesis of Some New Fluorinated Indoles and Benzindoles through Pyridinium Ylids
Bansal, R. K.,Bhagchandani, Gope
, p. 801 - 802 (2007/10/02)
Three fluorinated phenacylpyridinium bromides (1a-c) have been prepared and reacted with various anilines to obtain 2-(fluoroaryl)indoles (3a-r).A similar reaction of 1 with 1- and 2-naphthylamines furnishes 2-(fluoroaryl)-1H-benzindoles (4a-c) and 2-(fluoroaryl)-3H-benzindoles (5a-c), respectively.All the products have been identified on the basis of elemental analyses, IR, PMR and 19F NMR spectra.
