442155-83-1Relevant academic research and scientific papers
Divergent Pd(ii) and Au(iii) mediated nitroalkynol cycloisomerizations
Patel, Pitambar,Ramana, Chepuri V.
supporting information; experimental part, p. 7327 - 7334 (2011/11/30)
A new cycloisomerization reaction comprising the simultaneous addition of nitro and alcohol groups across CC leading to skeletally diverse small molecules is documented.
The versatile role of norbornene in C-H functionalization processes: concise synthesis of tetracyclic fused pyrroles via a threefold domino reaction
Gericke, Kersten M.,Chai, David I.,Lautens, Mark
, p. 6002 - 6014 (2008/12/20)
The synthesis of novel tetracyclic fused pyrroles from 1-(2-iodophenyl)-1H-pyrrole and various bromoalkyl-aryl alkynes via a palladium(0)-catalyzed and norbornene-mediated threefold domino reaction is reported. PdCl2 and tri-2-furylphosphine (TFP) in the presence of norbornene and Cs2CO3 in CH3CN at 90 °C gave a variety of tetracyclic fused pyrroles in usually high yields. In the described reaction sequence two of the three carbon-carbon bonds are formed by functionalization of an unactivated aryl C-H bond.
Development of an Efficient Procedure for Indole Ring Synthesis from 2-Ethynylaniline Derivatives Catalyzed by Cu(II) Salts and Its Application to Natural Product Synthesis
Hiroya, Kou,Itoh, Shin,Sakamoto, Takao
, p. 1126 - 1136 (2007/10/03)
The development of efficient methods for the indole synthesis catalyzed by Cu(II) salts and its applications were investigated. Cu(OAc)2 has been proved to be the best catalyst for the synthesis of various 1-p-tolylsulfonyl or 1-methylsulfonylindoles, which have both electron-withdrawing and electron-donating groups on the aromatic ring and C2 position of indoles. For the primary aniline derivatives, Cu(OCOCF 3)2 showed good activities, while Cu(OAc)2 was a good catalyst for the cyclization of secondary anilines. This methodology could be applied to the sequential cyclization reaction for the compounds which have the electrophilic part in the same molecule. By prior treatment with KH, the sequential cyclization was realized to provide the tricyclic ring systems, but it was limited to five- and six-membered rings for the second cyclization. Finally, formal and total synthesis of hippadine with the Cu(II)-promoted indole synthesis as the key step was accomplished.
Efficient construction of indole rings from 2-ethynylaniline derivatives catalyzed by copper(II) salts and its application to the tandem cyclization reactions
Hiroya, Kou,Itoh, Shin,Ozawa, Mika,Kanamori, Yuichi,Sakamoto, Takao
, p. 1277 - 1280 (2007/10/03)
The efficient cyclization reactions of the N-methanesulfonyl or N-ethoxycarbonyl derivatives of 2-ethynylanilines, functionalized on the benzene ring and/or the acetylene terminal into indoles catalyzed by either Cu(OTf)2 or Cu(OAc)2 are accomplished. The application of this reaction to the tandem cyclization reaction is also described.
