838828-39-0Relevant articles and documents
Diastereoselective Nickel-Catalyzed Carboiodination Generating Six-Membered Nitrogen-Based Heterocycles
Marchese, Austin D.,Kersting, Louise,Lautens, Mark
supporting information, p. 7163 - 7168 (2019/09/12)
A scalable, diastereoselective nickel-catalyzed carboiodination reaction is reported that avoids metal-based reducing agents. Novel anti-dihydroquinolones and previously unreported tetrahydroquinolines are now readily prepared. The generation of anti-dihydroquinolones is noteworthy, as this selectivity is opposite to that of the Pd variant. Mechanistic insight into the nature of the nickel-catalyzed carboiodination reaction was derived experimentally, suggesting a catalyst-controlled cyclization and stereoretentive reductive elimination.
Bis(dibenzylideneacetone)palladium(0)/tert-Butyl Nitrite- Catalyzed Cyclization of o-Alkynylanilines with tert-Butyl Nitrite: Synthesis and Applications of Indazole 2-Oxides
Senadi, Gopal Chandru,Wang, Ji-Qi,Gore, Babasaheb Sopan,Wang, Jeh-Jeng
supporting information, p. 2747 - 2753 (2017/08/23)
An efficient method for the synthesis of 1-benzyl/arylindazole 2-oxides via a bis(dibenzylideneacetone)palladium(0) [Pd(dba)2]/tert-butyl nitrite (TBN)-catalyzed reaction of o-alkynylaniline derivatives with TBN is reported. The overall transfo
Scaffold-divergent synthesis of ring-fused indoles, quinolines, and quinolones via iodonium-induced reaction cascades
Halim, Rosliana,Aurelio, Luigi,Scammells, Peter J.,Flynn, Bernard L.
, p. 4708 - 4718 (2013/06/27)
N-(2-Iodophenyl)imines A are readily formed from Schiff's base condensation of 2-iodoanilines with carbonyls and ketals. These imines provide useful substrates in scaffold-divergent synthesis through the attachment of an alkyne (Songashira coupling or acyl substitution of a Weinreb amide) followed by an iodonium-induced reaction cascade to give ring-fused indoles B, quinolines C, or quinolones D depending on the reaction conditions employed.
Potassium tert-butoxide promoted intramolecular arylation via a radical pathway
Roman, Daniela Sustac,Takahashi, Yoko,Charette, Andre B.
supporting information; experimental part, p. 3242 - 3245 (2011/08/02)
Potassium tert-butoxide mediated intramolecular cyclization of aryl ethers, amines, and amides was efficiently performed under microwave irradiation to provide the corresponding products in high regioisomeric ratios. The reaction proceeds via single-electron transfer to initiate the formation of an aryl radical, followed by a kinetically favored 5-exo-trig and subsequent ring expansion.
Alternating lodonium-mediated reaction cascades giving indole- And quinoline-containing polycycles
Halim, Rosliana,Scammells, Peter J.,Flynn, Bernard L.
supporting information; experimental part, p. 1967 - 1970 (2009/04/10)
A simple two-step convergent protocol gives direct access to synthetic Intermediate A from ortho-iodoanilines. Intermediate A can be treated with NIS In CH2CI2 to Induce novel lodonium mediated domino reaction cascade, which provides direct access to ring-fused Indole compounds B. Simply by changing the reaction conditions, this protocol can be directed down an alternative domino reaction cascade to give various ring fused quinoline compounds C.
