195073-95-1Relevant academic research and scientific papers
An efficient and rapid intramolecular aza-Michael addition of 2′-aminochalcones using ionic liquids as recyclable reaction media
Chelghoum,Bahnous,Bouraiou,Bouacida,Belfaitah
, p. 4059 - 4061 (2012)
A new, convenient, and efficient method for the intramolecular aza-Michael addition reaction of 2′-aminochalcones is developed using 1-n-butyl-3-methylimidazolium tetrafluoroborate as the solvent and catalyst. The ionic liquid is successfully regenerated and reused.
Copper-Catalyzed Chemoselective Cyclization Reaction of 2-Isocyanoacetophenone: Synthesis of 4-Hydroxyquinoline Compounds
Yuan, Qing,Rao, Weidong,Wang, Shun-Yi,Ji, Shun-Jun
, p. 1279 - 1284 (2020/01/22)
A copper-catalyzed intramolecular cyclization reaction of 2-isocyanoacetophenone derivatives to afford 4-hydroxyquinolines chemoselectively is described. The transformation proceeds through enol tautomerism and a subsequent C-C bond formation. Compared to previous methods, this study provides a new protocol for the construction of 4-hydroxyquinoline compounds from functionalized isocyanides under mild conditions.
Tandem Access to Acridones and their Fused Derivatives: [1+2+3] Annulation of Isocyanides with Unsaturated Carbonyls
Zhang, Ling-Juan,Yang, Wenhui,Hu, Zhongyan,Zhang, Xian-Ming,Xu, Xianxiu
supporting information, p. 2379 - 2384 (2020/02/05)
A wide range of acridones and their cyclo[b]-fused derivatives are efficiently constructed by a double annulation of o-enoyl arylisocyanides with α, β-unsaturated carbonyls under simple metal-free condition. This protocol is general, efficient and practical, featuring the successive formation of two rings by a one-pot domino transformation. A tandem process involing an isocyanide-based [1+4] cycloaddition, an aminofuran-based intramolecular [4+2] cycloaddition, ring opening and aromatization is proposed for the transformation. (Figure presented.).
Cyclopropyl carbinol rearrangement for benzo-fused nitrogen ring synthesis
Kothandaraman, Prasath,Huang, Chuhui,Susanti, Dewi,Rao, Weidong,Chan, Philip Wai Hong
supporting information; experimental part, p. 10081 - 10088 (2011/10/09)
A synthetic method that relies on gold-catalysed cyclopropyl carbinol rearrangement of 2-tosylaminophenyl cyclopropylmethanols to prepare 2,3-dihydro-1H-benzo[b]azepines and 2-vinylindolines efficiently is reported. The reactions were shown to be chemoselective, with secondary and tertiary alcohol substrates exclusively providing benzo-fused five- and seven-membered ring products, respectively. The ring-forming process was also found to proceed in moderate to excellent yields under mild conditions only in the presence of the gold and silver catalyst combination. The mechanism is thought to involve activation of the alcohol by the (p-CF3C6H 4)3PAuCl/AgOTf (Tf=triflate) catalyst, resulting in ionization of the starting material. The tertiary carbocationic intermediate generated in situ in this manner then triggers ring-opening of the cyclopropane moiety and trapping by the tethered aniline group to give the 2,3-dihydro-1H-benzo[b]azepine. Cyclopropane ring fragmentation of the secondary carbocationic analogue, on the other hand, results in diene formation followed by subsequent intramolecular hydroamination to afford the 2-vinylindoline. Copyright
