876061-22-2Relevant academic research and scientific papers
Synthesis of Oxindole Derivatives via Intramolecular C–H Insertion of Diazoamides Using Ru(II)-Pheox Catalyst
Phan Thi Thanh, Nga,Dang Thi Thu, Huong,Tone, Masaya,Inoue, Hayato,Iwasa, Seiji
, (2020/10/02)
This work presented the efficient intramolecular aromatic C–H insertion of diazoacetamide. The 1a–1o diazo compounds (except for 1k) were converted into their corresponding oxindoles via an intramolecular C–H insertion reaction in the presence of a Ru catalyst. The Ru-Pheox catalyst was shown to be highly efficient in this transformation in terms of the regioselectivity, producing the desired products in excellent yield (99%). The efficiency of the Ru catalyst reached 580 (TON) and 156 min?1 (TOF).
Expedient Access to 2-Benzazepines by Palladium-Catalyzed C?H Activation: Identification of a Unique Hsp90 Inhibitor Scaffold
Virelli, Matteo,Moroni, Elisabetta,Colombo, Giorgio,Fiengo, Lorenzo,Porta, Alessio,Ackermann, Lutz,Zanoni, Giuseppe
supporting information, p. 16516 - 16520 (2018/10/25)
Bioactive 2-benzazepines were accessed in an atom- and step-economical manner through a versatile palladium-catalyzed C?H activation strategy. The C?H arylation required low catalyst loading and a mild base, which was reflected by a broad scope and high functional-group tolerance. The benzotriazolodiazepinones were identified as new heat shock protein 90 (Hsp90) inhibiting lead compounds, with considerable potential for anti-cancer applications.
Transition-Metal-Free Fluoroarylation of Diazoacetamides: A Complementary Approach to 3-Fluorooxindoles
Dong, Kuiyong,Yan, Bin,Chang, Sailan,Chi, Yongjian,Qiu, Lihua,Xu, Xinfang
, p. 6887 - 6892 (2016/08/16)
An efficient transition-metal-free fluoroarylation reaction of N-aryl diazoacetamides with NFSI (N-fluorobenzenesulfonimide) is described. This reaction directly provides 3-fluorooxindole derivatives in yields of 67-93% with high selectivity via a carbene
Solid-phase approach to tetrahydroquinolones using a sulfur linker cleaved by SmI2
Turner, Kristy L.,Baker, Thomas M.,Islam, Saidul,Procter, David J.,Stefaniak, Mark
, p. 329 - 332 (2007/10/03)
A sulfur α-heteroatom-substituted carbonyl (HASC) linker has been utilized in a solid-phase approach to tetrahydroquinolones. The route illustrates the compatibility of the linker system with palladium-catalyzed transformations and its utility for library synthesis. The linker is cleaved by electron transfer from samarium(II) iodide.
Solid phase approaches to N-heterocycles using a sulfur linker cleaved by SmI2
McAllister, Laura A.,Turner, Kristy L.,Brand, Stephen,Stefaniak, Mark,Procter, David J.
, p. 6497 - 6507 (2007/10/03)
A sulfur HASC (α-hetero-atom substituted carbonyl) linker has been utilized in solid-phase approaches to oxindoles and tetrahydroquinolones. The route to oxindoles employs the first Pummerer cyclizations on solid phase, whereas the route to tetrahydroquinolones involves a microwave-assisted Heck reaction followed by a Michael cyclization. In both cases, the linker is cleaved in a traceless fashion by electron transfer from samarium(II) iodide. The routes illustrate the compatibility of the linker system with a number of reaction types and its utility for library synthesis.
