52190-13-3Relevant academic research and scientific papers
Electrochemical dehydrogenative cyclization of 1,3-dicarbonyl compounds
Wu, Zheng-Jian,Li, Shi-Rui,Long, Hao,Xu, Hai-Chao
, p. 4601 - 4604 (2018)
The intramolecular C(sp3)-H/C(sp2)-H cross-coupling of 1,3-dicarbonyl compounds has been achieved through Cp2Fe-catalyzed electrochemical oxidation. The key to the success of these dehydrogenative cyclization reactions is
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).
A copper(II)-mediated radical cross-dehydrogenative coupling/sulfinic acid elimination approach to 2-quinolones
Gorman, Ryan M.,Hurst, Timothy E.,Petersen, Wade F.,Taylor, Richard J.K.
, (2019/11/19)
A new cyclisation procedure to prepare 4-carboxy-quinolin-2-ones via a one-pot Cu(II)-mediated radical cross-dehydrogenative coupling/sulfinic acid elimination of linear anilides is described. Extensions to more complex substrates are also reported as are
Site-Selective Conversion of Azido Groups at Carbonyl α-Positions to Diazo Groups in Diazido and Triazido Compounds
Yokoi, Taiki,Tanimoto, Hiroki,Ueda, Tomomi,Morimoto, Tsumoru,Kakiuchi, Kiyomi
, p. 12103 - 12121 (2018/10/09)
This paper reports on the selective conversion of alkyl azido groups at the carbonyl α-position to diazo compounds. Through β-elimination of dinitrogen, followed by hydrazone formation/decomposition, α-azidocarbonyl moieties were transformed into α-diazo carbonyl groups in one step. As these reaction conditions do not involve aryl or general alkyl azides, site-selective conversions of di- and triazides were achieved. Through this method, the successive site-selective conjugation of the triazido molecule with three different components is demonstrated.
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
A Direct C-H/Ar-H Coupling Approach to Oxindoles, Thio-oxindoles, 3,4-Dihydro-1 H-quinolin-2-ones, and 1,2,3,4-Tetrahydroquinolines
Hurst, Timothy E.,Gorman, Ryan M.,Drouhin, Pauline,Perry, Alexis,Taylor, Richard J. K.
supporting information, p. 14063 - 14073 (2016/02/18)
A copper(II)-catalysed approach to oxindoles, thio-oxindoles, 3,4-dihydro-1H-quinolin-2-ones, and 1,2,3,4-tetrahydroquinolines via formal C-H, Ar-H coupling is described. In a new variant, copper(II) 2-ethylhexanoate has been identified as an inexpensive and efficient catalyst for this transformation, which utilises atmospheric oxygen as the re-oxidant. Copper(II) 2-ethylhexanoate: The synthesis of oxindoles, thio-oxindoles, 3,4-dihydro-1H-quinolin-2-ones, and 1,2,3,4-tetrahydroquinolines from linear precursors by direct C-H, Ar-H coupling by using a single copper catalyst is reported (see scheme; DIPEA=diisopropylethylamine, EWG=electron-withdrawing group). The cyclisations are simple to perform, run open to the air, are moisture insensitive, and use an inexpensive catalyst.
Rh(II)-catalyzed intramolecular C-H insertion of diazo substrates in water: Scope and limitations
Candeias, Nuno R.,Gois, Pedro M. P.,Afonso, Carlos A. M.
, p. 5489 - 5497 (2007/10/03)
Preferential Rh(II) carbenoid intramolecular C-H versus O-H insertion derived from α-diazo-acetamides can be achieved in water by using an appropriate combination of the catalyst and amide groups, which creates a larger hydrophobic environment around the
Cycloadditions, 14. - Intramolecular Diels-Alder Reactions of Allenecarboxanilides; Competition of the Anilino Nucleus with "Benzylic-Bonded" Arenes and Heteroarenes
Schlindwein, Hans-Juergen,Diehl, Klaus,Himbert, Gerhard
, p. 577 - 584 (2007/10/02)
The N-(arylmethyl)- and N-(hetarylmethyl)allenecarboxanilides 6a-c and 6d-f, resp., are synthesized by the ylide route.Heating these allenes furnishes either the tricycles 7a, b and d (Ar = phenyl, 1-naphthyl and 2-thienyl) or the oxatricycles 10a, b by i
New Neutral Ionophores with High Ba2+ Selectivity
Kleiner, Thomas,Bongardt, Frank,Voegtle, Fritz,Laeubli, Markus Werner,Dinten, Oliver,Simon, Wilhelm
, p. 1071 - 1077 (2007/10/02)
The syntheses and the selectivity coefficients of the new open-chained, electrically neutral ionophores 2 - 4 are reported.Their lipophilicities and their selectivities in membranes with respect to Ba2+ ions were optimized: 2c and - to a smalle
Neutral Ionophores with Selectivity for Na+
Voegtle, Fritz,Kleiner, Thomas,Leppkes, Reinhard,Laeubli, Markus Werner,Ammann, Daniel,Simon, Wilhelm
, p. 2028 - 2034 (2007/10/02)
New non-macrocyclic, electrically neutral ionophores 5 - 9 are described.In membranes they induce selectivities of Na+ over K+ by a factor of up to 20.
