959-66-0Relevant articles and documents
Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones
Daniliuc, Constantin,Glorius, Frank,Hu, Tianjiao,Lückemeier, Lukas
supporting information, p. 23193 - 23196 (2021/09/25)
Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.
1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: An Efficient Synthesis of 2-Quinolinones via β-Keto Amides
Vala, Anand,Parmar, Nirali,Soni, Jigar Y.,Kotturi, Sharadsrikar,Guduru, Ramakrishna
supporting information, p. 2080 - 2084 (2021/10/07)
Under thermal conditions, 1,4,2-dioxazol-5-ones are known to undergo decarboxylation followed by Lossen's rearrangement to yield isocyanates. Described herein is the in situ trapping of the resulting isocyanates with carbon nucleophiles to synthesize β-keto amides. Furthermore, a general and mild method for the conversion of the resulting β-keto amides into quinolin-2-ones is reported.
Palladium catalysed hydrolysis-free arylation of aliphatic nitriles for the synthesis of 4-arylquinolin-2-one/pyrazolone derivatives
Krishna Reddy, Singarajanahalli Mundarinti,Prasanna Kumari, Subramaniyan,Selva Ganesan, Subramaniapillai
, (2021/08/03)
Palladium catalysed addition of arylboronic acid to the readily available 2-cyano-(N-aryl)-acetamide or ethyl-2-cyanoacetate followed by subsequent reaction transform them into the biologically significant 4-arylquinolin-2-one or pyrazolone derivatives. The reaction conditions are robust enough to prevent the hydrolysis of ester/amide moiety during arylation. In addition, the unactivated nitrile moiety in the acetonitrile also converted to the corresponding acetophenone derivative.
Iron-catalyzed oxidative amidation of acylhydrazines with amines
Wang, Yi-Jie,Zhang, Guo-Yu,Shoberu, Adedamola,Zou, Jian-Ping
supporting information, (2021/08/18)
A new approach for amide bond formation via a mild and efficient Iron-catalyzed cross-coupling reaction of acylhydrazines and amines using TBHP as oxidant is described. This protocol is compatible with a wide range of amines and acylhydrazines. In addition, the synthetic application of the reaction is presented.
Chemoselective Cu-catalyzed synthesis of diverseN-arylindole carboxamides, β-oxo amides andN-arylindole-3-carbonitriles using diaryliodonium salts
Kumar Mehra, Manish,Malik, Monika,Kumar, Bintu,Kumar, Dalip
supporting information, p. 1109 - 1114 (2021/02/16)
Chemoselective copper-catalyzed synthesis of diverseN-arylindole-3-carboxamides, β-oxo amides andN-arylindole-3-carbonitriles from readily accessible indole-3-carbonitriles, α-cyano ketones and diaryliodonium salts has been developed. DiverseN-arylindole-3-carboxamides and β-oxo amides were successfully achieved in high yields under copper-catalyzed neutral reaction conditions, and the addition of an organic base (DIPEA) resulted in a completely different selectivity pattern to produceN-arylindole-3-carbonitriles. Moreover, the importance of the developed methodology was realized by the synthesis of indoloquinolones andN-((1H-indol-3-yl)methyl)aniline and by a single-step gram-scale synthesis of the naturally occurring cephalandole A analogue.
Catalyst- And Additive-Free Approach to Constructing Benzo-oxazine, Benzo-oxazepine, and Benzo-oxazocine: O Atom Transfer and C-O, C-N, and C-O Bond Formation at Room Temperature
Ghosh, Arnab,Hegde, Rajeev V.,Rode, Haridas B.,Ambre, Ram,Mane, Manoj V.,Patil, Siddappa A.,Sridhar, Balasubramanian,Dateer, Ramesh B.
supporting information, p. 8189 - 8193 (2021/11/01)
An exclusive synthesis of benzo-oxazine, benzo-oxazepine, and benzo-oxazocine from aryl propanal and 2-(hydroxyamino)phenyl alcohol under metal-free conditions is described. O atom transfer and formation of new C-O, C-N, and C-O bonds occur at room temperature to form six-, seven-, and eight-membered heterocycles under one-pot reaction conditions without using an external oxidant and base. The photophysical properties are studied using ultraviolet-visible absorption and photoluminescence. The mechanistic elucidation is well supported by control experiment and literature precedents.
Uses of ethyl benzoyl acetate for the synthesis of thiophene, pyran, and pyridine derivatives with antitumor activities
Ibrahim, Bishoy A.,Mohareb, Rafat M.
, p. 4023 - 4035 (2020/09/21)
The N-(arly)propanamide derivatives 3a,b were used for a series of heterocyclization reactions to give thiophene, pyran, and pyridine derivatives. Thus, these compounds underwent the Gewald's thiophene synthesis through their reactions with either malononitrile or ethyl cyanoacetate and elemental sulfur to afford compounds 6a-f, respectively. In addition, they were subjected through a series of multicomponent reactions (MCRs) to give pyran and fused derivatives. The reactions of 3a,b with either malononitrile or ethyl cyanoacetate gave pyridine derivatives 14a-d, respectively. The latter compounds afforded arylhydrazone derivatives 15a-m through their reactions with any of the aromatic diazonium salts 15a-c. The antitumor of the synthesized compounds against A549 (nonsmall cell lung cancer), H460 (human lung cancer), HT-29 (human colon cancer), and MKN-45 (human gastric cancer cancer) cancer cell lines together with foretinib as the positive control by a MTT assay was measured, and the results obtained showed that many compounds exhibited high potency against the six cancer cell lines.
Transition metal-free functionalized hydration of alkynes: One-pot synthesis of fluorinated β-keto-imidates using Selectfluor
Ghosh, Arnab,Hegde, Rajeev,Makane, Vitthal B.,Sridhar, Balasubramanian,Rode, Haridas B.,Patil, Siddappa A.,Dateer, Ramesh B.
supporting information, p. 4440 - 4445 (2019/05/16)
A transition metal-free, four-component one-pot synthesis of polyfunctionalized fluorinated β-keto-imidates via the functionalized hydration of alkynes has been described. The intermediate 1,3-ketoamino moiety was obtained from easily accessible arylpropioladehyde and arlyhydroxylamine and was treated with Selectfluor delivering fluorinated β-keto-imidates. A wide variety of functional groups are tolerated under mild reaction conditions and the product applicability is highlighted.
Catalytic Asymmetric Epoxidation of Aldehydes with Two VANOL-Derived Chiral Borate Catalysts
Gupta, Anil K.,Yin, Xiaopeng,Mukherjee, Munmun,Desai, Aman A.,Mohammadlou, Aliakbar,Jurewicz, Kelsee,Wulff, William D.
supporting information, p. 3361 - 3367 (2019/02/16)
A highly diastereo- and enantioselective method for the epoxidation of aldehydes with α-diazoacetamides has been developed with two different borate ester catalysts of VANOL. Both catalytic systems are general for aromatic, aliphatic, and acetylenic aldehydes, giving high yields and inductions for nearly all cases. One borate ester catalyst has two molecules of VANOL and the other only one VANOL. Catalysts generated from BINOL and VAPOL are ineffective catalysts. An application is shown for access to the side-chain of taxol.
Selective exploitation of acetoacetate carbonyl groups using imidazolium based ionic liquids: synthesis of 3-oxo-amides and substituted benzimidazoles
Chakraborty, Ankita,Majumdar, Swapan,Maiti, Dilip K.
, p. 3298 - 3302 (2016/07/11)
An unprecedented Br?nsted base ionic liquid tuned selective aminolysis of ester carbonyl of acetoacetates is demonstrated to achieve acetoacetamide derivatives. Other imidazolium ionic liquid performs an efficient cyclization catalysis involving acetoacetate-carbonyl groups and o-phenylenediamine at elevated temperature to produce benzimidazoles via C–C bond cleavage of intermediate 1,5-benzodiazepinones under solvent-free conditions.
