Carbonylative synthesis and functionalization of indoles

• Alex De Salvo,
• Raffaella Mancuso and
• Xiao-Feng Wu

Beilstein J. Org. Chem. 2024, 20, 973–1000, doi:10.3762/bjoc.20.87

• controllable and regioselective synthesis of indol-3-α-ketoamides and indol-3-amides via the direct double- and monoaminocarbonylation of indole derivatives by using secondary amines [70]. They used Pd(dppf)Cl2 as catalyst system. The indol-3-α-ketoamides were synthesized by adding dppf as ligand, CuI as co

• . Synthesis of N-methylindole-3-carboxylates from N-methylindoles and phenols through metal-catalyst-free reaction (top) and its hypothesized mechanism (bottom). Synthesis of indol-3-α-ketoamides (top) and indol-3-amides (bottom) via direct double- and monoaminocarbonylation of indole derivatives with

Recent advances in organocatalytic asymmetric aza-Michael reactions of amines and amides

• Pratibha Sharma,
• Raakhi Gupta and
• Raj K. Bansal

Beilstein J. Org. Chem. 2021, 17, 2585–2610, doi:10.3762/bjoc.17.173

• . accomplished an asymmetric organocatalytic quadruple cascade reaction of various α-ketoamides 111 with aromatic α,β-unsaturated aldehydes 112 to obtain tetraaryl-substituted 2-azabicyclo[3.3.0]octadienones 114 in good yields (34–71%) with excellent diastereo- and enantioselectivities (84–97%). The reaction

Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis

• Flavio Fanelli,
• Giovanna Parisi,
• Leonardo Degennaro and
• Renzo Luisi

Beilstein J. Org. Chem. 2017, 13, 520–542, doi:10.3762/bjoc.13.51

•  1). The use of an integrated microflow system allowed the preparation of functionalized α-ketoamides by a three-component reaction between carbamoyllithium, methyl chloroformate and organolithium compounds bearing sensitive functional groups (i.e., NO2, COOR, epoxide, carbonyl) (Scheme 2). It should

• production and formulation of APIs. (Reproduced with permission from [85], copyright 2016 American Association for the Advancement of Science). A flow microreactor system for the generation and trapping of highly unstable carbamoyllithium species. Flow synthesis of functionalized α-ketoamides. Reactions of

Three-component synthesis of highly functionalized aziridines containing a peptide side chain and their one-step transformation into β-functionalized α-ketoamides

• Lena Huck,
• Juan F. González,
• Elena de la Cuesta and
• J. Carlos Menéndez

Beilstein J. Org. Chem. 2016, 12, 1772–1777, doi:10.3762/bjoc.12.166

• . Their transformation into β-trifluoroacetamido-α-ketoamide and α,β-diketoamide frameworks was also achieved in a single step. Keywords: α-ketoamides; aziridines; multicomponent reactions; nitrogen heterocycles; one-pot reactions; peptide mimics; vicinal tricarbonyl compounds; Introduction Aziridine

• compounds into functionalized β-amino-α-ketoamides. This is an important structural fragment that is used in the design of reversible covalent enzyme inhibitors, including the anti-hepatitis C drugs boceprevir and telaprevir, because the electrophilic keto group is able to react reversibly with mercapto or

• proceeds under mild and functional group-tolerant conditions, allowing the synthesis of N-unprotected, trisubstituted aziridines bearing a peptide side chain. The synthetic application of these aziridines was demonstrated by their one-pot transformation into β-trifluoroacetamido-α-ketoamides, thus

Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update

• Bin Yu,
• Hui Xing,
• De-Quan Yu and
• Hong-Min Liu

Beilstein J. Org. Chem. 2016, 12, 1000–1039, doi:10.3762/bjoc.12.98

• Recently, iridium has emerged as a powerful catalyst for C–H bond functionalization [20][21][22][23]. In 2014, Yamamoto and co-workers reported a cationic iridium complex catalyzed asymmetric intramolecular hydroarylation of α-ketoamides, yielding 3-substituted 3-hydroxy-2-oxindoles with high

• regioselectivities and enantioselectivities (up to 98% ee, Scheme 7) [24]. The reactions were performed in 1,2-dimethoxyethane using 5 mol % of [Ir(cod)2](BArF4) as the catalyst and 5.5 mol % of the chiral ligand L4. A wide range of aromatic and aliphatic α-ketoamides were tolerated under the optimized conditions. A

An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y

• Suresh Babu Meruva,
• Akula Raghunadh,
• Raghavendra Rao Kamaraju,
• U. K. Syam Kumar and
• P. K. Dubey

Beilstein J. Org. Chem. 2014, 10, 471–480, doi:10.3762/bjoc.10.45

• . The oxidative amidation Bischler–Napieralski reaction provides a simple and direct method for the synthesis of carbolines, which are otherwise synthesized by multistage reactions utilizing starting materials which are not readily available. Experimental General procedure for the synthesis of α

• -ketoamides (9a–9j) A mixture of 2,2-dibromo-1-phenylethanone (11a, 6.0 g, 21.6 mmol) and sodium iodide (6.48 g, 43.2 mmol) in dimethyl sulfoxide (30.0 mL) at 25–45 °C was stirred for 40–50 minutes. Triethylamine (6.55 g, 64.8 mmol) and tryptamine (10, 3.45 g, 21.6 mmol) were then added to the mixture under a