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

• time, Wu and co-workers contributed to the introduction of two new syntheses of N-aroylindole derivatives by means of nickel catalysis. In 2021, they reported a nickel-catalyzed carbonylative cyclization of 2-nitroalkynes and aryl iodides with Co2(CO)8 as the CO source. The reaction was performed in

•  28). Metal-catalyzed carbonylative cyclization reaction of indole derivatives In 2016, Guo and co-workers, in the same work in which different examples of 6H-isoindolo[2,1-a]indol-6-ones were reported, performed the synthesis of indeno[1,2-b]indol-10(5H)-ones from 2-(2-bromophenyl)-1-alkyl-1H-indoles

• [55] under the same conditions as mentioned in Scheme 25. The presence of an alkyl group on the indole nitrogen led to a Heck cyclization instead of a cycloaminocarbonylation (Scheme 29). In 2019, two different groups independently reported a carbonylative cyclization of o-indolylarylamines. In

Metal-catalyzed coupling/carbonylative cyclizations for accessing dibenzodiazepinones: an expedient route to clozapine and other drugs

• Amina Moutayakine and
• Anthony J. Burke

Beilstein J. Org. Chem. 2024, 20, 193–204, doi:10.3762/bjoc.20.19

• ; carbonylative cyclization; Chan–Lam; nitrogen heterocycle; one-pot; Introduction Dibenzodiazepine units are without doubt highly privileged structures, endowed with numerous medicinally relevant properties, and notably include anti-anxiolytic and antidepressant activities. These scaffolds have received much

• not been reported previously (the methods a–c indicated in Scheme 1 have a different route, and none involve either a Chan–Lam or carbonylative cyclization). For the sake of health and safety, and given that our infrastructures did not permit the use of molecular CO, we felt more secure with a

• screened. The reaction was carried out in the presence of acetic anhydride (Ac2O) as an activator, but unfortunately, no DBDAP was obtained (entry 9, Table 1). The use of triphosgene as the CO transfer agent failed to give any product. When we undertook the B–H amination/carbonylative cyclization of o

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

• Yordanka Mollova-Sapundzhieva,
• Plamen Angelov,
• Danail Georgiev and
• Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

• of methods for their synthesis is a very active area of research. Recent contributions to the synthesis of 4-quinolones made use of phosphine-mediated redox cyclization of 1-(2-nitroaryl)prop-2-ynones [39], palladium-catalyzed carbonylative cyclization of 2-bromonitrobenzenes and alkynes [40], TsCl

Iron-catalyzed domino coupling reactions of π-systems

• Austin Pounder and
• William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

• heteroarenes were all well-tolerated; however, monosubstituted aryl rings suffered from low regioselectivity which is in accordance with HAS-type reactions [138]. In 2020, the Wu group expanded on the radical cyclization chemistry of γ,δ-unsaturated oxime esters, describing a carbonylative cyclization with

KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones

• Qiao Lin,
• Shiling Zhang and
• Bin Li

Beilstein J. Org. Chem. 2020, 16, 492–501, doi:10.3762/bjoc.16.44

• reactions using potassium tert-butoxide as promoter. Wu developed an efficient protocol for the KOt-Bu-promoted synthesis of 1-aminoisoquinolines from 2-methylbenzonitriles and benzonitriles [23], and the carbonylative cyclization of propargylic amines with selenium under CO gas-free conditions [24]. Based

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• the carbonylative cyclization reaction of carboxylic acid methyl and ethyl esters 42 which led to the formation of 1-indanones 43 [33]. This reaction was carried out in acetonitrile, in the presence of triethylamine, under carbon monoxide atmosphere, achieving efficiency in the range of 88–92%, when

Amines as key building blocks in Pd-assisted multicomponent processes

• Didier Bouyssi,
• Nuno Monteiro and
• Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

• , the Pd-mediated three-component reaction that gives access to the alkenylboronate 80 was followed by a palladium-mediated carbonylative cyclization reaction. Hydrogenation of the resulting unsaturated lactam 81 and removal of the N-benzyl group afforded rolipram (Scheme 34). Alper and coworkers

Radical carbonylations using a continuous microflow system

• Takahide Fukuyama,
• Md. Taifur Rahman,
• Naoya Kamata and
• Ilhyong Ryu

Beilstein J. Org. Chem. 2009, 5, No. 34, doi:10.3762/bjoc.5.34

• pressurized carbon monoxide gas. Good to excellent yields of carbonylated products were obtained via radical formylation, carbonylative cyclization and three-component coupling reactions, using tributyltin hydride or TTMSS as a radical mediator. Keywords: continuous flow system; microreactor; radical

• carbonylation has a wide range of applications including carbonylative cyclization and multi-component coupling reactions. In this regard, we again chose stannylcarbonylation using 1,6-azaenyne 7 as a model for cyclization [22][23]. Using a similar microflow system but with an extended reaction time, we were