Assembly of fluorinated benzodiazepines via Rh(iii)-catalysed [5+2] annulation of N-benzo[d]imidazole indolines with 2,2-difluorovinyl tosylate

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(27), P. 12589 - 12594

Published: Jan. 1, 2023

Solvent-tunable Rh( iii )-catalysed C–H activation/[5+2] annulation of N -benzo[ d ]imidazole indolines with 2,2-difluorovinyl tosylate was realized for building monofluorinated and gem -difluorinated benzodiazepines.

Language: Английский

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1,3‐Benzenedicarbonitrile, 2,4,5,6‐Tetrakis(diphenylamino)‐

Encyclopedia of Reagents for Organic Synthesis, Journal Year: 2023, Volume and Issue: unknown, P. 1 - 3

Published: Jan. 13, 2023

[1846598-27-3] C56H40N6 (MW 796.96) InChI = 1S/C56H40N6/c57-41-51-53(59(43-25-9-1-10-26-43)44-27-11-2-12-28-44)52(42-58)55(61(47-33-17-5-18-34-47)48-35-19-6-20-36-48)56(62(49-37-21-7-22-38-49)50-39-23-8-24-40-50)54(51)60(45-29-13-3-14-30-45)46-31-15-4-16-32-46/h1-40H InChIKey ZOMQCVKHGOMNER-UHFFFAOYSA-N (reagent used as an organic photoredox catalyst1) Alternative Names: 4DPAIPN, 2,4,5,6-tetrakis(diphenylamino)-1,3-benzenedicarbonitrile, 2,4,5,6-tetrakis(diphenylamino)isophthalonitrile, 1,3-dicyano-2,4,5,6-tetrakis(N,N-diphenylamino)benzene. Physical Data: absorption λmax 405 nm,2 redox potentials (vs. SCE, saturated calomel electrode, 0 V in CH3CN); −1.65 (P/P–), +0.90 (P*/P–), +1.03 (P+/P), −1.52 (P+/P*).3 Solubility: soluble CH3CN, CHCl3, CH2Cl2, DMF, and DMSO; insoluble H2O. Form Supplied in: yellow to yellow/brown solid. Preparative Methods: prepared via deprotonation of diphenylamine (5–6 equiv) the presence NaH (7–8 DMF at 50–60 °C for 1 h, followed by addition 2,4,5,6-tetrafluoroisophthalonitrile (1 stirring 40–50 4–16 h. Quenching with isopropanol/water causes crude product precipitate.2,3 Purification: recrystallization from CH2Cl2/pentane/hexanes; silica gel chromatography (eluting CH2Cl2/hexanes). Handling, Storage, Precautions: avoid contact skin eyes. Store a cool, dry, dark place.

Language: Английский

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Synthesis of 5-Fluoroindolizines by Photocatalytic Defluorinative Coupling and SNV Cyclization

Synfacts, Journal Year: 2022, Volume and Issue: 18(06), P. 0604 - 0604

Published: May 17, 2022

Key words fluoroindolizines - photocatalysis C–F bond cleavage pyrrolylacetic acids

Language: Английский

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