Synthesis of substituted diazino[c]quinolin-5(6H)-ones, diazino[c]isoquinolin-6(5H)-ones, diazino[c]naphthyridin-6(5H)-ones and diazino[c]naphthyridin-5(6H)-ones

Fresneau, Nathalie; Cailly, Thomas; Fabis, Frédéric; Bouillon, Jean‐Philippe

doi:10.1016/j.tet.2013.04.104

Cited by 7 publications

(4 citation statements)

References 35 publications

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“…IR (cm –1 , thin film) 1005, 760; 1 H NMR (400 MHz, d 6 -DMSO) δ 7.50 (1H, t J = 4 Hz), 7.47–7.41 (1H, m), 7.13 (1H, t J = 9 Hz) ppm; 19 F NMR (400 MHz, d 6 -DMSO δ −107.0 ppm. Data are in accordance with literature …”

Section: Methodssupporting

confidence: 89%

Design and Application of a Low-Temperature Continuous Flow Chemistry Platform

Newby

Blaylock

Witt

et al. 2014

Org. Process Res. Dev.

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A flow reactor platform technology applicable to a broad range of low temperature chemistry is reported. The newly developed system captures the essence of running low temperature reactions in batch and represents this as a series of five flow coils, each with independently variable volume. The system was initially applied to the functionalization of alkynes, Grignard addition reactions, heterocycle functionalization, and heteroatom acetylation. This new platform has then been used in the preparation of a 20-compound library of polysubstituted, fluorine-containing aromatic substrates from a sequential metalationquench procedure and can be readily adapted to provide gaseous electrophile inputs such as carbon dioxide using a tube-in-tube reactor.

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Section: Methodssupporting

confidence: 89%

Design and Application of a Low-Temperature Continuous Flow Chemistry Platform

Newby

Blaylock

Witt

et al. 2014

Org. Process Res. Dev.

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show abstract

“…Starting from 2-chloro-3-cyanopyrazine (502 mg, 3.60 mmol) and 2,5-difluorophenylboronic acid [42] (855 mg, 5.41 mmol) following general procedure A, refluxing the reaction overnight and using PE/EtOAc (85:15) as eluent for the chromatography, 7 was obtained as a yellow solid …”

Section: -Cyano-3-(25-difluorophenyl)pyrazine (7)mentioning

confidence: 99%

“…2-Amino-3-chloropyrazine (156 mg, 1.20 mmol) and ethyl 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate [42] (306 mg, 3.60 mmol) were dissolved in a mixture of dioxane/water 12:1 (9.2 mL), then K 3 PO 4 (764 mg, 3.60 mmol) and Pd(PPh 3 ) 4 (111 mg, 8 mol%) were added. The reaction mixture was refluxed overnight, cooled to room temperature and evaporated to dryness.…”

Section: -(1-propylpiperidin-4-yl)methyloxypyrazino[23-c]isoquinolimentioning

confidence: 99%

“…The resulting solution was heated at 80 °C for 10 min. A solution of N-(4-(tri(n-butyl)stannyl)pyridazin-3-yl)pivalamide [42] (260 mg, 0.54 mmol) in dry toluene (1.6 mL) and ethyl 2-iodobenzoate (120 μL, 0.80 mmol) were successively added. The solution was refluxed overnight and the resulting mixture was evaporated to dryness.…”

Section: -(1-propylpiperidin-4-yl)methyloxypyridazino[34-c]isoquinomentioning

confidence: 99%

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