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ChemicalBook CAS DataBase List 5,8-dioxo-6-(pyridin-3-ylamino)naphthalene-1-sulfonamide

5,8-dioxo-6-(pyridin-3-ylamino)naphthalene-1-sulfonamide synthesis

3synthesis methods
1309647-27-5 Synthesis
1-Naphthalenesulfonamide, 5,8-dihydro-5,8-dioxo-

1309647-27-5
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5,8-dioxo-6-(pyridin-3-ylamino)naphthalene-1-sulfonamide

1436382-03-4
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Yield:1436382-03-4 87%

Reaction Conditions:

with copper(II) acetate monohydrate in acetic acid;trifluoroacetic acid at 50;Reflux;regioselective reaction;

Steps:

4.1 4.5 General procedure of C-N coupling reaction of ring-opening 6-amino/aniline-naphthalene-5,8-dione-1-sulfonamides

General procedure: Compound 1 (237 mg, 1 mmol), amine (1.2 mmol), and Cu(OAc)2·H2O (40 mg, 0.2 mmol) were solubilized by gently warming TFA and AcOH co-solvent (0.5 mL/5 mL, v/v), at 50 °C to reflux, monitored by TLC. After compound 1 was completely consumed, all the volatiles were removed in vacuo to give crude products, which were purified by flash chromatography on silica gel and recrystallized in EtOH/H2O (v/v: 1/2) or THF/H2O (1/2 v/v) to afford the ring-opening derivatives 3a-g.

References:

Yu, Wenying;Li, Chenglong [Tetrahedron,2014,vol. 70,# 2,p. 459 - 464]