An earlier described three-component variant of the CastagnoliCushman reaction of homophthalic acid (via in situ cyclodehydration to the respective anhydride) was extended to involve hydroxylamine in lieu of the amine component of the reaction - Expression of TNF inhibitor in Senescence and Aging

An earlier described three-component variant of the CastagnoliCushman reaction of homophthalic acid (via in situ cyclodehydration to the respective anhydride) was extended to involve hydroxylamine in lieu of the amine component of the reaction. by the mole-ratio method. = 7.9, 1.4 Hz, 1H), 7.69 (td, = 7.6, 1.4 Hz, 1H), 7.51 (td, = 7.7, 1.0 Hz, 1H), 7.44C7.30 (m, 1H), 4.14 (s, 2H) [26]. 3.2.2. Slc7a7 Hydroxylamine Acetate Hydroxylamine hydrochloride (10.0 g, 144 mmol) was dissolved in deionized water (5 mL). The solution was added, on stirring, to a solution of sodium acetate (11.8 g, 144 mmol) in water (5 mL). The producing clear answer was concentrated to dryness. The solid residue was suspended in anhydrous methanol (20 mL) and filtered to remove sodium chloride. The filtrate was concentrated in vacuo to give hydroxylamine acetate (13.0 g, 141 mmol, 98%). 1H-NMR (400 MHz, DMSO-(7c). Yield 202 mg (52%); white powder, mp 214.3C214.7 C; 1H-NMR (400 MHz, DMSO-= 7.3 Hz, 2H, 2CH(Ar)), 7.46C7.33 (m, 5H, 5CH(Ar)), 7.29C7.10 (m, 3H, 3CH(Ar)), 6.78 (t, = 7.5 Hz, 1H, CH(Ar)), 6.66 (d, = 7.5 Hz, 1H, CH(Ar)), 5.89 (s, 1H, 3-H), 5.34C5.15 (m, 2H, CH2), 4.19 (s, 1H, 4-H). 13C-NMR (101 MHz, DMSO-calcd for C23H20NO5 [M + H]+ 412.1155, found 412.1149. (7d). Yield 208 mg (61%); white powder, mp 219.8C220.2 C. 1H-NMR (400 MHz, DMSO-= 7.0 Hz, 1H, CH(Ar)), 7.42 (p, = 7.4, 7.0 Hz, 1H, CH(Ar)), 7.49C7.36 (m, 2H, 2CH(Ar)). 7.30 (d, = 6.9 Hz, 1H, CH(Ar)), 6.73 (d, = 8.1 Hz, 1H, CH(Ar)), 6.61 (t, = 7.9 Hz, 1H, CH(Ar)), 6.20 (d, = 7.6 Hz, 1H, CH(Ar)), 5.72 (s, 1H, 3-H), 4.46C4.31 (m, 2H, CH2), 4.27 (t, = 4.0 Hz, 2H, CH2), 4.16 (s, 1H, CH, 4-H). 13C-NMR (101 MHz, DMSO-calcd for C18H16NO6 [M + H]+ 342.0972, found 342.0970. (7d). Yield 208 mg (61%); white powder, mp 219.8C220.2 C. 1H-NMR (400 MHz, DMSO-= 7.0 Hz, 1H, CH(Ar)), 7.42 (p, = 7.4, 7.0 Hz, 1H, CH(Ar)), 7.49C7.36 (m, 2H, 2CH(Ar)). 7.30 (d, = 6.9 Hz, 1H, CH(Ar)), 6.73 (d, = 8.1 Hz, 1H, CH(Ar)), 6.61 (t, = 7.9 Hz, 1H, CH(Ar)), 6.20 (d, = 7.6 Hz, 1H, CH(Ar)), 5.72 (s, 1H, 3-H), 4.46C4.31 (m, 2H, CH2), 4.27 (t, = 4.0 Hz, 2H, CH2), 4.16 (s, 1H, CH, 4-H). 13C-NMR (101 MHz, DMSO-calcd for C18H16NO6 [M + H]+ 342.0972, found 342.0970. (7e). Yield 239 mg (67%); white powder, mp 218.7C218.9 C; 1H-NMR (400 MHz, DMSO-= 7.3 Hz, 1H, CH(Ar)), 7.49C7.38 (m, 2H, 2CH(Ar)), 7.30 (d, = 7.2 Hz, 1H, CH(Ar)), 6.80 (s, Dicarbine 1H, CH(Ar)), 6.78 (d, = 8.4 Hz, 1H, CH(Ar)), 6.53 (d, = 8.2 Hz, 1H, CH(Ar)), 5.42 (s, 1H, 3-H), 4.28 (d, = 1.8 Dicarbine Hz, 1H, 4-H), 3.91 (q, = 6.9 Hz, 2H, CH2), 3.66 (s, 3H, OCH3), 1.26 (t, = 7.0 Hz, 3H, CH3). 13C-NMR (101 MHz, DMSO-calcd for C19H20NO6 [M Dicarbine + H]+ 358.1285, found 358.1300. (7f). Yield 212 mg (57%); white powder, mp 220.6C220.8 C; 1H-NMR (400 MHz, DMSO-= 7.4, 1.3 Hz, 1H, CH(Ar)), 7.51C7.39 (m, 2H, 2CH(Ar)), Dicarbine 7.31 (d, = 7.1 Hz, 1H, CH(Ar)), 6.44 (s, 2H, CH(Ar)), 5.44 (s, 1H, 3-H), 4.33 (s, 1H, 4-H), 3.63 (s, 6H, 2OCH3), 3.58 (s, 3H, OCH3). 13C-NMR (101 MHz, DMSO-calcd for C19H20NO7 [M + H]+ 374.1234, found 374.1244 (7g). Yield 154 mg (45%); white powder, mp 224.3C224.6 C; 1H-NMR (400 MHz, DMSO-= 7.1 Hz, 1H, CH(Ar)), 7.50C7.36 (m, 2H, 2CH(Ar)), 7.29 (d, = 7.1 Hz, 1H, CH(Ar)), 6.80 (s, 1H, CH(Ar)) 6.79 (d, = 8.2 Hz, 1H, CH(Ar)), 6.54 (d, = 9.6 Hz, 1H, CH(Ar)), 5.42 (s, 1H, 4-H), 4.28 (s, 1H, 3-H), 3.66 (s, 3H, OCH3), 3.65 (s, 3H, OCH3). 13C-NMR (101 MHz, DMSO-177.1, 165.5, 153.9, 153.4, 138.4, 137.0, 136.1, 135.0, 133.8, 133.0, 131.66, 123.1, 116.7, 115.4, 70.0, 60.6, 60.6, 56.7. HRMS (ESI), calcd for C18H18NO6 [M + H]+ 344.1129, found 344.1141. (7h). Yield 205 mg (60%); white powder, mp 208.2C208.7 C; 1H-NMR (400 MHz, DMSO-= 7.7, 6.6, 3.9 Hz, 2H, 2CH(Ar)), 7.26 (dd, = 5.8, 2.8 Hz, 1H, CH(Ar)), 6.59 (d, = 2.2 Hz, 1H, CH(Ar)), 6.50 (d, = 8.5 Hz, 1H, CH(Ar)), 6.33 (dd, = 8.5, 2.2 Hz, 1H, CH(Ar)), 5.66 (s, 1H, 4-H), 4.05 (s, 1H, 3-H), 3.86 (s, 3H, OCH3), 3.68 (s, 3H, OCH3). 13C-NMR (101 MHz, DMSO-(7i). This product was isolated after washing the precipitate from r.m. with Et2O and filtration. Yield 235 mg (54%); white powder, mp 211.6C211.9 C; 1H-NMR (400 MHz, DMSO-= 8.9 Hz, 1H, CH(Ar)), 6.77 (dd, = 8.9, 3.0 Hz, 1H, CH(Ar)), 6.19 (d, = 2.7 Hz,.

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