Furazans and furazan oxides. 7. Interconversions of anthranils, benzofurazan oxides, and indazoles

Abstract

Barcza for helpful discussions and also his staff for providing the spectral and analytical data. We are indebted to Dr. Renate Coombs and her staff for recording the mass spectra.

Synthesis and complexing properties of macrocycles incorporating 2,2'-biindazolyl binding subunits

“…By this method, 7,7'-dinitro-2,2,-biindazole (4) was obtained in a 73% overall yield, instead of the 13% reported by Boulton from the same aldehyde 2 (Scheme I). 11 In agreement with the Krbechek results, a mixture of indazole 24 and biindazole 22 was obtained when the azine 17 was heated for 1 h at 150 °C. 24 was easily transformed by further heating into 22 (80%).…”

“…Caled for C8H9N30: C, 58.89; H, 5.56; N, 25.75. Found: C, 58.71; H, 5.56; N, 25.67. 2-Azido-5-methylbenzaldehyde (11). A mixture of 2-azido-5-methylbenzyl alcohol (32) (1.074 g, 6.6 mmol), pyridinium chlorochromate (2.120 g, 9.9 mmol), and dichloromethane (20 mL) was stirred for 1.5 h at room temperature.…”

5-Deazaflavin derivatives as inhibitors of p53 ubiquitination by HDM2

“…Prepared using general method 5.7 from 3a (R 5 = F, R 6,7 = H; 62 mg, 0.28 mmol) and 4 (R 1–3 = H, R 4 = NO 2 , X = OTs; 108 mg, 0.34 mmol). 44,45 Yellow solid (23.0 mg, 23%). Mp: 305–307 °C; IR (KBr): 3.425 (NH), 1.712 (C O), 1.679 (C O), 1.619 (C C), 1.487 (NO 2 ), 1.328 (NO 2 ) cm −1 ; 1 H NMR: δ 7.25 (1H, t, J = 7.5 Hz, Ph 5-H), 7.35–7.44 (2H, m, Ph-H), 7.56–7.74 (2H, m, C7-H & Ph-H), 8.17 (1H, d, J = 7.3 Hz, C8-H), 8.50 (1H, d, J = 7.3 Hz, C6-H), 9.19 (1H, s, C5-H), 11.36 (1H, s, N3-H); 13 C NMR: δ 116.72 (CH, d, J = 19.6 Hz), 117.13 (Cq), 124.05 (Cq), 125.11 (CH), 125.21 (Cq), 125.34 (Cq), 125.36 (CH), 130.03 (CH), 132.60 (CH), 133.12 (CH, d, J = 8.0 Hz), 136.17 (CH), 140.85 (Cq), 142.95 (CH), 156.53 (Cq), 158.52 (Cq, d, J = 252.4 Hz), 159.51 (Cq), 161.71 (Cq); anal.…”

Synthesis and Voltage-Clamp Studies of Methyl 1,4-Dihydro-2,6-dimethyl-5-nitro-4-(benzofurazanyl)pyridine-3-carboxylate Racemates and Enantiomers and of Their Benzofuroxanyl Analogues

“…The crude product was partially purified by crystallization (EtOH/H 2 O) to obtain 7 (40%) sufficiently pure to be used for further reaction. Hydrolysis of 7 (17 g) in a boiling mixture of water (100 mL), EtOH (50 mL), and concentrated hydrochloric acid (75 mL) afforded after 45 min the title product: yield 75%; mp 60−61 °C dec (EtOH/water) (lit . mp 60−61 °C).…”