These common heterocyclic compound, 7270-63-5, name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Computed Properties of C6H6N2O4
General procedure: To a solution of diazo compound 1 (0.5 mmol) and alkynes (1.1 mmol) in toluene (2 mL) was added rhodium(II) pivalate (0.01 mmol). The reaction mixture was stirred at 60C for 0.5-5 h. The solvent was evaporated in rotary evaporator under reduced pressure to give the residue. The residue was purified by flash column chromatography on silica gel to give the product. 4.2.1. 2,4-Diphenyl-6H-furo[2,3-b]pyran-6-one (4). Reaction of 1 (85 mg, 0.5 mmol) and phenylacetylene (112 mg, 1.1 mmol) under Rh2(OPiv)4 (6 mg, 0.01 mmol) afforded 4 (86 mg, 60%) as a solid: mp 88-90 C; 1H NMR (300 MHz, CDCl3) delta 7.64-7.62 (4H, m), 7.55-7.52 (3H, m), 7.39 (2H, t, J=7.5 Hz), 7.30 (1H, d, J=7.5 Hz), 6.87 (1H, s), 6.21 (1H, s); 13C NMR (75 MHz, CDCl3) delta 159.6, 159.1, 154.0, 148.7, 135.3, 131.0, 129.4, 129.1, 128.5, 127.7, 123.7, 105.0, 101.0, 99.9; IR (KBr) 1724, 1607, 1526, 1379, 1295, 1195, 826, 761, 687 cm-1; HRMS m/z (M+) calcd for C19H12O3: 288.0786. Foud: 288.0790.
The synthetic route of 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione has been constantly updated, and we look forward to future research findings.
Reference:
Article; Somai Magar, Krishna Bahadur; Lee, Yong Rok; Kim, Sung Hong; Tetrahedron; vol. 69; 44; (2013); p. 9294 – 9302;,
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