7270-63-5,Some common heterocyclic compound, 7270-63-5, name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, molecular formula is C6H6N2O4, 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.
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. 4.2.17. 2,4-Di(phenanthren-9-yl)-6H-furo[2,3-b]pyran-6-one (5p). Reaction of 1 (85 mg, 0.5 mmol) and 9-ethynylphenanthrene (222 mg, 1.1 mmol) under Rh2(OPiv)4 (6 mg, 0.01 mmol) afforded 5p (98 mg, 40%) as a solid: mp 156-158 C; 1H NMR (300 MHz, CDCl3) delta 8.81-8.62 (4H, m), 8.23 (1H, d, J=7.5 Hz), 8.04-7.85 (5H, m), 7.78-7.53 (8H, m), 6.52 (1H, s), 6.42 (1H, s); 13C NMR (75 MHz, CDCl3) delta 159.3, 158.4, 154.2, 147.8, 131.8, 130.7, 130.6, 130.5, 130.5, 130.2, 129.1, 129.0, 128.8, 128.5, 128.4, 128.0, 127.9, 127.5, 127.4, 127.2, 127.1, 126.9, 126.9, 126.8, 126.7, 125.9, 125.3, 124.8, 123.1, 122.9, 122.5, 122.3, 107.5, 106.0, 101.3; IR (KBr) 2923, 1714, 1646, 1533, 1411, 1266, 1166, 1032, 962, 826, 750 cm-1; HRMS m/z (M+) calcd for C35H20O3: 488.1412. Found: 488.1411.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, its application will become more common.
Reference:
Article; Somai Magar, Krishna Bahadur; Lee, Yong Rok; Kim, Sung Hong; Tetrahedron; vol. 69; 44; (2013); p. 9294 – 9302;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics