Related Products of 33143-29-2,Some common heterocyclic compound, 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, molecular formula is C12H11NO, 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.
Example 4 2,2-Dimethyl-3,4-dihydro-3-(t-butoxycarbonyl)amino-6-cyano-2H-1-benzopyran (E4) A solution of 6-cyano-2,2-dimethyl-2H-1-benzopyran (1.0g) and N,N-dichloro-t-butylurethane (1.1g) in toluene (20 ml) was heated at 50oC for 5 h. The solution was cooled, and solvent removed in vacuo . The residue was dissolved in dioxan (20 ml) at 0oC, a solution of ammonium acetate (2.08g) in water (20 ml) added, and zinc dust (1.76g) added portionwise. The mixture was stirred for 18 h at room temperature, decanted, and diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4) and evaporated in vacuo . The residue was chromatographed on a silica gel column eluted with ethyl acetate:pentane (1:9) to give the title compound as a solid (1.17g, 72%) which recrystallized from 60-80opetrol as needles having m.pt. 141-2oC. 1H n.m.r. (CDCl3) delta 1.32 (s, 3H); 1.38 (s, 3H); 1.45 (s, 9H); 2.70 (dd, J=15, 4, 1H); 3.13 (dd, J=15, 4, 1H); 3.97 (m, 1H); 4.58 (d, J=9, N H); 6.87 (d, J=9, 1H); 7.40 (m, 2H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2-Dimethyl-2H-chromene-6-carbonitrile, its application will become more common.
Reference:
Patent; BEECHAM GROUP PLC; EP375449; (1990); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts