Sulfuric Acid → 1,2-Naphthoquinone
반응식
[OH:1][C:2]1[C:3](=[O:16])[C:4]2[C:9]([C:10](=O)[C:11]=1CC=C)=[CH:8][CH:7]=[CH:6][CH:5]=2.S(=O)(=O)(O)O>C(O)C>[CH:7]1[CH:8]=[C:9]2[CH:10]=[CH:11][C:2]([C:3](=[O:16])[C:4]2=[CH:5][CH:6]=1)=[O:1]참가 물질
4
실험 절차
The process shown in Scheme 2 can be used for the preparation of compounds in Formula II, III and IV when R7 is not hydrogen and X is oxygen from same starting material 1-1 as shown in Scheme 1. The reaction of 2-hydroxy-1,4-naphthoquinone 1-1 with the appropriate allylbromide gives 2-allyloxy-1,4-naphthoquinone 2-2. Rearrangement of 2-2 in ethanol afford 2-hydroxy-3-allyl-1,4-naphthoquinone 2-3, which can be cyclized by sulfuric acid treatment to form orthonaphthoquinone 2-4. Oxidation of 2-4 with n-bromosuccinimide and lead tetraacetate gives 3-acetoxy-orthonaphthoquinone 2-5. Hydrochloric acid treatment of compound 2-5 gives 2-alkyl (or aryl)-3-alkyl (or aryl)-naphtha[2,3-b]furan-4,9-dione 2-6.