Oxygen → 2-Allyloxy-1,4-naphthoquinone
Reaction equation
[H][H].O=O.[OH:5][C:6]1[C:7](=[O:17])[C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2.[CH2:18](Br)[CH:19]=[CH2:20]>>[CH2:20]([O:5][C:6]1[C:7](=[O:17])[C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:19]=[CH2:18]Participants
5
Procedure
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.
Sources & evidence
- ORD record
- ord-e5ff15acb2424e56b96c497d30986f21
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877803B2
Reaction notes
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