81534-82-9Relevant articles and documents
Synthesis of 2,5-Disubstituted 3,6-Diamino-1,4-benzoquinones
Hegedus, Louis S.,Odle, Roy R.,Winton, Peter M.,Weider, Paul R.
, p. 2607 - 2613 (1982)
A general synthetic approach to a wide variety of 2,5-disubstituted 3,6-diamino-1,4-benzoquinones was developed.Bromanil was diaminated with ammonia, and adjacent NH2 and OH groups were protected as benzoxazoles by treatment with a carboxylic acid chloride followed by a polyphosphate ester cyclization-dehydration.The resulting 2,5-dibromobenzobis(oxazoles) were monolithiated by halogen-metal exchange with n-butyllithium and then reacted with a variety of electrophiles.The remaining bromide was replaced in a similar fashion.Alternatively the second bromide was replaced by reaction with ? allylnickel halide complexes.The benzoxazole protecting group could be hydrolyzed with zinc(II) chloride/HCl-aqueous ethanol under an inert atmostphere.Air oxidation of the resulting hydroquinone under neutral conditions gave the desired 2,5-disubstituted 3,6-diamino-1,4-benzoquinone in good to excellent overall yield.This method was used to synthesize precursors to the basic ring system of the mitomycin antineoplastic antibiotics.Acid hydrolysis of the benzoxazole protecting group under oxidizing conditions resulted in the production of 2,5-disubstituted 3,6-dihydroxy-1,4-benzoquinone.Methylation followed by reaction with ammonia gave the desired diaminoquinone.
Organic compound, electronic component applying the same and electronic device
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, (2021/07/17)
The invention relates to an organic compound, an electronic component applying the same and an electronic device. The organic compound has a heterocyclic ring with a benzoxazole ring core as a parent structure, a benzoxazole series derivative molecule is