e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis of 2, 5-disubstituted 3, 6-diamino-1, 4-benzoquinones

…, RR Odle, PM Winton, PR Weider

Index: Hegedus, Louis S.; Odle, Roy R.; Winton, Peter M.; Weider, Paul R. Journal of Organic Chemistry, 1982 , vol. 47, # 13 p. 2607 - 2613

Full Text: HTML

Citation Number: 38

Abstract

A general synthetic approach to a wide variety of 2, 5-disubstituted 3, 6-diamino-l, 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- ...

6-allyl-2,4-dimethoxy-3-methyl-1,4-benzoquinone Structure

6-allyl-2,4-dim...

~41%

2,5-diamino-3-methyl-6-prop-2-enylcyclohexa-2,5-diene-1,4-dione Structure

2,5-diamino-3-m...

2,3,5,6-Tetrabromo-1,4-benzoquinone Structure

2,3,5,6-Tetrabr...

~%

2,5-diamino-3-methyl-6-prop-2-enylcyclohexa-2,5-diene-1,4-dione Structure

2,5-diamino-3-m...

3,6-diamino-2,5-dibromo-1,4-hydroquinone Structure

3,6-diamino-2,5...

~%

2,5-diamino-3-methyl-6-prop-2-enylcyclohexa-2,5-diene-1,4-dione Structure

2,5-diamino-3-m...

allylmethylbenzobis(ethyloxazole) Structure

allylmethylbenz...

~%

2,5-diamino-3-methyl-6-prop-2-enylcyclohexa-2,5-diene-1,4-dione Structure

2,5-diamino-3-m...

4-bromo-2,6-diethyl-8-methyl-[1,3]oxazolo[5,4-f][1,3]benzoxazole Structure

4-bromo-2,6-die...

~%

2,5-diamino-3-methyl-6-prop-2-enylcyclohexa-2,5-diene-1,4-dione Structure

2,5-diamino-3-m...

4,8-dibromo-2,6-diethyl-[1,3]oxazolo[5,4-f][1,3]benzoxazole Structure

4,8-dibromo-2,6...

~%

2,5-diamino-3-methyl-6-prop-2-enylcyclohexa-2,5-diene-1,4-dione Structure

2,5-diamino-3-m...

N-[2,5-dibromo-3,6-dihydroxy-4-(propanoylamino)phenyl]propanamide Structure

N-[2,5-dibromo-...

~%

2,5-diamino-3-methyl-6-prop-2-enylcyclohexa-2,5-diene-1,4-dione Structure

2,5-diamino-3-m...

6-allyl-2,4-dihydroxy-3-methyl-1,4-benzoquinone Structure

6-allyl-2,4-dih...

~%

2,5-diamino-3-methyl-6-prop-2-enylcyclohexa-2,5-diene-1,4-dione Structure

2,5-diamino-3-m...

Propanoyl chloride Structure

Propanoyl chloride

3,6-diamino-2,5-dibromo-1,4-hydroquinone Structure

3,6-diamino-2,5...

~76%

N-[2,5-dibromo-3,6-dihydroxy-4-(propanoylamino)phenyl]propanamide Structure

N-[2,5-dibromo-...

2,3,5,6-Tetrabromo-1,4-benzoquinone Structure

2,3,5,6-Tetrabr...

~%

N-[2,5-dibromo-3,6-dihydroxy-4-(propanoylamino)phenyl]propanamide Structure

N-[2,5-dibromo-...

2,3,5,6-Tetrabromo-1,4-benzoquinone Structure

2,3,5,6-Tetrabr...

~%

4-bromo-2,6-diethyl-8-methyl-[1,3]oxazolo[5,4-f][1,3]benzoxazole Structure

4-bromo-2,6-die...

3,6-diamino-2,5-dibromo-1,4-hydroquinone Structure

3,6-diamino-2,5...

~%

4-bromo-2,6-diethyl-8-methyl-[1,3]oxazolo[5,4-f][1,3]benzoxazole Structure

4-bromo-2,6-die...

N-[2,5-dibromo-3,6-dihydroxy-4-(propanoylamino)phenyl]propanamide Structure

N-[2,5-dibromo-...

~%

4-bromo-2,6-diethyl-8-methyl-[1,3]oxazolo[5,4-f][1,3]benzoxazole Structure

4-bromo-2,6-die...

4,8-dibromo-2,6-diethyl-[1,3]oxazolo[5,4-f][1,3]benzoxazole Structure

4,8-dibromo-2,6...

methyl iodide Structure

~%

4-bromo-2,6-diethyl-8-methyl-[1,3]oxazolo[5,4-f][1,3]benzoxazole Structure

4-bromo-2,6-die...

N-[2,5-dibromo-3,6-dihydroxy-4-(propanoylamino)phenyl]propanamide Structure

N-[2,5-dibromo-...

~74%

4,8-dibromo-2,6-diethyl-[1,3]oxazolo[5,4-f][1,3]benzoxazole Structure

4,8-dibromo-2,6...

3,6-diamino-2,5-dibromo-1,4-hydroquinone Structure

3,6-diamino-2,5...

N/A Structure

~10%

4,8-dibromo-2,6-diethyl-[1,3]oxazolo[5,4-f][1,3]benzoxazole Structure

4,8-dibromo-2,6...

2,3,5,6-Tetrabromo-1,4-benzoquinone Structure

2,3,5,6-Tetrabr...

~%

4,8-dibromo-2,6-diethyl-[1,3]oxazolo[5,4-f][1,3]benzoxazole Structure

4,8-dibromo-2,6...

3,6-diamino-2,5-dibromo-1,4-hydroquinone Structure

3,6-diamino-2,5...

~%

4,8-dibromo-2,6-diethyl-[1,3]oxazolo[5,4-f][1,3]benzoxazole Structure

4,8-dibromo-2,6...