An Efficient Synthesis of 2,5-Diamino-1,4-benzoquinone

Abstract

A novel and efficient synthesis of 2,5-diamino-1,4-benzoquinone is described. The reaction involves a palladium/charcoal hydrogenolysis as the key step and provides the desired product in only four steps and very good overall yield.

Key words

palladium-on-charcoal - hydrogenolysis - 2,5-diamino-3,6-dibromoquinone - terreusinone

References

• 1 Lee SM. Li X. Jiang H. Cheng JG. Seong S. Choe HD. Whason B. Tetrahedron Lett.  2003,  44:  7707 
• 2a The Merck Index   12th ed:  Merck & Co., Inc.; White House Station, NJ: 1996.  p.1137 
• 2b Cavallito CJ. Soria AE. Hoppe JO. J. Am. Chem. Soc.  1950,  72:  2661 
• 3a Osman AM. Mohamed SA. U. A. R. J. Chem.  1971,  14:  475 ; Chem. Abstr. 1974, 80, 16426f
• 3b Mayalarp SP. Hargreaves RHJ. Butler J. O’Hare CC. Hartley JA. J. Med. Chem.  1996,  39:  531 
• 4 Moore HW. Shelden HR. Shellhamer DF. J. Org. Chem.  1969,  34:  1999 
• 5 Osman AM. J. Am. Chem. Soc.  1957,  79:  966 
• 6a Cason J. Org. React.  1948,  4:  305 
• 6b Niedermeyer THJ. Mikolasch A. Lalk M. J. Org. Chem.  2005,  70:  2002 
• 7 Soliman AM. El-Saghier AM. Synth. Commun.  2001,  31:  2149 
• 8 Qiao GGH. Meutermans W. Wong WW. Traubel M. Wentrup C. J. Am. Chem. Soc.  1996,  118:  3852 
• 9 Kobayashi K. Takenchi H. Seko S. Kanno Y. Kujime S. Suginome H. Helv. Chim. Acta  1993,  76:  2942 
• 10a Vogel’s Textbook of Practical Organic Chemistry   5th ed.:  Longman; New York: 1989.  p.1025 
• 10b Hegedus LS. Odle RR. Winton PM. Weider PR. J. Org. Chem.  1982,  47:  2607 
• 11 King AO. Shinkai I. In Encyclopedia of Reagents for Organic Synthesis   Vol. 6:  Paquette LA. Wiley; New York: 1995.  p.3867 
• 12 Danne S. Ranft J. Paul H. Tetrahedron Lett.  1964,  45:  3355