Direct Amination of Naphthazarin, Juglone, and Some Derivatives

References

• Thomson , R. H. 1987 and 1997 . Naturally Occurring Quinones , 3rd and 4th ed. London : Chapman & Hall .
   Google Scholar
• Finley , K. T. 1988 . In The Chemistry of Quinonoid Compounds Edited by: Patai , S. and Rappaport , Z. Vol. 2 , 537 – 717 . New York : Wiley & Sons .
   Google Scholar
• Farina , F. , Molina , M. T. , Noheda , P. and Paredes , M. C. 1992 . Polycyclic hydroxyquinones, 27: Tautomerism in 1,4‐dihydroxy‐9,10‐anthraquinone monoimines—cycloaddition reactions of their 1,4‐anthraquinonoid tautomers . Tetrahedron , 39 : 8437 – 8450 . See for example
   Google Scholar
• Sokolyuk , N. T. and Pisulina , L. P. 1994 . Synthesis and photochemical properties of pyrazolonaphthacenone peri‐phenoxy derivatives . Zh. Org. Khim. , 30 : 795
   Google Scholar
• Popov , S. I. and Volosenko , V. P. 1981 . Zh. Org. Khim. , 17 : 444 – 445 .
   Google Scholar
• Fieser , L. F. and Fieser , M. 1934 . The tautomerism of the aminonaphthoquinones . J. Am. Chem. Soc. , 56 : 1565 – 1578 .
   Google Scholar
• Tagagi , K. , Matsuoka , M. , Kubo , Y. and Kitao , T. 1985 . Quinone‐quinoneimine tautomerism of 5,8‐bis(donor)substituted 1,4‐naphthoquinonoid dyes . J. Soc. Dyers Colour. , 101 : 140 – 143 .
   Google Scholar
• Shirai , K. , Oshida , A. and Matsuoka , M. 1998 . Absorption spectra and tautomerism of aminonaphthazarins . J. Soc. Dyers Colour. , 114 : 56 – 61 .
   Google Scholar
• Weiss , U. , Merlini , L. and Nasini , G. 1987 . Naturally occurring perylenequinones . Prog. Chem. Org. Nat. Prod. , : 1 – 71 .
   Google Scholar
• Arnone , A. , Merlini , L. , Mondelli , R. , Nasini , G. , Ragg , E. , Scaglioni , L. and Weiss , U. 1993 . NMR‐study of tautomerism in natural perylenequinones . J. Chem. Soc. Perkin Trans. 1 , : 1447 – 1454 .
   Google Scholar
• Arnone , A. , Brambilla , U. , Merlini , L. , Nasini , G. and Scaglioni , L. 1995 . Natural perylenequinones—reaction with ammonia . Gazz. Chim. Ital. , 125 : 427 – 430 .
   Google Scholar
• Farina , F. , Peredes , M. C. and Stefani , V. 1988 . Polycyclic hydroxyquinones. part 25: Regioselective Diels—Alder reactions of 5‐amino‐8‐hydroxy‐1,4‐naphthoquinone and derivatives with 1‐methoxy‐ and 1‐(trimethylsilyloxy)‐buta‐1,3‐diene . J. Chem. Res. (M) , : 2073 – 2081 .
   Google Scholar
• Mischenko , N. P. , Fedoreyev , S. A. , Pokhilo , N. D. , Anufriev , V. Ph. , Denisenko , V. A. and Glazunov , V.P. Echinamines . 2005 . A and B, first aminated hydroxynaphthazarins from the sea urchin Scaphechinus mirabilis . J. Nat. Prod. , 68 : 1390 – 1393 .
   PubMed Web of Science ®Google Scholar
• Pokhilo , N. D. , Yakubovskaya , A. Ya. , Denisenko , V. A. and Anufriev , V. Ph. 2006 . Regiospecificity in the reaction of 2,3‐dichloronaphthazarins with azide anions: Synthesis of echinamine A. A metabolite produced by the sea urchin Scaphechinus mirabilis . Tetrahedron Lett. , 47 : 1385 – 1387 .
   Google Scholar
• Farina , F. , Martinez‐Utrilla , M. , Peredes , M. C. and Stefani , V. 1985 . Synthesis of 5‐amino‐8‐hydroxy‐1,4‐naphthoquinone derivatives . Synthesis , : 781 – 784 .
   Google Scholar
• Bittner , S. and Lempert , D. 1994 . Reaction of hydroxylamines with 1,4‐quinones: A new direct synthesis of aminoquinones . Synthesis , : 917 – 919 .
   Google Scholar
• Parker , K. A. and Sworin , M. E. 1981 . Assignment of regiochemistry to substituted naphthoquinones by chemical and spectroscopic method: Amino‐, hydroxy‐, and bromojuglone derivatives . J. Org. Chem. , 46 : 3218 – 3223 .
   Google Scholar
• Smith , T. H. and Wu , H. Y. 1982 . Quinone chemistry: Synthesis of a masked naphthazarin synthon . J. Org. Chem. , 47 : 1974 – 1976 .
   Google Scholar
• Garden , J. F. and Thomson , R. H. 1957 . Quinones, part VI: Some new polyhydroxynaphthaquinones . J. Chem. Soc. , : 2483 – 2489 .
   Google Scholar