Chemistry of 5,8-Dihydroxy-[1,4]-naphthoquinone, a Key chromophore in aged cellulosics

Mini-Reviews in Organic Chemistry

Volumn 10, Issue 3, 2013, Pages 302-308

  Hosoya, Takashi ^a   French, Alfred D ^b   Rosenau, Thomas ^a  

^a UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

^b SOUTHERN REGIONAL RESEARCH CENTER   (United States)

Author keywords

5,8 Dihydroxy 1,4 naphthoquinone; Alkylation; Cellulose; Chromophores; Cycloaddition; Naphthoquinones; Reduction; Substitution; Yellowing

Indexed keywords

ADDITION REACTIONS; ALKALINITY; CHROMOPHORES; KETONES; OLEFINS; SULFUR COMPOUNDS;

% REDUCTIONS; 5,8-DIHYDROXY-1,4-NAPHTHOQUINONE; CELLULOSIC MATERIAL; CYCLOADDITIONS; ECONOMIC IMPORTANCE; KEY PROCESS; NAPHTHOQUINONES; PULP AND PAPER INDUSTRY; YELLOWING;

CELLULOSE;

EID: 84882766626     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570193X11310030008     Document Type: Review

References (59)

1. Rosenau, T.; Potthast, A.; Milacher, W.; Hofinger, A.; Kosma, P. Isolation and identification of residual chromophores in cellulosic materials. Polymer, 2004, 45, 6437-6443.
2. Rosenau, T.; Potthast, A.; Milacher, W.; Adorjan, I.; Hofinger, A.; Kosma, P. Discoloration of cellulose solutions in N-methyl-morpholine-Noxide (Lyocell). Part 2: Isolation and Identification of Chromophores. Cellulose, 2005, 12, 197-208.
3. Rosenau, T.; Potthast, A.; Kosma, P.; Suess, H.-U.; Nimmerfroh, N. First isolation and identification of residual chromophores from aged bleached pulp samples. Holzforschung, 2007, 61, 656-661.
4. Krainz, K.; Potthast, A.; Suess, U.; Dietz, T.; Nimmerfroh, N.; Rosenau, T. Effects of selected key chromophores on cellulose integrity upon bleaching. Holzforschung, 2009, 63, 647-656.
5. Rosenau, T.; Potthast, A.; Krainz, K.; Yoneda, Y.; Dietz, T.; Shields, Z.P.I.; French, A.D. Chromophores in cellulosics, VI. First isolation and identification of residual chromophores from aged cotton linters. Cellulose, 2011, 18, 1623-1633.
6. Savko, M.; Kaščáková, S.; Mojzeš, P.; Jancura, D.; Miškovský, P.; Uličný, J. Ground and excited state properties of naphthazarin: Absorption spectroscopy and theoretical modeling study. J. Mol. Struc.: THEOMEM, 2007, 803, 79-87.
7. Hosoya, T.; French, A.D.; Rosenau, T. Chemistry of 2,5-dihydroxy-[1,4]-benzoquinone, a key chromophore in aged cellulosics. MiniRev. Org. Chem., in press.
8. Rosenau, T.; Potthast, A.; Kosma, P.; Süss, H.-U.; Nimmerfroh, N. Isolation and identification of residual chromophores from aged bleached pulp samples. Holzforschung, 2007, 61, 656-661.
9. Gompper, R.; Sramek, M. Anthraquinone and napthacene quinone from napthoquinones or 1,4-dihydroxyanthraquinone and 4-dimethylamino-1,1,2-trimethoxybutadiene. Synthesis, 1981, 649-650.
10. Cameron, D.W.; Feutrill, G.I.; McKay, P.G. Regiospecific synthesis of quinizarin and naphthazarin derivatives by cycloaddition. Aust. J. Chem., 1982, 35, 2095-2109.
11. Schmidt, R.R.; Wagner, A. Syntheses and reactions of acylated 4-amino-1-hydroxy-1,3-butadienes. Synthesis, 1982, 958-962.
12. Krohn, K.; Tolkiehn, K.; Lehne, V.; Schmalle, H.W.; Gruetzmacher, H.F. Synthetic anthracyclinones, XXIX. Quinone antibiotics with five substituents at the hydroaromatic ring. Liebigs Annal. Chem., 1985, 1311-1328.
13. Takeuchi, N.; Ohki, J.; Tobinaga, S. Nitrodienamines: an easy synthesis and [4+2] cycloaddition reactions with α, β-unsaturated carbonyl compounds and quinines. Chem. Pharm. Bull., 1988, 36, 481-487.
14. Christopher J.; Gill, M.; Saubern, S. Pigments of fungi. XXI. Synthesis of (±)-6-demethoxyaustrocortirubin Burns. Aust. J. Chem., 1991, 44, 1427-1445.
15. Khan, A.T.; Blessing, B.; Schmidt, R.R. An expedient and efficient synthesis of naturally occurring hydroxy-substituted anthraquinones. Synthesis, 1994, 255-257.
16. Tamura, Y.; Wada, A.; Sasho, M.; Kita, Y. Cycloaddition of homophthalic anhydride: a new and simple route to linearly condensed phenolic compounds. Tetrahedron Lett., 1981, 22, 4283-4286.
17. Tamura, Y.; Sasho, M.; Nakagawa, K.; Tsugoshi, T.; Kita, Y. Strong base induced cycloaddition of homophthalic anhydrides leading to peri-hydroxy polycyclic compounds. J. Org. Chem., 1984, 49, 473-478.
18. Hayakawa, K.; Aso, M.; Kanematsu, K. Site-selective Diels-Alder reactions of 1,4,5,8-naphthodiquinones with anthracenes and successively with cyclopentadiene: electronic effects vs. steric effects. J. Org. Chem., 1985, 50, 2036-2040.
19. Farina, F.; Carmen Paredes, M.; Stefani, V. Polycyclic hydroxyquinones. XXIV. Diels-Alder reactions of 5-amino-8-hydroxy-1,4-naphthoquinone. Novel trans-cycloaddition reactions with derivatives of 1,4-dihydro-1,4-methanoanthracene-9,10-dione. Tetrahedron, 1986, 42, 4309-4318.
20. Grabley, S.; Kluge, H.; Hoppe, H.U. Diels Alder reaction of streptazoline with naphthoquinone. Angew. Chem., 1987, 99, 692-693.
21. deBie, J.F.M.; Peperzak, R.M.; Daenen, M.J.; Scheeren, H.W. A practical and efficient multigram approach to daunomycinone and derivs. Tetrahedron, 1993, 49, 6463-6472.
22. Lanari, D.; Marrocchi, A.; Minuti, L.; Taticchi, A.; Gacs-Baitz, E. Synthesis of some new enantiopure [2.2] paracyclophanes bearing polycyclic aromatic subunits. Tetrahedron Asym., 2002, 13, 1331-1335.
23. Cuellar, M.A.; Salas, C.; Cortes, M.J.; Morello, A.; Maya, J.D.; Preite, M.D. Synthesis and in vitro trypanocide activity of several polycyclic drimane-quinone derivatives. Bioorg. Med. Chem., 2003, 11, 2489-2497.
24. Hayakawa, K.; Aso, M.; Kanematsu, K. Site-selective Diels-Alder reactions of 1,4,5,8-naphthodiquinones with anthracenes and successively with cyclopentadiene: electronic effects vs. steric effects. J. Org. Chem., 1985, 50, 2036-2040.
25. Laduranty, J.; Lepage, L.; Lepage, Y. Trapping of p-dimethoxy-oquinodimethane: syntheses of quinones and an intermediate of daunomycinone. Can. J. Chem., 1980, 58, 1161-1167.
26. Hariri, M.A.; Pautet, F.; Fillion, H. Generation and [4+2] cycloadditions of dimethyl 4,5-bis(bromomethylene)furandioate, a furan analog of o-quinodimethane. Synlett, 1994, 459-460.
27. Hariri, M.A.; Jouve, K.; Pautet, F.; Domard, M.; Fenet, B.; Fillion, H. Generation and Trapping of 4-Methylene-5-(bromomethylene)-4,5-dihydrothiazole with Dienophiles. J. Org. Chem., 1997, 62, 405-410.
28. Jouve, K.; Pautet, F.; Domard, M.; Fillion, H. Generation and Diels-Alder trapping of 4,5-bis(bromomethylene)-4,5-dihydrothiazole. Eur. J. Org. Chem., 1998, 2047-2050.
29. Potts, K.T.; Walsh, E.B.; Bhattacharjee, D. Cycloaddition routes to azaanthraquinone derivatives. 2. Use of azadienes. J. Org. Chem., 1987, 52, 2285-2292.
30. Jouve, K.; Pautet, F.; Domard, M.; Fillion, H. Generation of a thiazoleo-quinodimethane from an imino derivative and its intermolecular Diels-Alder trapping with alkynes or quinines. Chem. Pharm. Bull., 1999, 47, 1064-1067.
31. Tandon, V.K.; Yadav, D.B.; Chaturvedi, A.K.; Shukla, P.K. Synthesis of (1,4)-naphthoquinono-[3,2-c]-1H-pyrazoles and their (1,4)-naphthohydroquinone derivatives as antifungal, antibacterial, and anticancer agents. Bioorg. Med. Chem. Let., 2005, 15, 3288-3291.
32. Matsuoka, M.; Takei, T.; Kitao, T. Selective butylamination of 5,8-dihydroxy-1,4-naphthoquinone promoted by copper salts. Chem. Let., 1979, 627-630.
33. Tandon, V.K.; Vaish, M.; Khanna, J.M.; Anand, N. Synthesis and pharmacological studies of some (1,4)-naphthoquinono[3,2-c]-1H-pyrazoles, 2-substituted amino-1,4-naphthoquinones, and related compounds. Arch. Pharm., 1990, 323, 383-385.
34. Tandon, V.K.; Vaish, M.; Jain, S.; Khan, Z.K. Synthesis and antimicrobial studies of some 2-substituted amino-1,4-naphthoquinones and related compounds. Acta Pharm., 1993, 43, 173-178.
35. Bittner, S.; Lempert, D. Reaction of hydroxylamines with 1,4-quinones: a new direct synthesis of aminoquinones. Synthesis, 1994, 917-919.
36. Kim, J.H.; Matsuoka, M.; Fukunishi, K. Synthesis and solid state absorption spectra of some aminonaphthoquinone dyes. Dyes Pigm., 1996, 31, 263-272.
37. Arnone, A.; Merlini, L.; Nasini, G.; Vajna P.O. Direct amination of naphthazarin, juglone, and some derivatives. Synth. Comm., 2007, 37, 2569-2577.
38. Zhou, J.; Duan, L.; Chen, H.; Ren, X.; Zhang, Z.; Zhou, F.; Liu, J.; Pei, D.; Ding, K. Atovaquone derivatives as potent cytotoxic and apoptosis inducing agents. Bioorg. Med. Chem. Let., 2009, 19, 5091-5094.
39. Tandon, V.K.; Maurya, H.K. "On water": unprecedented nucleophilic substitution and addition reactions with 1,4-quinones in aqueous suspension. Tetrahedron Let., 2009, 50, 5896-5902.
40. Tandon, V.K.; Maurya, H.K.; Verma, M.K.; Kumar, R.; Shukla, P.K. "On water" assisted synthesis and biological evaluation of nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents. Eur. J. Med. Chem., 2010, 45, 2418-2426.
41. Tanoue, Y.; Terada, A.; Taniguchi, H.; Okuma, T.; Kaai, H.; Anan, M.; Kakara, Y.; Doi, M.; Morishita, S. Synthesis of naphthoquinone derivatives. XIII. A novel synthesis of naphthazarin and juglone derivatives by reaction of naphthazarin and juglone with cyclic enol ethers. Bull. Chem. Soc. Jpn, 1993, 66, 3712-3715.
42. Valderrama, J.A.; Benites, J.; Cortes, M.; Pessoa-M., H.; Prina, E.; Fournet, A. Studies on quinones. part 38: synthesis and leishmanicidal activity of sesquiterpene 1,4-quinones. Bioorg. Med. Chem., 2003, 11, 4713-4718.
43. Tandon, V.K.; Singh, R.V.; Yadav, D.B. Synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antiviral, antifungal and anticancer agents. Bioorg. Med. Chem. Let., 2004, 14, 2901-2904.
44. Tandon, V.K.; Chhor, R.B.; Singh, R.V.; Rai, S.; Yadav, D.B. Design, synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antifungal and anticancer agents. Bioorg. Med. Chem. Let., 2004, 14, 1079-1083.
45. Tandon, V.K.; Yadav, D.B.; Singh, R.V.; Vaish, M.; Chaturvedi, A.K.; Shukla, P.K., Synthesis and biological evaluation of novel 1,4-naphthoquinone derivatives as antibacterial and antiviral agents. Bioorg. Med. Chem. Let., 2005, 15, 3463-3466.
46. Greco, G.; Panzella, L.; Pezzella, A.; Napolitano, A.; d'Ischia, M. Reaction of dihydrolipoic acid with juglone and related naphthoquinones: unmasking of a spirocyclic 1,3-dithiane intermediate en route to naphtho[1,4]dithiepines. Tetrahedron, 2010, 66, 3912-3916.
47. Yakubovskaya, A.Y.; Pokhilo, N.D.; Anufriev, V.F.; Anisimov, M.M. Synthesis and antimicrobial and antifungal activities of compounds of the naphthazarin series. Pharm. Chem. J., 2009, 43, 396-398.
48. Tandon, V.K.; Yadav, D.B.; Singh, R.V.; Chaturvedi, A.K.; Shukla, P.K. Synthesis and biological evaluation of novel (L)-α-amino acid methyl ester, heteroalkyl, and aryl substituted 1,4-naphthoquinone derivatives as antifungal and antibacterial agents. Bioorg. Med. Chem. Lett., 2005, 15, 5324-5328.
49. Pokhilo, N.D.; Yakubovskaya, A.Y.; Glazunov, V.P. Chemistry of naphthazarin derivatives: XV. Bromination of naphthazarin and its derivatives. Russ. J. Org. Chem., 2011, 47, 504-509.
50. Paull, K.D.; Zee-Cheng, R.K. Y.; Cheng, C.C. Substituted naphthazarins as potential anticancer agents. J. Med. Chem., 1976, 19, 337-339.
51. Adams, J.H.; Lewis, J.R.; Paul, J.G. Preparation of aryl esters using polyphosphate ester. Synthesis, 1979, 429-430.
52. Smith, T.H.; Wu, H.Y. Quinone chemistry. Synthesis of a masked naphthazarin synthon. J. Org. Chem., 1982, 47, 1974-1976.
53. Terada, A.; Tanoue, Y.; Hatada, A.; Sakamoto, H. Synthesis of naphthoquinone derivatives. II. Synthesis of shikalkin [(±)-shikonin] and related compounds. Bull. Chem. Soc. Jpn., 1987, 60, 205-213.
54. Betts, R.L.; Murphy, S.T.; Johnson, C.R. Enzymatic desymmetrization/ resolution of epoxy diols derived from 1,4-naphthoquinone, 5-hydroxy-1,4-naphthoquinone and 5,8-dihydroxy-1,4-naphthoquinone. Tetrahedron Asymm., 2004, 15, 2853-2860.
55. Mital, A.; Negi, V.S.; Ramachandran, U. Synthesis and biological evaluation of naphthalene-1,4-dione derivatives as potent antimycobacterial agents. Med. Chem., 2008, 4, 492-497.
56. Kelly, T.R.; Fu, Y.; Sieglen, J.T., Jr.; De Silva, H. Synthesis of an Orange anthrathiophene pigment isolated from a Japanese bryozoan. Org. Let., 2000, 2, 2351-2352.
57. Bakola-C., M.N.; Apazidou, K.K.; Stoyanov, S.; Akrivos, P.D. Application of spectroscopic and computational methods in the study of the electronic excitations of partially silylated hydroxyquinones. Spectrochim. Acta, Part A., 2003, 59A, 1017-1024.
58. Xu, D.-F.; Guan, P.-J.; Li, S.-S. A convenient synthesis of 2-formyl-1,4,5,8-tetramethoxynaphthalene. J. Chem. Res., 2006, 779-780.
59. Kawasaki, M.; Matsuda, F.; Terashima, S. Synthetic studies on nogalamycin congeners. II. Chiral synthesis of the CDEF-ring system of nogalamycin. Tetrahedron, 1988, 44, 5713-5725.