Synthesis of 2-oxy-3-(pyridinium-1'-yl)-l,4-naphthoquinone derivatives by iodine or hydrogen peroxide oxidation of 1,4-naphthoquinones in the presence of substituted pyridines

Synthesis

Volumn , Issue 6, 1997, Pages 614-616

  Citterio, Attilio ^a   Fochi, Mariacristina ^a   Maronati, Antonietta ^a   Sebastiano, Roberto ^a   Mele, Andrea ^a  

^a POLITECNICO DI MILANO   (Italy)

Author keywords

1,4 naphthoquinone betain; Hydrogen peroxide; Oxidation; Pyridinium salt

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; HYDROGEN PEROXIDE; IODINE; PYRIDINE DERIVATIVE;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0030812011     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1389     Document Type: Article

References (14)

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2. Schonberg, A. S.; Ismail, A. F. A. J. Chem. Soc. 1940, 1374. Ullmann, F.; Ettisch, M. Ber. Dtsch. Chem. Ges. 1921, 62, 529.
3. Weiss, R.; Solomon, N. J.; Meiss, G. E.; Roth, R. Angew. Chem. 1986, 98, 925; Angew. Chem. Int. Ed. Engl. 1986, 25, 917.
4. Weiss, R.; Solomon, N. J.; Meiss, G. E.; Roth, R. Angew. Chem. 1986, 98, 925; Angew. Chem. Int. Ed. Engl. 1986, 25, 917.
5. Bock, H.; Nick, S.; Bats, J. W. Tetrahedron Lett. 1992, 33, 5941.
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7. 2O, 35% MeOH; flow rate: 1 mL/min, detector: Z = 254 nm.
8. Finkley, K. T. In The Chemistry of Quinonoid Compounds; Patai, S. Ed.; Wiley: London, 1988, Part 2, p 684.
9. An exception is the pyridinium anthraquinone reported in Ref. 3. The formation of pyridinium hydroquinone was reported in the reaction of pyridines with 1,4-benzoquinone in the presence of hexachlorocyclotriphosphazatriene: Kiro, Z. B.; Stepanov, B. I. Tr. Mosk. Khim. Teknol. Inst. 1970, 66, 154; Chem. Abstr. 1971, 75, 88452.
10. An exception is the pyridinium anthraquinone reported in Ref. 3. The formation of pyridinium hydroquinone was reported in the reaction of pyridines with 1,4-benzoquinone in the presence of hexachlorocyclotriphosphazatriene: Kiro, Z. B.; Stepanov, B. I. Tr. Mosk. Khim. Teknol. Inst. 1970, 66, 154; Chem. Abstr. 1971, 75, 88452.
11. Similar sensitivity to steric effects was reported in the α-iodination of α-enones by iodine in pyridine: Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayke, C. B. W.; Worulick, P. M.; Urkokovic, M. R. Tetrahedron Lett. 1992, 33, 917. Bovonsombat, P.; Angara, G. J.; Mc Nelis, E. Tetrahedron Lett. 1994, 35, 6787.
12. Similar sensitivity to steric effects was reported in the α-iodination of α-enones by iodine in pyridine: Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayke, C. B. W.; Worulick, P. M.; Urkokovic, M. R. Tetrahedron Lett. 1992, 33, 917. Bovonsombat, P.; Angara, G. J.; Mc Nelis, E. Tetrahedron Lett. 1994, 35, 6787.
13. Williams, D. H.; Ronayne, J.; Moore, H. W.; Shelden, H. R. J. Org. Chem. 1968, 33, 998.
14. Helder, R.; Hummelen, J. C.; Loane, R. W. P. M.; Wiering, J. S.; Wynberg, H. Tetrahedron Lett. 1976, 1831.