Improved Preparation of 6,13-Dichlorotriaryldioxazines using (Diacetoxyiodo)benzene

Abstract

6,13-Dichlorotriaryldioxazines (DClTADO) 1 have been synthesized from 2,5-bis(arylamino)-3,6-dichloro-1,4-benzoquinones (BADClBQ) 2 by oxidation with (diacetoxyiodo)benzene (DIB) under mild conditions in good yields.

References

1. A. H. M. Renfrews, Rev. Prog. Color Relat. Top., 1985, 15, 15.
2. S. L. Chen, Z. H. Zhu and K. C. Chen, Opt. Commun., 1989, 74, 84.
3. K. W. Bortz, B. L. Justus and G. W. Scott, J. Phys. Chem., 1983, 87, 2578.
4. R. C. Harris and G. C. Newland, Brit. Pat., 1 034 181, 1966.
5. R. L. Mital and S. K. Jain, J. Chem. Soc. C, 1971, 1875.
6. K. Kitahara and H. Nishi, Nippon Kagaku Kaishi, 1984, 1870.
7. J. Horst, L. Klaus and H. K. Josef, DE, 3 439 755, 1985.
8. H. Walter and H. Reinhard, EP, 292 906, 1988.
9. S. J. Walter and H. Wolfgang, DE, 3720477, 1988.
10. H. Hahn and R. Blattner, EP, 298 916, 1988.
11. P. J. Stang, Angew. Chem., Int. Ed. Engl., 1992, 31, 274; R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; M. Ochiai, Rev. Heteroatom. Chem., 1989, 292; P. J. Stang, Chem. Rev., 1996, 96, 1123; T. Kitamura and Y. Fujiwara, Org. Prep. Proc. Int., 1997, 4, 409.
12. L. W. Deady and N. H. Quazi, Aust. J. Chem., 1993, 46, 411; R. M. Moriarty, B. A. Berglund and M. S. C. Rao, Synthesis, 1993, 318; D. H. R. Barton, J. C. Jaszberenyi and T. Sinada, Tetrahedron, 1993, 45, 7191; G. C. Reddy, Tetrahedron Lett., 1995, 36, 1001; D. Kumar, O. Prakash and S. P. Singh, J. Chem. Res. (S), 1993, 204.
13. R. Y. Yang and L. X. Dai, J. Org. Chem., 1993, 58, 3381.
14. H. Nishi and M. Murayama, Nippon Kakaku Kaishi, 1979, 432.
15. S. K. Jain, K. G. Ojha and R. R. Gupta, Indian J. Chem., Sect. B, 1979, 17, 278.
16. H. Nishi, M. Kabo and S. Tokita, Nipon Kagaku Kaishi, 1977, 588.