Novel photo-induced oxidative cyclization of 1,3-dimethyl-5-(1- arylmethylidene)pyrimidine-2,4,6(1,3,5H)-triones: Synthesis and properties of areno[5,6]pyrano[2,3-d]pyrimidine-2,4(1,3H)-dionylium ions and their photo-induced autorecycling oxidizing reaction toward some amines

Tetrahedron

Volumn 61, Issue 21, 2005, Pages 4919-4930

  Naya, Shin Ichi ^a   Miyagawa, Masashi ^a   Nitta, Makoto ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

Benzo 5,6 pyrano 2,3 d pyrimidine 2,4(1,3H) dionylium tetrafluoroborate; Photo induced autorecycling oxidation; Photo induced oxidative cyclization; X ray analysis

Indexed keywords

1,3 DIMETHYLBENZO[5,6]PYRANO[2,3 D]PYRIMIDINE 2,4(1,3H) DIONYLIUM PERCHLORATE; 1,3 DIPHENYLBENZO[5,6]PYRANO[2,3 D]PYRIMIDINE 2,4(1,3H) DIONYLIUM TETRAFLUOROBORATE; 8,10 DIMETHYLNAPHTHO[1',2':5,6]PYRANO[2,3 D]PYRIMIDINE 9,11(8,10H) DIONYLIUM PERCHLORATE; 8,10 DIPHENYLNAPHTHO[1',2':5,6]PYRANO[2,3 D]PYRIMIDINE 9,11(8,10H) DIONYLIUM TETRAFLUOROBORATE; 9,11 DIMETHYLNAPHTHO[1',2':6,5]PYRANO[2,3 D]PYRIMIDINE 8,10(9,11H) DIONYLIUM PERCHLORATE; AMINE; BORIC ACID; KETONE DERIVATIVE; OXIDIZING AGENT; PERCHLORIC ACID; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIZATION; MEASUREMENT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PHOTOCHEMISTRY; PRIORITY JOURNAL; RECYCLING; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 18144371987     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.03.052     Document Type: Article

References (31)

1. F. Muller F. Muller Chemistry and Biochemistry of Flavoenzymes Vol. 1 1991 CRC Boca Raton 1 71 and references cited therein
2. G.A. Hamilton E.T. Kaiser F.J. Kezdy Progress in Bioorganic Chemistry Vol. 1 1971 Wiley New York 83
3. C.C. Chiu, K. Pan, and F. Jordan J. Am. Chem. Soc. 117 1995 7027 7028
4. J. Kim, S.E. Hoegy, and P.S. Mariano J. Am. Chem. Soc. 117 1995 100 105
5. S. Murahashi, S. Ono, and Y. Imada Angew. Chem., Int. Ed. 41 2002 2366 2368
6. K. Bergstad, S. Jonsson, and J. Bächvall J. Am. Chem. Soc. 121 1999 10424 10425
7. K.A. Van Houten, J. Kim, M.A. Bogdan, D.C. Ferri, and P.S. Mariano J. Am. Chem. Soc. 120 1998 5864 5872
8. Y. Zheng, and R.L. Ornstein J. Am. Chem. Soc. 118 1996 9402 9408
9. E.C. Breinlinger, C.J. Keenan, and V.M. Rotello J. Am. Chem. Soc. 120 1998 8606 8609
10. J.J. Hasford, and C.J. Rizzo J. Am. Chem. Soc. 120 1998 2251 2255
11. J. Antony, D.M. Medvedev, and A.A. Stuchebrukhov J. Am. Chem. Soc. 122 2000 1057 1065
12. C. Walsh Acc. Chem. Res. 19 1986 216 221 and references cited therein
13. F. Yoneda, and K. Tanaka Med. Res. Rev. 4 1987 477 506 and references cited therein
14. F. Yoneda, R. Hirayama, and M. Yamashita Chem. Lett. 1980 1157 1160
15. M. Nitta, and Y. Tajima Synthesis 2000 651 654
16. T. Takayasu, Y. Mizuta, and M. Nitta Heterocycles 54 2001 601 606
17. S. Naya, Y. Iida, and M. Nitta Tetrahedron 60 2004 459 467
18. S. Naya, and M. Nitta Tetrahedron 59 2003 3709 3718
19. S. Naya, H. Miyama, K. Yasu, T. Takayasu, and M. Nitta Tetrahedron 59 2003 1811 1821
20. S. Naya, H. Miyama, K. Yasu, T. Takayasu, and M. Nitta Tetrahedron 59 2003 4929 4938
21. S. Naya, and M. Nitta Tetrahedron 59 2003 7291 7299
22. S. Naya, T. Tokunaka, and M. Nitta J. Org. Chem. 68 2003 9317 9321
23. M.A. Miranda, and H. Garcia Chem. Rev. 94 1994 1063 1089
24. R. Akaba, M. Kamata, H. Sakuragi, and K. Tokumaru Tetrahedron Lett. 33 1992 8105 8108
25. R. Akaba, H. Sakuragi, and K. Tokumaru J. Chem. Soc., Perkin Trans. 2 1992 291 297
26. B. Branchi, M. Bietti, G. Ercolani, M.A. Izquierdo, M.A. Miranda, and L. Stella J. Org. Chem. 69 2004 8874 8885
27. M. Sekiya, and C. Yanaihara Chem. Pharm. Bull. 17 1969 747 751
28. S. Akabori Chem. Ber. 66B 1933 139
29. K. Yamane, H. Yamamoto, and M. Nitta J. Org. Chem. 67 2002 8114 8122
30. S. Naya, and M. Nitta Tetrahedron 60 2004 9139 9148
31. A. Altomare, M.C. Burla, M. Camalli, M. Cascarano, C. Giacovazzo, A. Guagliardi, and G. Polidori J. Appl. Crystallogr. 27 1994 435