Highly efficient photochemical generation of o-Quinone methide from Mannich bases of phenol derivatives

Tetrahedron Letters

Volumn 38, Issue 28, 1997, Pages 5005-5008

  Nakatani, Kazuhiko ^a   Higashida, Nobuhiro ^a   Saito, Isao ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; MANNICH BASE; PHENOL DERIVATIVE; QUINONE DERIVATIVE; SOLVENT;

AQUEOUS SOLUTION; ARTICLE; DNA CROSS LINKING; PH; PHOTOACTIVATION; PHOTOCHEMISTRY; SYNTHESIS; ULTRAVIOLET IRRADIATION;

EID: 0030752024     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01071-X     Document Type: Article

References (12)

1. For a review, see: Boger, D. L.; Weinreb, S. N. in Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: New York, NY, 1987, pp. 167-213.
2. For a review, see: Tomasz, M. in Advances in DNA Sequence Specific Agents; Hurley, L. H. Ed.; JAI Press; Greenwich, CT, 1992, Vol 1, pp. 247-261.
3. (a) Diao, L.; Yang, C.; Wan, P. J. Am. Chem. Soc. 1995, 117, 5369-5370.
4. (b) Wan, P.; Barker, B.; Diao, L.; Fischer, M.; Shi, Y. Can. J. Chem. 1996, 74, 465-475.
5. (a) Saito, I.; Takayama, M.; Sakurai, T. J. Am. Chem. Soc. 1994, 116, 2653-2654.
6. (b) Nakatani, K.; Shirai, J.; Tamaki, R.; Saito, I. Tetrahedron Lett. 1995, 36, 5363-5366.
7. DNA crosslinking by photochemically and non-photochemically generated quinone methides has been reported, (a) Chatterjee, M.; Rokita, S. E. J. Am. Chem. Soc. 1990, 112, 6397-6397.
8. (b) Chatterjee, M.; Rokita, S. E. J. Am. Chem. Soc. 1994, 116, 1690-1697.
9. (c) Zeng, Q.; Rokita, S. E. J. Org. Chem. 1996, 61, 9080-9081.
10. In the case of 4-phenylphenol, neither spectra broadening nor hypochromic shift was observed by increasing water content in acetonitrile.
11. +) 354.1832, found 354.1847.
12. Cleavage of supercoiled pBR322 DNA by 1 under photoillumination at 312 nm in sodium cacodylate buffer (pH 7.0) at 0 °C was enhanced by heating (37 °C, 1 h) the photolysate, suggesting that DNA alkylation by QM may be actually involved in the photocleavage.