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Discovery of Long-Wavelength Photoactivatable Diaryltetrazoles for Bioorthogonal 1,3-Dipolar Cycloaddition Reactions.

  作者 Wang, Yizhong;Hu, Wen J.;Song, Wenjiao;Lim, Reyna K. V.;Lin, Qing;  
  选自 期刊  Organic Letters;  卷期  2008年10-17;  页码  3725-3728  
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[摘要]Compounds (More Than One Hetero Atom)) Section Several long-wavelength (365 nm) photoactivatable diaryltetrazoles I (R1 = 4-MeO2CC6H4; R2 = Ph, 4-H2NC6H4, 2-Me2NC6H4, 2-MeO-4-O2NC6H3, 4-(PhCH:CH)C6H4, etc.) were discovered by screening a series of substituted diaryltetrazoles and subsequently showed excellent reactivity in the photoactivated 1,3-dipolar cycloaddn. reactions toward electron-deficient and conjugated alkenes R3R4C:CH2 (R3 = CN, CO2Me, Ph, PhNHCO, 4-ClC6H4, etc.; R4 = H, Me) or N-methylmaleimide in org. solvents as well as an alkene-contg. protein in the aq. buffer. The corresponding pyrazolines, e.g. II, were obtained as single regioisomers in moderate to excellent yields.

 
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