Modified coumarins. 23. Synthesis and structure of cyclohexyldihydroxanthyletin derivatives

Garazd, Ya. L.; Garazd, M. M.; Turov, V. A.; Khilya, V. P.

doi:10.1007/s10600-006-0245-9

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2013

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“…The resulting product decomposed on silica gel and it was purified by basic washing and extensive digestion with methanol to give the imino coumarin OMe-icBA with 3 % yield. In contrast, the oximocoumarin OMe-ocBA was easily prepared in 70 % yield from condensing hydroxylamine chlorhydrate in the presence of sodium acetate [63,67] onto OMe-tcBA.…”

Section: Design and Synthesesmentioning

confidence: 99%

Coumarinylmethyl Caging Groups with Redshifted Absorption

Fournier

Aujard

Saux

et al. 2013

Chemistry A European J

118

145

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The small and synthetically easily accessible coumarinylmethyl backbone has been modified to generate a family of photolabile protecting groups with redshifted absorption. We relied on introducing electron‐donating groups in the 7 position and electron‐withdrawing groups in the 2‐, and 2‐ and 3 positions. In particular, we showed that the diethylamino‐thiocoumarylmethyl and the diethylamino‐coumarylidenemalononitrilemethyl are relevant for uncaging with cyan light. They both exhibit a significant action cross section for uncaging in the 470–500 nm wavelength range and a low light absorption between 350 and 400 nm. These attractive features are favorable to perform chromatic orthogonal photoactivation with UV and blue‐cyan light sources, respectively.

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Section: Design and Synthesesmentioning

confidence: 99%