Sterically shielded tetrazoles for a fluorogenic photoclick reaction: tuning cycloaddition rate and product fluorescence
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چکیده
منابع مشابه
Synthesis and reduction kinetics of sterically shielded pyrrolidine nitroxides.
A series of sterically shielded pyrrolidine nitroxides were synthesized, and their reduction by ascorbate (vitamin C) indicate that nitroxide 3, a tetraethyl derivative of 3-carboxy-PROXYL, is reduced at the slowest rate among known nitroxides, i.e., at a 60-fold slower rate than that for 3-carboxy-PROXYL.
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The cycloaddition of pyridinium ylides with alkynes was investigated under mild conditions. A series of 13 pyridinium salts was prepared by alkylation of 4-substituted pyridines. Their reactivity with propiolic ester or amide in various reaction conditions (different temperatures, solvents, added bases) was studied, and 11 indolizines, with three points of structural variation, were, thus, isol...
متن کاملDesign of oligothiophene-based tetrazoles for laser-triggered photoclick chemistry in living cells.
A 405 nm light-activatable terthiophene-based tetrazole was designed that reacts with a fumarate dipolarophile with the second-order rate constant k2 exceeding 10(3) M(-1) s(-1). The utility of this laser-activatable tetrazole in imaging microtubules in a spatiotemporally controlled manner in live cells was demonstrated.
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The development of fluorogenic reactions which lead to the formation of fluorescent products from two nonfluorescent starting materials is highly desirable, but challenging. Reported herein is a new concept of fluorescent product formation upon the inverse electron-demand Diels-Alder reaction of 1,2,4,5-tetrazines with particular trans-cyclooctene (TCO) isomers. In sharp contrast to known fluor...
متن کاملPREPARATION OF (CHLOROCARBONYL) PHENYLKETENB AND ITS CYCLOADDITION REACTION WITH BENZALDEHYDEV
Meldrum's acid, 2'5-diphenyl-1'3-dioxane-4'6-dione, was produced by [2+2] cycloadditions of the (chlorocarbony1)phenylketene with benzaldehyde. Acid hydrolysis of the meldrum's acid regenerated benzaldehyde and also yielded phenylacetic acid as the final product
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ژورنال
عنوان ژورنال: Organic & Biomolecular Chemistry
سال: 2018
ISSN: 1477-0520,1477-0539
DOI: 10.1039/c8ob01404c