Untitled

Abstract

Photoreactive cross-linking reagents that simultaneously contain a trifluoromethyldiazirine and an o-nitrobenzyl groups were synthesized for the first time. Photochemical properties of the reagents were studied, and the possibility of separate activation of the diazirine group and o-nitrobenzyl linker was shown.

Three‐Membered Heterocycles. Structure and Reactivity

“…Once the carbene intermediates are formed, the reactivity is much the same as for carbenes generated by any other method. For example, when the aryl diazirine 773 is photolyzed in ethanol, the major product (774) results from the insertion of carbene in the OÀH bond of the solvent [756]. Similar behavior is observed in aqueous media (i.e., 775 !…”

“…Alkoxy substituted diazirines can be prepared from alcohols. Thus, norboranol 755 was treated with cyanamide and methanesulfonic acid to afford an intermediate isouronium salt (756) that was oxidized with hypochlorite to give the diazirine 757 [745]. Diazirines have also been prepared by the partial hydrolysis of nitriles, followed by hypochlorite oxidation [746].…”

Fishing for Drug Targets: A Focus on Diazirine Photoaffinity Probe Synthesis

“…Oxidation of a tolyl motif 137 to the benzoic acid 157 with potassium permanganate occurred in excellent yield (95%) when performed at 50 °C over 6 h . The same conditions over 15 h resulted in a significantly lower yield (31%), perhaps owing to destruction of the diazirine ring . In another example of TPDs withstanding strong oxidants, ortho -periodic acid (8 equiv), chromium trioxide (10 mol %), and acetic anhydride were used to perform an oxidative cyclization on 138 (synthesized by chlorosulfonylation of 137 ) via a benzoic acid intermediate to give a low yield (28%) of 158 over the three steps .…”