952142-99-3Relevant academic research and scientific papers
Photochemical Cyclopropenation of Alkynes with Diazirines as Carbene Precursors in Continuous Flow
Tanbouza, Nour,Carreras, Virginie,Ollevier, Thierry
, p. 5420 - 5424 (2021/07/26)
An efficient synthesis of 3-trifluoromethyl-3-aryl-cyclopropenes via the cyclopropenation reaction of alkynes with photolytically generated carbenes from diazirine compounds is described. This reaction is performed in continuous flow using readily available LEDs under mild reaction conditions. This new and efficient method describes the synthesis of 25 examples of 3-trifluoromethyl-3-aryl-cyclopropenes with yields up to 97%, achieved in continuous flow with a 5 min residence time. Control experiments highlighted that diazirines are more efficient than diazo compounds for this transformation.
Synthesis of diaziridines and diazirines via resin-bound sulfonyl oximes
Protasova, Irina,Bulat, Bekir,Jung, Nicole,Br?se, Stefan
supporting information, p. 34 - 37 (2017/11/28)
Diazirines are one of the most prominent functionalities in labeling experiments in vivo and in vitro because they allow photochemical generation of carbenes. The strategy presented herein describes the formation of diaziridines, being essential precursors in diazirine syntheses, using solid-supported procedures with immobilized sulfonyl oximes. The solid-supported building blocks have been shown to be valuable intermediates for CuAAC and amidation reactions, offering the possibility to build complex compounds with diverse functionalities.
Convenient synthesis of a [1-14C]diazirinylbenzoic acid as a photoaffinity label for binding studies of V-ATPase inhibitors
Bender, Tobias,Huss, Markus,Wieczorek, Helmut,Grond, Stephanie,Von Zezschwitz, Paultheo
, p. 3870 - 3878 (2008/02/13)
Diazirine-tagged systems are considered reliable compounds for photoaffinity labeling (PAL) in biochemical studies as they enable investigation and understanding of biological mechanisms through covalent bonding to the target and subsequent detection. 14C-labeled 4-(3-trifluoromethyl-3H- diazirin-3-yl)benzoic acid (11) was prepared by a lithium-bromide exchange on the bis-silylated 4-bromophenyldiaziridine 19 with subsequent transformations with electrophiles as key steps of the synthesis. Using 14CO 2, which was generated from rather inexpensive Ba14CO 3, the desired diaziridinylbenzoic acid 21 was obtained in 78% yield based on the employed radioactive material. Oxidation under mild conditions then yielded diazirine 11 in a 100 mg scale. This versatile photoaffinity label was selectively attached to the tetrahydropyrane ring of bafilomycin A1 (2) and concanamycin A-derived 3, which both specifically inhibit the V-ATPases. Inhibition assays were performed and revealed that the inhibitory capacities of the labeled derivatives are suitable for PAL studies on this important group of enzymes to elucidate the as yet unknown binding sites. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
