83163-75-1Relevant academic research and scientific papers
Photochemical Cyclopropenation of Alkynes with Diazirines as Carbene Precursors in Continuous Flow
Tanbouza, Nour,Carreras, Virginie,Ollevier, Thierry
supporting information, 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.
Alternative one-pot synthesis of (trifluoromethyl)phenyldiazirines from tosyloxime derivatives: Application for new synthesis of optically pure diazirinylphenylalanines for photoaffinity labeling
Wang, Lei,Murai, Yuta,Yoshida, Takuma,Ishida, Akiko,Masuda, Katsuyoshi,Sakihama, Yasuko,Hashidoko, Yasuyuki,Hatanaka, Yasumaru,Hashimoto, Makoto
supporting information, p. 616 - 619 (2015/03/04)
Alternative one-pot synthesis of 3-(trifluoromethyl)-3-phenyldiazirine derivatives from corresponding tosyloximes is developed. The deprotonation of intermediate diaziridine by NH2- is a new approach for construction of diazirine. Moreover, a novel synthesis of optically pure (trifluoromethyl)diazirinylphenylalanine derivatives was attempted involving these methods.
Synthesis of methoxy-substituted diazirinyl phenylalanine - A novel photoreactive aspartame derivative for functional analysis of sweet receptors
Sakurai, Munenori,Masuda, Katsuyoshi,Wang, Lei,Murai, Yuta,Sakihama, Yasuko,Hashidoko, Yasuyuki,Hatanaka, Yasumaru,Hashimoto, Makoto
, p. 629 - 637 (2016/10/30)
Photoreactive phenylalanine derivatives are well known as functional analysis reagents for target biomolecules. The photophores are commonly introduced at 4-position on benzene. Aspartame, which consists of dipeptide L-Asp-L-Phe-OMe, is one of the most ut
Photoactivation of (p-methoxyphenyl)(trifluoromethyl)diazirine in the presence of phenolic reaction partners
Raimer, Bj?rn,Lindel, Thomas
supporting information, p. 6551 - 6555 (2013/06/27)
Shine light on your chemistry! Irradiating 3-(4-methoxyphenyl)-3- (trifluoromethyl)-3H-diazirine in the presence of equimolar solutions of phenol and tyrosine derivatives leads to Friedel-Crafts alkylations (see scheme), which suggests a strategy for the development of "cleaner" diazirines for chemical biology. Copyright
A photoreactive probe that differentiates the binding sites of noncompetitive GABA receptor antagonists
Shimotahira, Hiroshi,Fusazaki, Sayaka,Ikeda, Izumi,Ozoe, Yoshihisa
supporting information; experimental part, p. 1598 - 1600 (2011/05/11)
γ-Aminobutyric acid (GABA) receptors are postsynaptic membrane protein complexes that are important not only in the regulation of the nervous system but also as targets of drugs and insecticides. We synthesized a photoreactive straight-chain noncompetitiv
A Novel Family of Aromatic Diazirines for Photoaffinity Labeling
Hatanaka, Yasumaru,Hashimoto, Makoto,Kurihara, Hiroko,Nakayama, Hitoshi,Kanaoka, Yuichi
, p. 383 - 387 (2007/10/02)
A series of simple methods for modifying diazirines bearing an aromatic ring has been accomplished.This first versatile approach involving direct substitution on the aromatic ring of diazirines has been achieved by means of the aromatic thallation of (alkoxyphenyl)diazirines.Introduction of the thallium moiety was successfully followed by nitration, iodination, or palladium-catalyzed carbonylation to give a family of substituted aryldiazirines useful for photolabeling.For instance, diazirines labeled with a nitro group can be detected by spectrophotometric methods, and those labeled with an iodo group can be useful in tracer experiments.The (methoxyphenyl)diazirines were also found to be stable under certain demethylation conditions, thus providing a potential source of diazirines with modifiable phenol hydroxyl groups.By means of this approach, a spacer arm to link diazirines with ligands was readily introduced.Radioactive diazirines labeled with carbon-14 or tritium were also prepared using this method.All the new diazirines were derived from a pair of simple (methoxyphenyl)diazirines.The ease of derivatization of the (alkoxyphenyl)diazirines described here may offer a practical approach to simplify the time-consuming methods currently used for diazirine synthesis.
