75214-03-8Relevant academic research and scientific papers
Boron-Catalyzed Azide Insertion of α-Aryl α-Diazoesters
San, Htet Htet,Wang, Chun-Ying,Zeng, Hai-Peng,Fu, Shi-Tao,Tang, Xiang-Ying,Jiang, Min
, p. 4478 - 4485 (2019/05/01)
A challenging metal-free azide insertion of α-aryl α-diazoesters in the presence of B(C6F5)3 (5 mol %) was developed for the first time. The reaction features an easy operation, wide substrate scope, and mild conditions an
Reductive azidation of carbonyl compounds via tosylhydrazone intermediates using sodium azide
Barluenga, Jose,Tomas-Gamasa, Maria,Valdes, Carlos
supporting information; experimental part, p. 5950 - 5952 (2012/07/03)
Simple and direct: Aldehydes and ketones can be transformed into alkyl azides through a reductive coupling of the corresponding tosylhydrazones in a process that takes place simply in the presence of K2CO3, tetrabutylammonium bromide
Synthesis ofα-azido ketones and esters using recyclable hypervalent iodine reagent
Telvekar, Vikas N.,Patile, Hemlata V.
experimental part, p. 131 - 135 (2011/02/27)
A simple and mild method for the preparation of αazido ketones and esters using hypervalent iodine reagent, 4,4'-bis-(dichloroiodo)-biphenyl, and sodium azide in 1,4-dioxane is discussed. Advantages of this system are easy workup, recyclable reagent, and
A one-pot preparation of 5-oxo 2,4-disubstituted 2,5-dihydro-1 H -imidazol-2-carboxylates from α-bromo esters
Ciez, Dariusz,Svetlik, Jan
body text, p. 315 - 318 (2011/03/23)
Nucleophilic substitution of a bromine atom by the azide group in aryl- and heteroaryl -α- bromoacetates triggers cascade reactions leading to imidazolin-5-ones formation. The α-azidoacetate intermediates undergo a transformation into non-isolable 2-imino
Intermolecular C-H and Si-H insertion reactions with halodiazoacetates
Bonge, Hanne Therese,Hansen, Tore
experimental part, p. 91 - 96 (2009/06/24)
Ethyl halodiazoacetates react with a range of substrates in regioselective rhodium(II)-catalysed C-H and Si-H insertion reactions giving α-halocarbonyl products in up to 82% yield. The halodiazoacetates are a novel class of diazo compounds that can undergo intermolecular carbenoid C-H insertion reactions, thus broadening the synthetic utility of such reactions. Georg Thieme Verlag Stuttgart.
Revisiting nucleophilic substitution reactions: Microwave-assisted synthesis of azides, thiocyanates, and sulfones in an aqueous medium
Ju, Yuhong,Kumar, Dalip,Varma, Rajender S.
, p. 6697 - 6700 (2007/10/03)
A practical, rapid, and efficient microwave (MW) promoted synthesis of various azides, thiocyanates, and sulfones is described in an aqueous medium. This general and expeditious MW-enhanced nucleophilic substitution approach uses easily accessible starting materials such as halides or tosylates in reaction with alkali azides, thiocyanates, or sulfinates in the absence of any phase-transfer catalyst, and a variety of reactive functional groups are tolerated.
Reaction of α-iminomethylene amino esters with mono- and bidentate nucleophiles: A straightforward route to 2-amino-1H-5-imidazolones
Heras, Montserrat,Ventura, Montserrat,Linden, Anthony,Villalgordo, José M.
, p. 4371 - 4388 (2007/10/03)
The reaction between α-iminomethylene amino esters with different mono- and bidentate nucleophiles has been studied. It has been shown that the reactions with primary and secondary amines as monodentate nucleophiles afford 2-aminoimidazolones efficiently under very mild conditions. Judicious selection of the primary amines employed can modulate the regioselectivity. Analogous reactions employing bidentate nucleophiles (e.g. amidines) also afford imidazolyl derivatives. The formation of the latter is preferred over the formation of seven-membered heterocycles of the triazepinone type. The optimized methodology in solution described herein should be readily adaptable to use in the solid phase for the parallel synthesis of collections of 2-aminoimidazolone derivatives with a high degree of molecular diversity.
Reaction of α-Azido Esters with Lithium Ethoxide: Synthesis of Dehydroamino Esters and α-Keto Esters
Manis, Paul A.,Rathke, Michael W.
, p. 4952 - 4954 (2007/10/02)
α-Azido esters 4 react with catalytic amounts of ethoxide in tetrahydrofuran/ethanol to evolve nitrogen and form dehydroamino esters 3.Acid hydrolysis gives α-keto esters 5 in good yields.
