53872-17-6Relevant academic research and scientific papers
An Efficient Synthesis of Functionalized 2 H -1,3,5-Oxadiazines via Metal-Carbenoid-Induced 1,2,4-Oxadiazole Ring Cleavage
Strelnikova, Julia O.,Rostovskii, Nikolai V.,Khoroshilova, Olesya V.,Khlebnikov, Alexander F.,Novikov, Mikhail S.
, p. 348 - 358 (2020/10/19)
A high-yielding method for the synthesis of 2 H -1,3,5-oxadiazines by rhodium(II)- or copper(II)-catalyzed reaction of 1,2,4-oxadiazoles with α-diazo esters has been developed. The reaction proceeds via attack of the metallocarbenoid on the oxadiazole N2 atom followed by ring opening/1,6-electrocyclization and enables the introduction of alkyl, aryl, oxy, and amino substituents into the 6-position and electron-withdrawing groups into the 2-position of 1,3,5-oxadiazine. The N2-attack and the N4-attack of the carbenoid cause different oxadiazole ring openings, which are controlled by the substitution at C5. The presence of a substituent at this position is a prerequisite for the N2-attack to occur, leading to the formation of 1,3,5-oxadiazines.
Rhodium-catalyzed heterocycloaddition route to 1,3-oxazoles as building blocks in natural products synthesis
Connell,Tebbe,Gangloff,Helquist,Akermark
, p. 5445 - 5459 (2007/10/02)
Rhodium(II) acetate serves as a catalyst for the heterocycloaddition reaction of diazodicarbonyl compounds with nitriles to give functionalized 1,3-oxazole derivatives in a simple one-step procedure. In particular, dimethyl diazomalonate undergoes this re
Functionalized Oxazoles from Rhodium-Catalyzed Reaction of Dimethyl Diazomalonate with Nitriles
Connell, Richard,Scavo, Frank,Helquist, Paul,Akermark, Bjoern
, p. 5559 - 5562 (2007/10/02)
Rhodium(II) acetate catalyzes the reaction of dimethyl diazomalonate with nitriles to give 4-carbomethoxy-5-methoxy-1,3-oxazoles.Oxazole formation exceeds cyclopropane formation even in cases of conjugated and non-conjugated unsaturated nitriles.
