Highly diastereoselective thermal decomposition of 3-(azidomethylene)dihydrofuran-2-one

The Chemistry of Vinyl, Allenyl, and Ethynyl Azides

“…40 But, a rapid subsequent reaction led to the formation of the dimers 186a -c , which were quickly oxidized to the corresponding aromatic pyrazines in the case of R = H. This dimerization can be catalyzed by traces of moisture. 95 In some cases, the formation of cyano compounds from vinyl azides was 141 Since vinyl azides like 34 are electron -rich olefi ns, [2 + 2] cycloaddition with electrondefi cient alkenes such as diphenylketene could lead to azidocyclobutanes. Even by irradiation of 184d,e at − 80 to − 120 ° C and NMR spectroscopy at the same temperature, it was not possible to detect 2,3 -bridged 2 H -azirines bearing a fi ve -membered ring such as 185d,e .…”

“…and other142,145 cases, however, different interpretations were offered. The 2 -azidobuta -1,3 -dienes 92a,b underwent [4 + 2] cycloaddition in the Scheme 5.24 Formation of cyano compounds from vinyl azides95,141 …”

Milder Preparation of a g-Azido-a-diazo-b-keto Ester by Consecutive Introduction of Azido and Diazo Groups

“…1 Organic azides are valuable intermediates for the synthesis of many nitrogencontaining molecules, 2 including heterocycles and natural products. 3 Although the isoelectronic azido and diazo functionalities are synthetically useful, the chemical behavior of compounds decorated with both azido and diazo groups remains unexplored. 4 Some years ago, we reported 5 the synthesis of γ-azido-α-diazo-β-keto esters and the chemoselective transformation of their multiple functional groups that ultimately gave more elaborated structures.…”

Allylic azides as potential building blocks for the synthesis of nitrogenated compounds

“…Organic azides [1][2][3] are widely used in synthetic preparation of heterocycles and nitrogen-containing compounds commonly related to natural products and pharmacologically active substances. [4][5][6][7][8][9] The reaction of azido compounds with tertiary phosphorus reagents 10,11 affords phosphorus-nitrogen ylides (the Staudinger reaction) 12 which can be further converted to many classes of nitrogenated derivatives such as imines, amines, carboxamides and phosphoramides, usually in good yield and high chemoselectivity. [13][14][15][16][17][18][19] Recently we have reported a straightforward synthesis of γ-azido-α-diazo-β-keto esters 20 and their chemoselective transformations to 2-azido-3-furanones 21 and phosphorylaminodiazo esters 22 under mild conditions and in high yield, illustrating the versatility of multifunctional azido compounds as building blocks through more elaborated structures.…”