The high yield and regioselective conversion of an unactivated aziridine to an oxazolidinone using carbon dioxide with ammonium iodide as the catalyst

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

“…A number of catalysts are known in literature to ease the reaction. Some of these involve quaternary ammonium bromide-functionalized polyethylene glycol, 101 zirconyl chloride, 102 alkali metal halide, 103 Lewis basic ionic liquids, 104 protic onium salt, 105 polyethylene glycolfunctionalized phosphonium salts, 106 DBN, 107 polyethylene glycol functionalized ionic liquids, 108 2,2',2''-terpyridine, 109 and mesoporous zirconium phosphonates. 110 A very few selected examples are described in succeeding paragraphs.…”

Carbon dioxide uptake as ammonia and amine carbamates and their efficient conversion into urea and 1,3-disubstituted ureas

“…However, most catalysts can be reused no more than 3-4 times. Carbon dioxide has been also reacted with aziridines and ionic liquids as catalysts, affording oxazolidones, which are valuable intermediates in several organic synthesis [47][48][49][50].…”

Aziridines in Formal [3+2] Cycloadditions: Synthesis of Five‐Membered Heterocycles

“…It was observed that the Scheme 6. The desired pyrrolo [2,3-b]indole 36 was thus obtained in 90 % yield and converted into physostigmine (37) in two steps. use of chlorotrimethylsilane in combination with Sc(OTf) 3 resulted in a significant enhancement of the yield.…”

“…In this regard, the use of a variety of catalysts such as alkali metal halides, [33][34][35][36][37][38] tetraalkylammonium halide systems, [34] DBN, [37] phenol/DMAP, [39] iodine, [40][41][42] naturally occurring amino acids, [43] (salen)-Cr III /DMAP, [44] zirconyl chloride, [45] quaternary-ammonium-functionalized polyethylene glycol, [46] polystyrenesupported amino acids, [47] polyethylene-glycol-functionalized phosphonium salts, [48] and ionic liquids (ILs) [49,50] has been reported. During the last decade the development of highly efficient methods for chemical fixation of CO 2 and its efficient utilization as a C1 building block has been attracting great interest in organic synthesis and in the chemical industry.…”

“…[34] The lithium-halide-catalysed reaction of aziridine 121 with CS 2 gave the target five-membered cyclic dithiourethane 123 regioselectively. [33,37] The regioselectivities of the lithium-iodide-mediated reactions between aziridines 127 and CO 2 were heavily dependent on the substituents on the aziridines. [34] 2-Aryl-N-tosylaziridines 121 were found to react with carbon dioxide under lithium bromide catalysis conditions at 100°C under atmospheric pressure to give the substituted oxazolidinones 126 in good yield (Scheme 30, b).…”