Synthesis of Ionic Liquid-Supported Sulfonyl Azide and Its Application in Diazotransfer Reaction

Abstract

The paper describes synthesis of a novel ionic liquid-supported sulfonyl azide and its applications as diazotransfer reagent of active methylene compounds as well as deformylative diazo transfer reagent. The diazo compounds were isolated in excellent yields (82-94%) and high purity. The method offers better separation of product and reagent. This method is experimentally simple and mild, and requires very short reaction time.

Heterocycles-Based Ionic Liquid-Supported Synthesis of Small Organic Molecules

“…The synthesis of IL-anchored azide compounds was achieved by the reaction sequences shown in Scheme 9 [39]. The synthesis of IL-anchored azide compounds was achieved by the reaction sequences shown in Scheme 9 [39].…”

Advances in Functionalized Ionic Liquids as Reagents and Scavengers in Organic Synthesis

“…Wider utility of sulfonyl azides in organic synthesis and problems associated with their safety and purification of the product, encouraged us to synthesize a new ionic liquid-supported sulfonyl azide 155. 112 Synthesis of 155 was achieved as shown in Scheme 45. Initially, the reaction of 1-methylimidazole 14 with 1,3-propanesultone 152 at 0 °C followed by acidification with trifluoromethanesulfonic acid (TfOH) at room temperature gave 153.…”

“…The scope of reagent 155 as a diazotransfer reagent was evaluated by treating it with various active methylene compounds like 1,3-diketones, β-ketoester, and 1,3-diesters 156 (Scheme 46). 112 Reagent 155 afforded diazo compounds 157 in excellent yields with high purity under solvent free conditions in a short period. β-Ketosulfones that have been previously reported as poor substrates for the diazotransfer reaction gave corresponding diazo compounds in excellent yields with reagent 155.…”

RhII‐Catalyzed Cycloaddition of α‐Diazo Homophthalimides and Nitriles Delivers Oxazolo[5,4‐c]isoquinolin‐5(4H)‐one Scaffold

“…α-Diazo carbonyl compounds can be prepared in a variety of ways, most straightforward of which is the direct diazo transfer reaction requiring the substrate to be sufficiently α-C-H acidic and a source of diazo group (such as sulfonyl azides) to be employed. [7] While a wide range of substrates (strongly activated 1,3-dicarbonyl compounds in particular) can participate in diazo transfer reactions, [1] it came to our attention that for α-CH 2 imides and lactams, the transformation into respective α-diazo carbonyl products has largely not been described, with the exception of diazo transfer to 2,6-dihydroxypyridine. [8] Homophthalimides 5 have not been reported as substrates for diazo transfer reactions, the limited number of respective 4diazoisoquinoline-1,3-diones 6 described in the literature was prepared via the basic cleavage of respective N-tosylhydrazones.…”