The reaction of allyldialkyltelluronium bromides with anilines

Abstract

AllyldialkylteIluronium bromides were treated with aromatic amines in 1,2-dichloroethane, readily giving allyl awl amines in excellent yields.In recent years, there has been a remarkable development of new synthetic methods using organotellurium compounds [l]. It was found that telluronium ylides especially have many interesting applications in carbon-carbon bond formation [2]. Among them, dialkyltelluronium allylides were used for the synthesis of a,@-unsaturated epoxides [3]. However, there are no reports on the use of allyldialkyltelluronium salts as allylation reagents.Ogura and co-workers [4] have reported that benzenetellurinyl trifluoroacetate, when treated with allyltrimethylsilane in the presence of boron trifluoride etherate, gave allyl phenyl telluroxide. The latter was then treated in situ with an alkylamine to give the corresponding allylamine. We thought that the dialkyltelluronium group would be a better leaving group than the benzenetellurinyl group. Thei-efore, we studied the allylation reactions of aromatic amines with allyldialkyltelluronium bromides. Experimental results showed that aromatic allylamines can be obtained conveniently in excellent yields.

Ethyl [(2-hydroxyethylaminio)(2-hydroxyphenyl)methyl]phosphonate dihydrate

“…Aminophosphonic acids and their derivatives have received much attention because they are phosphorus analogs of naturally occurring aminocarboxylic acids (Palacios et al, 2000). Indeed, some potentially very powerful chelating agents, antibiotics, and pharmacological agents arise from aminophosphonic acids and their derivatives (Kurzak et al, 2000;Xu et al, 2000). A number of synthetic methods for the preparation of 1-aminoalkylphosphonates have been described Xu & Fu, 2001).…”

Reactions of unsymmetrical α‐diazo‐β‐diketones with imines: Syntheses of 4H‐1,3‐oxazin‐4‐ones

“…The acylketenes participate preferentially as the 4 component in inverse (diene LUMO controlled) Diels-Alder reactions with electron-rich and/or dipolar dieneophiles [4][5][6][7][8][9]. They are especially prone to undergo [2 + 4] cycloadditions with heterodienophiles, such as imines [4][5][6][7], nitriles [8], aldehydes and ketones [9,10], and thiones [11], as well as electron-rich alkenes or alkynes, for example, enamines [11] or enol ethers [12]. They can also react with some heterocumulenes [13], such as carbodiimides and isocyanates.…”

Mass spectral fragmentation of 2a,4‐disubstituted 2,2a,3,4‐tetrahydro‐2‐phenoxy‐1H‐azeto[2,1‐d][1,5]benzothiazepin‐1‐ones under electron impact ionization conditions

“…Some benzothiazepine and benzodiazepine derivatives show effective activities as potential central nervous system depressants, antipsychotic agents, antiinflamnatory and antiallergic agents, etc 1–7. Recently, we have paid much attention to investigations on the syntheses, stereochemistry and spectral properties of a series of tricyclic benzothiazepine derivatives 8–17.…”