Chemistry of phosphorus ylides 21 new route for the synthesis of azetidinones. Reaction of phosphonium ylides with benzil-,o-naphthoquinone-, and triketonemonoanils

Abstract

Active vinylidenetriphenylphosphoranes are nucleophilic reagents which can be considered as versatile synthons for the synthesis of new heterocycles. The active phosphacumulene

Chemistry of Phosphorus Ylides: Part 41 Synthesis of Antimicrobial Agents from the Reaction of Aminoantipyrine, Coumarin- and Quinoline-carbaldehyde with Phosphacumulene and Phosphaallene Ylides

“…The 31 P NMR shift of 15a was at δ 15.96 ppm which fits with a phosphorane on 4-membered ring. 39 On the other hand, the reaction of compound 12 with (2-oxovinylidene)-triphenylphosphorane (2b) afforded only one product, 2-[(2-chloroquinolin-3-yl)methylidene]-4-(triphenyl-λ 5 -phosphanylidene)cyclobutane-1,3-dione (15b) together with triphenylphosphane oxide. Moreover, the proposed structure of 15b was further unequivocally confirmed by X-ray crystallography (Fig.…”

Chemistry of Phosphorus Ylides, Part 30. Reaction of Camphorquinone Derivatives with Active Phosphacumulenes and Stabilized Phosphonium Ylides

“…The most interesting aspects of these compounds are their applications in permanent restorative dental resins (1)(2)(3) , as substrate in dental cements (4,5) , dentin-bonding agents (6,7) , and in root canal filling materials (1) . In continuation to our work in the field of phosphonium ylides (8)(9)(10)(11)(12)(13)(14) , the present investigation has aimed to investigate the reaction of camphorquinone and its derivatives, such as, 1,7,7-trimethyl-bicycle [2.2.1]-heptane-2,3-dione (1), 3-(2-phenylhydrazono)-1,7,7-trimethylbicyclo [2.2.1]-heptan-2-one (13), and 3-(hydroxyimino)-1,7,7-trimethylbicyclo[2.2.1] heptan-2-one (16) with the active nucleophilic phosphacumulene reagents, namely (Nphenyliminovinylidene) -(2a), (2-oxovinylidene) -(2b), and (2-thioxovinylidene) -triphenylphosphorane (2c). These active phosphacumulene ylides are important phosphorus reagents, used for the synthesis of heterocyclic phosphorus compounds (15,16) .…”

“…The identity of compound 12 was supported by molecular weight determination (MS) as well as spectroscopic data, which are compatible with the assigned structure. The IR spectrum of 12 (KBr, cm -1 ) disclosed the presence of strong absorption bands at 1667 (C=O, lactone), and 1662 cm -1 (C=O, ester (1) is explained by the nucleophilic addition of phosphonium ylide 6a to one of the carbonyl groups of 1 to give the betaine (7), which is cyclized to the oxaphosphetane (8). Part of 8 decomposed to give the alkene (9) together with triphenylphosphine oxide.…”

Chemistry of phosphorus ylides 31: Reaction of azidocoumarin with active phosphonium ylides, synthesis and antitumour activities of chromenones

“…Generation of azetes from 1,2,3-triazine derivatives has been previously observed. 37,38 [Physical and spectroscopic data are provided in the experimental section].…”