Phosphorylation of some new acenaphthenequinone derivatives

Abstract

Acenaphthenequinone reacted with diazofluorene, diphenyldiazomethane, phenybenzoyldiazomethane, phenacyl chloride, o-nitrobenzyl chloride, and diazohydroindenedione to give new oxadiazole, ketoepoxide and dioxadiazepine derivatives. They reacted with triphenylphosphine and triethylphosphite to give new organophosphorus compounds containing a six-membered or four-membered phosphorane ring. The structures were elucidated using IR, UV, NMR, and mass spectra, and elemental analyses.Many earlier studies have been reported on the reactions of phenanthrenequinones with diazomethane. Arndt [1] found that it gave the monoethylene oxide derivative when the reaction was carried out using ether and a small amount of methanol. Reinvestigation of the same reaction [2], using dioxirane containing a small amount of methanol, gave monospiroepoxy ketone, and in tetrahydrofuran with a small amount of lithium chloride the product was the bis-epoxide, while in the presence of a large amount of methanol ring expansion took place.The reaction of some derivatives of diazomethane with phenanthrenequinone [2-4] gave a methylenedioxy derivative. The reaction of diphenyldiazomethane and di(p-chlorophenyl)diazomethane with phenanthrenequinone showed that the structures must be corrected to the ketoepoxide [5]. 3,6-Dibromo-9,10-phenanthrene reacted with diazoalkanes to give the corresponding ketoepoxide derivatives [6]. The o-methyl ether of isatin reacted with diazomethane to furnish a quinoline derivative as the major product, together with a spirooxirane derivative [7]. It has been reported [8] that p-chloroacetophenone reacted with diphenyldiazomethane and diazofluorene in benzene in the presence of copper bronze to give nitrogen-and halogen-free new compounds and p-chlorophenol. The reaction of diazomethane derivatives with 1,2-naphthoquinone-4-sulfonic acid in benzene gave α-ketoepoxides, cyclopropane, and methylenedioxy derivatives, accompanied

Conversion of Azides into Diazo Compounds in Water

“…The next test was to probe the tolerance of electrophiles such as aldehydes, 18 α-chloroesters, 19 and disulfide bonds, 20 and epoxides, 21 in the presence of the nucleophilic phosphorus of phosphinoester 1 . Again, we found phosphinoester 1 to be highly chemoselective, converting azido-glycine derivatives into their corresponding diazo compounds without notable side reactivity (Table 3).…”

Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds­ and Complexes Based on Acenaphthylene-1,2-dione

“…In 2009, El-Sawi et al 75 investigated the reactions of 1 with diazomethane derivatives 151 and phenacyl chlorides 152 to afford new oxadiazole derivatives 153 and 154. These products reacted with triphenylphosphine (126) and triethyl phosphite (155), respectively, to give new organophosphorus compounds containing a six-membered 156 (73% yield) or four-membered phosphorane ring 157 (60% yield) (Scheme 55).…”

Diazafluorene in 1,3-dipolar cycloaddiction reactions: short review

“…According to literature, reactions of diazafluorene with dipolarophiles, which have a heteroatomic core, occur mostly on O=C< [20,22] parts, creating oxadiazoline, -P=C< (phosphadiazoline) [23], and S=C< (thiadiazoline) [21,25].…”

“…Yet another example of a similar reaction is cycloaddition with acenaphthene quinine (44). The process is realised with benzene as a solvent as well as at a boiling temperature, and has a yield of 35% [22].…”

“…The process of 1,3-dipolar cycloaddition (in brief 1,3DC) is the most universal method of creating five membered carbo-and heterocyclic compounds [13]. When using diazafluorene (as 1,3-dipole) as an addent, one can produce connections of a pyrazoline [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] skeleton within its structure. Those connections are valuable from a practical perspective [1][2][3][4][5][6][7][8][9][10].…”