An efficient and simple strategy toward the synthesis of highly functionalized compounds

Jmaï, Momtez; Dubreuil, Didier; Blot, Virginie; Lebreton, Jacques; M'rabet, Hedi

doi:10.1080/10426507.2021.1948850

Cited by 2 publications

(6 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1 2 3 4 5 In a recent paper, we described the synthesis of β-functionalized [(allyloxy)methyl]phosphonates 1 (Scheme 1 ), and studied their reactivity towards various nucleophiles such as amines or thiols to prepare linear original phosphonate compounds. 6…”

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

“…Cinnamyl ether, indene, and 2,5-dihydrofuran are structures also found in many natural and synthetic In a recent study, we described an efficient synthesis to access to a series of 22 functionalized phosphorylated compounds 1. 6 Because 1,3-dipolar cycloaddition has been increasingly used in organic synthesis to prepare original compounds, we planned to investigate the reactivity of some of our [(allyloxy)methyl]phosphonate compounds 1 as novel dipolarophiles in 1,3-dipolar cycloaddition involving nitrile oxides, nitrile imines, and nitrones as 1,3-dipoles (Scheme 1).…”

mentioning

confidence: 99%

“…Paper Synthesis 13 C NMR (100 MHz, CDCl 3 ):  = 169.8, 156.5, 130.6, 128.9, 128.9 (2 C), 127.0 (2 C), 88.5, 74.1 (d, J = 10.1 Hz), 66.3 (d, J = 165.6 Hz), 62.7 (d, J = 3.9 Hz), 62.6 (d, J = 3.9 Hz), 62.4, 40.5, 16.5 (d, J = 5. 6 1 H NMR (300 MHz, CDCl 3 ):  = 7.32 (dd, J = 7.9, 1.5 Hz, 1 H), 7.05 (t, J = 8.0 Hz, 1 H), 6.96 (dd, J = 8.2, 1.6 Hz, 1 H), 4.32-4.08 (m, 6 H), 3.95 (s, 2 H), 3.89 (d, J = 7.9 Hz, 2 H), 3.87 (s, 3 H), 3.78 (s, 4 H), 3.65 (d, J = 17.9 Hz, 1 H), 1.34-1.27 (m, 9 H). 31 P NMR (162 MHz, CDCl 3 ):  = 20.2.…”

mentioning

confidence: 99%

“…IR (neat): 2959 (C-H), 1731 (C=O), 1222 (C-O and C-N), 1024 (C-O) cm -1 .1 H NMR (400 MHz, CDCl 3 ):  diast1 = 7.26 (d, J = 1.9 Hz, 2 H),6.94 (td, J = 8.6, 4.9 Hz, 2 H), 4.24-4.11 (m, 2 H), 4.09-3.79 (m, 4 H), 3.76-3.69 (m, 6 H), 3.58-3.39 (m, 1 H), 2.78-2.54 (m, 2 H), 2.50 (s, 3 H), 1.25 (t, J = 7.1 Hz, 3 H).31 P NMR (162 MHz, CDCl 3 ):  diast1 = 22.8.19 F NMR (377 MHz, CDCl 3 ):  diast1 = -113.9.13 C NMR (100 MHz, CDCl 3 ):  diast1 = 172.0, 162.4 (d, J = 246.5 Hz), 133.6, 129.4 (d, J = 8.1 Hz, 2 C), 115.5 (d, J = 21.4, 2 C), 84.0, 75.1 (d, J = 10.0 Hz), 72.4, 65.4, 61.6, 52.9 (dd, J = 6.5, 2.9 Hz, 2 C), 45.0, 42.8, 14.1.1 H NMR (400 MHz, CDCl 3 ):  diast2 = 7.26 (d, J = 1.9 Hz, 2 H), 6.94 (td, J = 8.6, 4.9 Hz, 2 H), 4.24-4.11 (m, 2 H), 4.09-3.79 (m, 4 H), 3.76-3.69 (m, 6 H), 3.58-3.39 (m, 1 H), 2.78-2.54 (m, 2 H), 2.54 (s, 3 H), 1.25 (t, J = 7.1 Hz, 3 H).31 P NMR (162 MHz, CDCl 3 ):  diast2 = 23.1.19 F NMR (377 MHz, CDCl 3 ):  diast2 = -114.1.13 C NMR (100 MHz, CDCl 3 ):  diast2 = 170.9, 162.4 (d, J = 246.5 Hz), 133.2 (d, J = 3.1 Hz), 129.1 (d, J = 8.0 Hz, 2 C), 115.5 (d, J = 21.4 Hz, 2 C), 83.9, 75.6 (d, J = 9.8 Hz), 71.5, 65.2 (d, J = 164.5 Hz), 61.6, 52.9 (d, J = 6.4 Hz, 2 C), 45.8, 43.0, 14.0. HRMS (ESI + ): m/z [M + H] + calcd for C 17 H 26 FNO 7 P: 406.1431; found: 406.1420.Ethyl 5-(((Diethoxyphosphoryl)methoxy)methyl)-2-methyl-3-(4-(trifluoromethyl)phenyl)isoxazolidine-5-carboxylate (7g)By following general procedure 3, using diethyl [(allyloxy)methyl]phosphonate 1a (0.70 mmol, 0.20 g) and nitrone 6d (0.70 mmol, 0.14 g), a mixture of two inseparable diastereoisomers 7g was obtained.Yield: 0.23 g (69%); viscous oil; R f = 0.54 (EtOAc).IR (neat): 2984 (C-H), 1734 (C=O), 1254 (C-O and C-N), 1019 (C-O) cm -1 .…”

mentioning

confidence: 99%

“…[1][2][3][4][5] In a recent paper, we described the synthesis of -functionalized [(allyloxy)methyl]phosphonates 1 (Scheme 1), and studied their reactivity towards various nucleophiles such as amines or thiols to prepare linear original phosphonate compounds. 6 In this work, we investigate the behavior of these [(allyloxy)methyl]phosphonates 1 in several known reactions, including 1,3-dipolar cycloaddition, Heck coupling, metathesis, and radical coupling reactions, to prepare novel phosphorylated heterocyclic derivatives. The 1,3-dipolar cycloaddition process involving nitrile oxide, nitrile imine, and nitrone leads to the formation of five-membered heterocycles, which are present in a wide range of molecules with specific pharmaceutical and biological activities.…”

mentioning

confidence: 99%

See 4 more Smart Citations

Exploring the Reactivity of Substituted [(Allyloxy)methyl]phosphonates in Cycloaddition and Coupling Reactions

Blot,

M’rabet,

Jmai

et al. 2024

Synthesis

Self Cite

View full text Add to dashboard Cite

This paper describes the versatility of substituted [(allyloxy)methyl]phosphonates to open the way to the synthesis of original phosphonated molecules with heterocyclic architectures. In 1,3-dipolar cycloaddition reactions with nitrile oxides, nitrile imines, and nitrones, these [(allyloxy)methyl]phosphonates react as dipolarophiles to give, regioselectively, the corresponding isoxazolines, pyrazolines, and isoxazolidines. Transition-metal-catalyzed reactions, including inter- or intramolecular Heck coupling, provided access to cinnamyl- and indenyl-linked moieties and phosphonated benzo-fused oxacycles, respectively. Additionally, ring-closing metathesis reactions enabled the synthesis of 2,5-dihydrofurans with the phosphonate group at the anomeric position. In this work, 51 novel phosphorylated heterocyclic compounds, which may find significance in the pharmaceutical and agrochemical fields, were prepared.

show abstract

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

Exploring the Reactivity of Substituted [(Allyloxy)methyl]phosphonates in Cycloaddition and Coupling Reactions

Blot,

M’rabet,

Jmai

et al. 2024

Synthesis

Self Cite

View full text Add to dashboard Cite

show abstract

Quinquevalent phosphorus acids

Bałczewski,

Owsianik

2024

Organophosphorus Chemistry

View full text Add to dashboard Cite

This chapter shows, as in previous years, the most important achievements of the 2021 year in the area of organo-phosphorus compounds containing: three P–O bonds (Section 2: phosphoric acids and their derivatives), two P–O and one P–C bonds (Section 3: phosphonic acids and their derivatives) as well as one P–O and two P–C bonds (Section 4: phosphinic acids and their derivatives), in addition to the phosphoryl group P═O, present in all three groups of compounds. Each of the main sections covers “synthesis and reactions” including pure synthesis without applications, “synthesis and biological applications” and “synthesis and miscellaneous applications” including synthesis directed towards non-biological applications. At the end of each subsection, the corresponding achievements are shown for hetero-analogues in which phosphorus–oxygen bonds have been replaced by phosphorus–heteroatom P–X and/or P═Y bonds (X, Y = N, S or Se). The subsection on quinquevalent phosphorus acids and their derivatives as catalysts has been placed, as usual, at the end of the entire chapter, after a review of all three main groups of compounds. As in previous years, the area devoted to phosphoric and phosphonic acids and their derivatives dominated over a smaller section of phosphinic acids and their derivatives, and literature references for these sections remained at a ratio of 4 : 12 : 1. A dynamic, five-fold increase in the number of works, in the subject of chiral phosphoric acids as catalysts, has been recorded in this year.

show abstract

An efficient and simple strategy toward the synthesis of highly functionalized compounds

Cited by 2 publications

References 28 publications

Exploring the Reactivity of Substituted [(Allyloxy)methyl]phosphonates in Cycloaddition and Coupling Reactions

Exploring the Reactivity of Substituted [(Allyloxy)methyl]phosphonates in Cycloaddition and Coupling Reactions

Quinquevalent phosphorus acids

Contact Info

Product

Resources

About