Facile Synthesis of Phosphonates via Catalyst-Free Multicomponent Reactions in Water

Faramarz Rostami-Charati; Zinatossadat Hossaini

doi:10.1055/s-0032-1317078

Synlett, Inhaltsverzeichnis

Synlett 2012; 23(16): 2397-2399
DOI: 10.1055/s-0032-1317078

letter

Facile Synthesis of Phosphonates via Catalyst-Free Multicomponent Reactions in Water

Faramarz Rostami-Charati*

^aDepartment of Chemistry, Faculty of Science, Gonbad Kavous University, P.O. Box 163, Gonbad, Iran, Fax: +98(172)2224060 eMail: f_rostami_ch@yahoo.com

,

Zinatossadat Hossaini

^bDepartment of Chemistry, Qaemshahr Branch, Islamic Azad University, P.O. Box 163, Qaemshahr, Iran

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Stable derivatives of phosphonates were prepared using multicomponent reactions of dialkyl acetylenedicarboxylate with 1-(6-hydroxy-2-isopropenyl-1-benzofuran-yl)-1-ethanone or 4-hydroxycoumarin in the presence of trimethyl or triphenyl phosphite in water in good yields.

Key words

phosphonates - triphenyl phosphate - trimethyl phosphate - triethyl phosphate

Volltext

Referenzen

References and Notes

1a Mironov MA. QSAR Comb. Sci. 2006; 25: 423
1b Dömling A. Chem. Rev. 2006; 106: 17
1c Ramón DJ, Yus M. Angew. Chem. Int. Ed. 2005; 44: 1602
1d Orru RV. A, de Greef M. Synthesis 2003; 1471

2a Sikorski JA, Logusch EW In Handbook of Organophosphorus Chemistry . Engel R. Marcel Dekker; New York: 1992: 73
2b Eto M In Handbook of Organophosphorus Chemistry . Engel R. Marcel Dekker; New York: 1992: 807-873
2c Hinkle PC, McCarty RE. Sci. Am. 1978; 238: 104

3a Eto M. Organic and Biological Chemistry . CRC Press; Ohio: 1974: 1
3b Phosphorus and its Compounds . Vol. 2. Van Wazer JR. Interscience Publishers; New York: 1961
3c Engel R. Chem. Rev. 1977; 77: 349
3d Hildebrand R. The Role of Phosphonates in Living Systems . CRC Press; Boca Raton: 1983

4 Papazoglou ES. Handbook of Building Materials for Fire Protection . Harper CA. McGraw-Hill; New York: 2004. 4.1–4.88
5 Weil ED. Kirk-Othmer Encyclopedia of Chemical Technology . Vol. 4. John Wiley; New York: 1993: 976
6 Maryanoff BE, Reitz AB. Chem. Rev. 1989; 89: 863
7 Freeman GA, Rideout JL, Miller WH, Reardon JE. J. Med. Chem. 1992; 35: 3192
8 Kaboudin B, Nazari R. Tetrahedron Lett. 2001; 42: 8211
9 Kim DY, Rhie DY. Tetrahedron 1997; 53: 13603
10 Organic Phosphorus Compounds . Kosolapoff GM, Maier L. Wiley-Interscience; New York: 1972
11 Hudson HR In The Chemistry of Organophosphorus Compounds: Primary, Secondary and Tertiary Phosphines and Heterocyclic Organophosphorus(III) Compounds. Hantely FR. Wiley; New York: 1990: 386-472
12 Engel R. Synthesis of Carbon–Phosphorus Bonds . CRC Press; Boca Raton: 1998

13a Yavari I, Hossaini Z, Alizadeh A. Monatsh. Chem. 2006; 137: 1083
13b Yavari I, Mohtat B, Zare H. Mendeleev Commun. 2006; 15: 102
13c Alizadeh A, Yavari I. Mendeleev Commun. 2005; 14: 154
13d Yavari I, Alizadeh A. Synthesis 2004; 237
13e Yavari I, Alizadeh A, Anary-Abbasinejad M. Tetradhedron Lett. 2003; 44: 2877
13f Yavari I, Anary-Abbasinejad M, Hossaini Z. Org. Biomol. Chem. 2003; 1: 560

14 Yavari I, Hossaini Z, Karimi E. Monatsh. Chem. 2007; 138: 1267
15 Khaleghi F, Bin Din L, Rostami Charati F, Yaacob WA, Khalilzadeh MA, Skelton B, Makha M. Phytochem. Lett. 2011; 4: 254
16 Khaleghi F, Bin Din L, Jantan I, Yaacob WA, Khalilzadeh MA. Tetrahedron Lett. 2011; 52: 7182
17 General Procedure for the Preparation of Compounds 4 To a magnetically stirred solution of dialkyl acetylenedicarboxylate 2 (2 mmol) and 1-(6-hydroxy-2-isopropenyl-1-benzofuran-yl)-1-ethanone (1, 2 mmol) in H₂O was added trimethyl or triphenyl phosphite 3 (2 mmol). The reaction mixture was stirred for 6 h, and, after completion of reaction (monitored by TLC), the mixture was purified by silica gel column chromatography (Merck 230–400 mesh) using n-hexane–EtOAc as eluent to give compound 4. Representative Analytical Data for Compound 4a White powder; mp 138–140 °C; yield: 0.81 g (87%). IR (KBr): ν_max = 3225, 1740, 1735, 1724, 1678, 1587, 1128 cm^–1. Anal. Calcd (%) for C₂₁H₂₅O₁₀P (468.39): C, 53.85; H, 5.38. Found: C, 53.92; H, 5.47. ¹H NMR (500 MHz, CDCl₃): δ = 2.12 (3 H, s, Me), 2.58 (3 H, s, Me), 2.87 (3 H, d ³ J _HP = 11.2 Hz, MeO), 3.72 (3 H, s, MeO), 3.78 (3 H, d ³ J _HP = 11.2 Hz, OMe), 3.84 (3 H, s, MeO), 3.94 (1 H, dd ² J _HP = 20.4 Hz, ³ J _HH = 12.0 Hz, CH), 4.78 (1 H, d, ² J = 3.5 Hz, CH), 5.15 (1 H, dd, ³ J _HH = 12.0 Hz, ³ J _HP = 8.7 Hz, CH), 5.30 (1 H, s, CH), 5.73 (1 H, d, ² J = 3.5 Hz, CH), 7.82 (1 H, s, CH), 8.22 (1 H, s, OH). ¹³C NMR (125.7 MHz, CDCl₃): δ = 18.6 (Me), 27.3 (Me), 44.2 (CH), 48.5 (d, ¹ J _PC = 134.4 Hz, CH), 52.0 (OMe), 52.8 (d, ² J _PC = 8.2 Hz, MeO), 53.6 (MeO), 54.6 (d, ² J _PC = 8.2 Hz, MeO), 110.8 (d, ³ J _PC = 5.8 Hz, C), 111.4 (CH), 112.3 (CH₂), 117.5 (C), 121.0 (C), 122.4 (CH), 137.5 (C), 154.2 (C), 157.4 (C), 159.2 (C), 167.5 (d, ² J _PC = 5.4 Hz, C=O), 172.6 (d, ³ J _PC = 22.4 Hz, C=O), 192.8 (C=O). ³¹P NMR (202 MHz, CDCl₃): δ = 18.6. MS: m/z (%) = 468 (10) [M⁺], 359 (56), 109 (100), 31 (86)
18 General Procedure for the Preparation of Compounds 6 To a magnetically stirred solution of dialkyl acetylenedicarboxylate 2 (2 mmol) and 4-hydroxycoumarin (5, 2 mmol) in H₂O was added trimethyl or triphenyl phosphite 3 (2 mmol). The reaction mixture was then stirred for 5 h. After completion of reaction (monitored by TLC), the mixture was purified by silica gel column chromatog-raphy (Merck 230–400 mesh) using n-hexane–EtOAc as eluent to give compound 6. Representative Analytical Data for Compound 6a Colorless crystals; mp 185–187 °C; yield 0.70 g (85%). IR (KBr): ν_max = 3235, 1754, 1740, 1732 cm^–1. Anal. Calcd (%) for C₁₇H₁₉O₁₀P (414.30): C, 49.28; H, 4.62. Found: C, 49.36; H, 4.74. ¹H NMR (500 MHz, CDCl₃): δ = 2.92 (3 H, d, ³ J _HP = 11.2 Hz, MeO), 3.65 (3 H, s, MeO), 3.72 (3 H, d, ³ J _HP = 11.2 Hz, OMe), 3.85 (3 H, s, MeO), 3.92 (1 H, dd, ² J _HP = 20.4 Hz, ³ J _HH = 11.7 Hz, CH), 5.12 (1 H, dd, ³ J _HH = 11.7 Hz, ³ J _HP = 8.7 Hz, CH), 6.95–7.92 (4 H, m, 4 CH), 8.12 (1 H, s, OH). ¹³C NMR (125.7 MHz, CDCl₃): δ = 43.8 (CH), 48.2 (d, ¹ J _PC = 134.4 Hz, CH), 51.8 (OMe), 52.3 (d, ² J _PC = 8.2 Hz, MeO), 53.4 (MeO), 54.0 (d, ² J _PC = 8.2 Hz, MeO), 115.4 (C), 122.4 (CH), 123.8 (C), 125.4 (CH), 126.8 (CH), 127.5 (C), 132.6 (CH), 149.6 (C), 165.2 (C=O), 167.5 (d, ² J _PC = 5.4 Hz, C=O), 172.6 (d, ³ J _PC = 21.5 Hz, C=O). ³¹P NMR (202 MHz, CDCl₃): δ = 18.6. MS: m/z (%) = 414 (20) [M⁺], 252 (48), 162 (86), 31 (100)
19 Cadogan JI. G. Organophosphorus Reagents in Organic Synthesis . Academic Press; New York: 1977