Cycloaddition/Aromatization Sequence for the Synthesis of 2,3-Disubstituted Benzenephosphonates

Elise Villemin; Jacqueline Marchand-Brynaert

doi:10.1055/s-0031-1289757

Synthesis, Table of Contents

Synthesis 2012; 44(12): 1923-1927
DOI: 10.1055/s-0031-1289757

paper

Cycloaddition/Aromatization Sequence for the Synthesis of 2,3-Disubstituted Benzenephosphonates

Authors

Elise Villemin

Université catholique de Louvain, Institute of Condensed Matter and Nanosciences (ICMN), Molecules, Solids and Reactivity (MOST), Bâtiment Lavoisier, Place Louis Pasteur, L4.01.02, 1348 Louvain-la-Neuve, Belgium, Fax: +32(10)474168 Email: Jacqueline.marchand@uclouvain.be
Jacqueline Marchand-Brynaert*

Université catholique de Louvain, Institute of Condensed Matter and Nanosciences (ICMN), Molecules, Solids and Reactivity (MOST), Bâtiment Lavoisier, Place Louis Pasteur, L4.01.02, 1348 Louvain-la-Neuve, Belgium, Fax: +32(10)474168 Email: Jacqueline.marchand@uclouvain.be

Abstract

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Abstract

The [4+2] cycloaddition of diethyl 1-phosphonobuta-1,3-diene with tetracyanoethylene, (E)-1,4-diphenylbut-2-ene-1,4-dione, N-phenylmaleimide, and dialkyl acetylenedicarboxylates is described. For the last two cases, treatment of the cycloadducts with nitrobenzene and a palladium catalyst allows the aromatization. Selective deprotections lead to phthalimide/phthalate derivatives with an ortho-phosphonic acid function.

Key words

cycloaddition - Diels–Alder reaction - phosphorus - bicyclic compounds - carboxylic acids - hydrolysis

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References

References

1a Nagarajan R, Pratt RF. Biochemistry 2004; 43: 9664
1b Stankovic CJ, Surendran N, Lunney EA, Plummer MS, Para KS, Shahripour AS, Fergus JH, Marks JS, Herrera R, Hubbell SE, Humblet C, Saltiel AR, Stewart BH, Sawyer TK. Bioorg. Med. Chem. Lett. 1997; 14: 1909
1c Ma D, Zhu W. J. Org. Chem. 2001; 66: 348
1d Thurieau C, Simonet S, Paladino J, Prost J.-F, Verbeuren T, Fauchère J.-L. J. Med. Chem. 1994; 37: 625

2a Bock T, Moehwald H, Muelhaupt R. Macromol. Chem. Phys. 2007; 208: 1324
2b Consiglio GA, Failla S, Finocchiaro P, Siracusa V. Phosphorus, Sulfur Silicon Relat. Elem. 2002; 177: 2561
2c Onouchi H, Miyagawa T, Furuko A, Maeda K, Yashima E. J. Am. Chem. Soc. 2005; 127: 2960
2d Allcock HR, Hofmann MA, Ambler CM, Morford RV. Macromolecules 2002; 35: 3484

3a Chandrasekhar V, Sasikumar P, Senapati T, Dey A. Inorg. Chim. Acta 2010; 363: 2920
3b Ouellett W, Wang G, Liu X, Yee GT, O’Connor CJ, Zubieta J. Inorg. Chem. 2009; 48: 953
3c Latham K, Coyle AM, Rix CJ, Fowless A, White JM. Polyhedron 2007; 26: 222
3d Zakeeruddin SM, Nazeeruddin MK, Pechy P, Rotzinger FP, Humphry-Baker R, Kalyanasundaram K, Grätzel M, Shklover V, Haibach T. Inorg. Chem. 1997; 36: 5937

4 Bhattachary AK, Thyarajan G. Chem. Rev. 1981; 81: 415

5a Prim D, Campagne J.-M, Joseph D, Andriolettti B. Tetrahedron 2002; 58: 2041
5b Kohler MC, Sokol JG, Stockland RA. Jr. Tetrahedron Lett. 2009; 50: 457
5c Goosen LJ, Dezfuli MK. Synlett 2005; 445

6 Kagayama T, Nakano A, Sakaguchi S, Ishii Y. Org. Lett. 2006; 8: 407
7 Jiao X.-Y, Bentrude WG. J. Org. Chem. 2003; 68: 3303
8 Defacqz N, de Bueger B, Touillaux R, Cordi A, Marchand-Brynaert J. Synthesis 1999; 1368

9a Bruyneel F, D’Auria L, Payen O, Courtoy PJ, Marchand-Brynaert J. ChemBioChem 2010; 11: 1451
9b Lagadic E, Garcia Y, Marchand-Brynaert J. Synthesis 2012; 44: 93

10a Jayasundera KP, Watson AJ, Taylor CM. Tetrahedron Lett. 2005; 46: 4311
10b Taylor CM, Watson AJ. Curr. Org. Chem. 2004; 8: 623

11a Monbaliu J.-C, Villemin E, Elias B, Marchand-Brynaert J In Targets in Heterocyclic Systems . Vol. 14. Attanasi OA, Spinelli D. Springer; Berlin: 2010: 49
11b Monbaliu J.-C, Tinant B, Marchand-Brynaert J. J. Org. Chem. 2010; 75: 5478
11c Villemin E, Elias B, Robiette R, Robeyns K, Herent M.-F, Habib-Jiwan J.-L, Marchand-Brynaert J. Tetrahedron Lett. 2011; 52: 5140

12 Griffin CE, Daniewski WM. J. Org. Chem. 1970; 35: 1691

13a Monbaliu J.-C, Cukalovic A, Marchand-Brynaert J, Stevens CV. Tetrahedron Lett. 2010; 51: 5830
13b Monbaliu J.-C, Tinant B, Peeters D, Marchand-Brynaert J. Tetrahedron Lett. 2010; 51: 1052
13c Monbaliu J.-C, Marchand-Brynaert J. Synthesis 2009; 1876

14 Principato B, Maffei M, Siv C, Buono G, Peiffer G. Tetrahedron 1996; 52: 2087
15 Vanden EydenJ.-J, D’Orazio R, Van Haverbeke Y. Tetrahedron 1994; 50: 2479
16 Suzuki H, Nomura M, Tokunaga K, Hashiba I (Nissan Chem. Ind. Ltd.) US Patent 5880309A1, 1999 ; Chem. Abstr. 1998, 129, 149095
17 Odorisio P, Andrews S, Thompson TF, Wu S, Thanki P, Rane DM, Joseph D, Wang J (Ciba Corp.) WO 2009121796 A1, 2009 ; Chem. Abstr. 2009, 151, 426211

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