A New Strategy for the Synthesis of Furan-3,4-dicarboxylic Acid [1]

Abstract

A facile route to furan-3,4-dicarboxylic acid is described. Dimethylmaleic anhydride (1) on NBS-bromination followed by aqueous KOH treatment gave bis(hydroxymethyl)maleic anhydride (3), which on intramolecular Mitsunobu ring closure followed by esterification and DDQ-oxidation furnished the desired esters of furan-3,4-dicarboxylic acid 7a/b.

Key words

2,3-bis(bromomethyl)maleic anhydride - intramolecular Mitsunobu ring closure - DDQ-oxidation - furan-3,4-dicarboxylic acid

1

NCL Communication No. 6620.

References

• 2 Song ZZ. Ho MS. Wong HNC. J. Org. Chem.  1994,  59:  3917 ; and references cited therein
• 3 Freeman-Cook KD. Halcomb RL. J. Org. Chem.  2000,  65:  6153 
• 4 Schultz AG. Motyka LA. Plummer M. J. Am. Chem. Soc.  1986,  108:  1056  and references cited therein
• 5 Tanis SP. Head DB. Tetrahedron Lett.  1982,  23:  5509 
• 6 Ingham CF. Massy-Westropp RA. Reynolds GD. Aust. J. Chem.  1974,  27:  1477 
• 7 Webb JS. inventors; US Patent  2732379.  ; Chem. Abstr. 1956, 50, 5999
• 8 Devys M. Barbier M. Parisot D. Heterocycles  1990,  31:  1485 
• 9 Tanis SP. Tetrahedron Lett.  1982,  23:  3115 
• 10a Walter L, Otto R, Richard R, and Franz Joseph K. inventors; Ger. Offen. DE  3143876.  ; Chem. Abstr. 1983, 99, 158275
• 10b Kentaro H. inventors; US Patent  4433154.  ; Chem. Abstr. 1984, 101, 23324
• 10c Hall IH. William WL. Rhyne KA. Knowles M. Pharm. Res.  1985,  233 
• 10d Manuel BZ, Antonio DMJ, Regorio DSM, Ulpiano MEP, Maria-Dolores JB, and Magali RF. inventors; PCT Int. Appl. WO 96  34870.  ; Chem. Abstr. 1997, 126, 59938
• 10e Galvez J. Garcia-Domenech R. Gomez-Lechon MJ. Castell JV. Theochem  2000,  504:  241 
• 11 Yan B. Zhang H.-J. Wang S.-B. Ni J.-Z. J. Photochem. Photobiol. A  1998,  116:  231 
• 12a Cook MJ. Forbes EJ. Tetrahedron  1968,  24:  4501 
• 12b Tochtermann W. Rosner P. Tetrahedron Lett.  1980,  21:  4905 
• 12c Tochtermann W. Rosner P. Chem. Ber.  1981,  114:  3725 
• 12d Jenneskens LW. Kostermans GBM. tenBrink HJ. Harmannus J. de’Wolf WH. Bickelhaupt F. J. Chem. Soc., Perkin Trans. 1  1985,  2119 
• 13 Reichstein T. Grussner A. Schindler K. Hardmeier E. Helv. Chim. Acta  1933,  16:  276 
• 14a Alder K. Rickert HF. Ber. Dtsch. Chem. Ges.  1937,  70:  1354 
• 14b Williams H. Kaufmann P. Mosher HS. J. Org. Chem.  1955,  20:  1139 
• 14c König H. Graf F. Weberndorfer V. Liebigs Ann. Chem.  1981,  668 
• 15 Kornfeld EC. Jones RG. J. Org. Chem.  1954,  19:  1671 
• 16 Bures E. Nieman JA. Yu S. Spinazze PG. Bontront J.-LJ. Hunt IR. Rauk A. Keay BA. J. Org. Chem.  1997,  62:  8750 ; and references cited therein
• 17a Gianturco MA. Friedel P. Giammarino AS. Tetrahedron  1964,  20:  1763 
• 17b Paquette LA. Russell RK. Burson RL. J. Am. Chem. Soc.  1975,  97:  6124 
• 18a Deshpande AM. Natu AA. Argade NP. J. Org. Chem.  1998,  63:  9557 
• 18b Deshpande SG. Argade NP. Synthesis  1999,  1306 
• 18c Deshpande AM. Natu AA. Argade NP. Heterocycles  1999,  51:  2159 
• 18d Deshpande AM. Natu AA. Argade NP. Synthesis  2001,  702 

1

NCL Communication No. 6620.

19

Deshpande, A. M.; Natu, A. A.; Argade, N. P., Unpublished results.