Nitroalkanes and Dimethyl Maleate as Source of 3-Alkyl Succinic Anhydrides and (E)-3-Alkylidene Succinic Anhydrides

Roberto Ballini; Giovanna Bosica; Dennis Fiorini; Paolo Righi

doi:10.1055/s-2002-23548

PAPER

Nitroalkanes and Dimethyl Maleate as Source of 3-Alkyl Succinic Anhydrides and (E)-3-Alkylidene Succinic Anhydrides

Roberto Ballini*^a, Giovanna Bosica^a, Dennis Fiorini^a, Paolo Righi^b
^a Dipartimento di Scienze Chimiche dell’Università, Via S. Agostino 1, 62032 Camerino (MC), Italy
Fax: +39(0737)402297; e-Mail: roberto.ballini@unicam.it;
^b Dipartimento di Chimica Organica ”A. Mangini" dell’Università, V.le Risorgimento 4, 40136 Bologna, Italy

Abstract

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Abstract

Nitroalkanes react with dimethyl maleate giving a tandem Michael addition/elimination of nitrous acid. The obtained (E)-2-alkylidene dimethyl succinates are: (i) reduced to the corresponding 2-alkyl dimethyl succinates which after hydrolysis produce 1,4-dicarboxylic acids that are prone to convert into the corresponding 3-alkyl succinic anhydrides or (ii) hydrolysed to (E)-2-alkylidene-succinic acids that are easily cyclised to (E)-3-alkylidene succinic anhydrides.

Key words

nitroalkanes - 3-alkyl succinic anhydrides - 3-alkylidene succinic anhydrides - dimethyl maleate - heterocyclic compounds

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References

1 Devlin JP. Ollis WD. Thorpe JE. Wood RS. Broughton BJ. Warren PJ. Wooldbridge KRH. Wright DE. J. Chem. Soc., Perkin Trans. 1 1975, 830

2 Broughton BJ. Warren PJ. Wooldbridge KRH. Wright DE. Ollis WD. Wood RJ. J. Chem. Soc., Perkin Trans 1 1975, 842

3 Porter NA. Scott DM. Rosenstein IJ. Giese B. Veit A. Zeitz HG. J. Am. Chem. Soc. 1991, 113: 1791

4 Levy DE. Lapierre F. Liang W. Ye W. Lange CW. Li X. Grobelny D. Casabonne M. Tyrrell D. Holme K. Nadzan A. Galardy RE. J. Med. Chem. 1998, 41: 199

5 Groutas WC. Brubaker MJ. Stanga MA. Castrisos JC. Crowley JP. Schatz EJ. J. Med. Chem. 1989, 32: 1607

6 Bates RB. Cuther RS. Freeman RM. J. Org. Chem. 1977, 42: 4162

7a Kofron WG. Wideman LG. J. Org. Chem. 1972, 37: 555

7b Sabitha G. Srividya R. Yadav JS. Tetrahedron 1999, 55: 4015

7c Chen Y. Deng L. J. Am. Chem. Soc. 2001, 123: 11302

7d Bergmeier SC. Ismail KA. Synthesis 2000, 1369

8 Giese B. Kretzchmar G. Meixner J. Chem. Ber. 1980, 113: 2787

9 Cermenati L. Mella M. Albini A. Tetrahedron 1998, 54: 2575

10 Horning EC. Walker GN. J. Am. Chem. Soc. 1952, 74: 5147

11 Doulut S. Dubuc I. Rodriguez M. Vecchini F. Fulcrand H. Bareli H. Checler F. Bourdel E. Aumelas A. Lallement JC. Kitabgi P. Costentin J. Martinez J. J. Med. Chem. 1993, 36: 1369

12 Nogi T. Tsuji J. Tetrahedron 1969, 25: 4099

13a Ballini R. Marcantoni E. Perella S. J. Org. Chem. 1999, 64: 2954

13b Ballini R. Barboni L. Bosica G. Petrini M. Synlett 2000, 391

13c Ballini R. Bosica G. Masè A. Petrini M. Eur. J. Org. Chem. 2000, 2927

13d Ballini R. Bosica G. Fiorini D. Giarlo G. Synthesis 2001, 2003

14 Ballini R. Rinaldi A. Tetrahedron Lett. 1994, 35: 9247

15 Freiser LF. Martin EL. Org. Synth. Coll. Vol. 2 John Wiley & Sons; London: 1957. p.560