A Convenient and Easy Synthesis of γ-Nitro-α-Acetamido Esters

Roberto Ballini; Cesarino Balsamini; Giuseppe Diamantini; Nicoletta Savoretti

doi:10.1055/s-2005-861873

SHORTPAPER

A Convenient and Easy Synthesis of γ-Nitro-α-Acetamido Esters

Roberto Ballini*^a, Cesarino Balsamini^b, Giuseppe Diamantini^b, Nicoletta Savoretti^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 Istituto di Chimica Farmaceutica-Università degli Studi di Urbino ‘Carlo Bo’, Piazza Rinascimento 6, 61029 Urbino (PU), Italy

Abstract

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Abstract

A microwave-assisted synthesis of γ-nitro acetamido esters, under mild conditions and without solvent, is described. The desired products were obtained via Michael additions from the commercial methyl acetamidoacrylate and nitroalkanes.

Key words

microwave-assisted synthesis - α-amino acids - acetamidoacrylate - nitroalkane - Michael addition

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References

<A NAME="RZ21904SS-1">1</A> Adamczyk M. Johnson DD. Reddy RE. Tetrahedron: Asymmetry 2000, 11: 3063

<A NAME="RZ21904SS-2">2</A> Büchi G. Botkin JH. Lee GCM. Yakushijin K. J. Am. Chem. Soc. 1985, 107: 5555

<A NAME="RZ21904SS-3">3</A> Rowley M. Leeson PD. Williams BJ. Moore KW. Baker R. Tetrahedron 1992, 48: 3557

<A NAME="RZ21904SS-4">4</A> Rosini G. Ballini R. Synthesis 1988, 833

<A NAME="RZ21904SS-5">5</A> Rosini G. Ballini R. Petrini M. Marotta E. Righi P. Org. Prep. Proced. Int. 1990, 22: 707

<A NAME="RZ21904SS-6">6</A> Ballini R. Studies in Natural Products Chemistry Vol. 19: . Elsevier; Amsterdam: 1997. p.117-184

<A NAME="RZ21904SS-7">7</A> Ballini R. Synlett 1999, 1009

<A NAME="RZ21904SS-8">8</A> Ono N. The Nitro Group in Organic Synthesis John Wiley; New York: 2001.

<A NAME="RZ21904SS-9">9</A> Calderari G. Seebach D. Helv. Chim. Acta 1985, 68: 1592

<A NAME="RZ21904SS-10">10</A> Crossley MJ. Fung YM. Kyriakopoulos E. Potter JJ. J. Chem. Soc., Perkin Trans. 1 1998, 1123

<A NAME="RZ21904SS-11">11</A> Wieland T. Ohnacker G. Ziegler W. Chem. Ber. 1957, 90: 194

<A NAME="RZ21904SS-12">12</A> Crossley MJ. Fung YM. Potter JJ. Stamford AW. J. Chem. Soc., Perkin Trans. 1 1998, 1113

<A NAME="RZ21904SS-13">13</A> Ballini R. Balsamini C. Bartoccini F. Gianotti M. Martinelli C. Savoretti N. Synthesis 2005, 296

<A NAME="RZ21904SS-14A">14a</A> Balsamini C. Duranti E. Mariani L. Salvatori A. Spadoni G. Synthesis 1990, 779

<A NAME="RZ21904SS-14B">14b</A> Jayakanthan K. Madhusudanan KP. Vankar YD. Tetrahedron 2004, 60: 397

<A NAME="RZ21904SS-15">15</A> Ballini R. Bosica G. J. Chem. Res., Synop. 1993, 435