A New Approach to Di- and Tetrasubstituted
2,3-Dihydropyridin-4(1H)-ones through
Aza-Diels-Alder Reaction Promoted by Silicon Tetrachloride

Antonio Massa; Vincenzo de Sio; Rosaria Villano; M. Rosaria Acocella; Laura Palombi; Giusi Sellitto; Antonella Peduto; Rosanna Filosa; Paolo De Capraris; Arrigo Scettri

doi:10.1055/s-0028-1087677

PAPER

A New Approach to Di- and Tetrasubstituted 2,3-Dihydropyridin-4(1H)-ones through Aza-Diels-Alder Reaction Promoted by Silicon Tetrachloride

Antonio Massa*^a, Vincenzo de Sio^a, Rosaria Villano^a,b, M. Rosaria Acocella^a, Laura Palombi^a, Giusi Sellitto^c, Antonella Peduto^c, Rosanna Filosa^c, Paolo De Capraris^c, Arrigo Scettri^a
^a Dipartimento di Chimica, Università di Salerno, Via Ponte Don Melillo, 84084 Fisciano, Salerno, Italy
Fax: +39(089)969603; e-Mail: amassa@unisa.it;
^b Istituto di Chimica Biomolecolare-CNR, Trav. La Crucca, 07040 Li Punti, Sassari, Italy
^c Dipartimento di Scienze Farmaceutiche, Università di Salerno, Via Ponte Don Melillo, 84084 Fisciano, Salerno, Italy

Abstract

All articles of this category

Abstract

Silicon tetrachloride promotes an aza-Diels-Alder reaction with a range of imines and Danishefsky’s diene or an alkylated derivative, giving the desired products in good to excellent yields.

Key words

aza-Diels-Alder reaction - heterocycles - silicon tetrachloride

Full Text

References

<A NAME="RP10008SS-1A">1a</A> Organic Synthesis Highlights Waldmann H. VCH; Weinheim: 1995. 2nd ed.. p.37

<A NAME="RP10008SS-1B">1b</A> Weinreb SM. In Comprehensive Organic Synthesis Vol. 5: Trost BM. Fleming I. Semmelhack MF. Pergamon; Oxford: 1991. Chap. 2.

<A NAME="RP10008SS-1C">1c</A> Weinreb SM. In Comprehensive Organic Synthesis Vol. 5: Trost BM. Fleming I. Semmelhack MF. Pergamon; Oxford: 1991. Chap. 9.

<A NAME="RP10008SS-1D">1d</A> Weinreb SM. In Comprehensive Organic Synthesis Vol. 5: Trost BM. Fleming I. Semmelhack MF. Pergamon; Oxford: 1991. p.401

<A NAME="RP10008SS-1E">1e</A> Boger DL. Weinreb SM. Hetero Diels-Alder Methodology in Organic Synthesis Academic Press; San Diego: 1987.

For reviews:

<A NAME="RP10008SS-2A">2a</A> Rubiralta M. Giralt E. Diez A. Piperidine: Structure, Preparation, and Synthetic Applications of Piperidine and Its Derivatives Elsevier; Amsterdam: 1991.

<A NAME="RP10008SS-2B">2b</A> Bailey PD. Millwood PA. Smith PD. Chem. Commun. 1998, 633

<A NAME="RP10008SS-2C">2c</A> Jorgensen KA. Angew. Chem. Int. Ed. 2000, 39: 3558

<A NAME="RP10008SS-3A">3a</A> Jurcik V. Arai K. Salter MM. YamashitaY . Kobayashi S. Adv. Synth. Catal. 2008, 350: 647

<A NAME="RP10008SS-3B">3b</A> Patmore NJ. Hague C. Cotgreave JH. Mahon MF. Frost CG. Weller AS. Chem. Eur. J. 2002, 8: 2088

<A NAME="RP10008SS-3C">3c</A> Collin J. Jaber N. Lannou MI. Tetrahedron Lett. 2001, 42: 7405

<A NAME="RP10008SS-3D">3d</A> Laurent-Robert H. Garrigues B. Dubac J. Synlett 2000, 1160

<A NAME="RP10008SS-3E">3e</A> Ali T. Chauhan KK. Frost CG. Tetrahedron Lett. 1999, 40: 5621

<A NAME="RP10008SS-3F">3f</A> Bari LD. Guillarme S. Hermitage S. Howard JAK. Jay DA. Pescitelli G. Whiting A. Yufit DS. Synlett 2004, 708

<A NAME="RP10008SS-3G">3g</A> Hattori K. Yamamoto H. Synlett 1993, 129

<A NAME="RP10008SS-3H">3h</A> Kobayashi S. Araki M. Ishitani H. Nagayama S. Hachiya I. Synlett 1995, 233

<A NAME="RP10008SS-3I">3i</A> Morgan PE. McCague R. Whiting A. J. Chem. Soc., Perkin Trans. 1 2000, 515

<A NAME="RP10008SS-3J">3j</A> Ishihara K. Miyata M. Hattori K. Tada T. Yamamoto H. J. Am. Chem. Soc. 1994, 116: 10520

With a solid catalyst:

<A NAME="RP10008SS-3K">3k</A> Kumareswaran R. Reddy BG. Vankar YD. Tetrahedron Lett. 2001, 42: 7493

<A NAME="RP10008SS-3L">3l</A> Wang Y. Wilson SR. Tetrahedron Lett. 1997, 38: 4021

<A NAME="RP10008SS-4A">4a</A> Loncaric C. Manabe K. Kobayashi S. Chem. Commun. 2003, 574

<A NAME="RP10008SS-4B">4b</A> Loncaric C. Manabe K. Kobayashi S. Adv. Synth. Catal. 2003, 345: 475

<A NAME="RP10008SS-4C">4c</A> Lock R. Waldmann H. Tetrahedron Lett. 1996, 37: 2753

<A NAME="RP10008SS-5A">5a</A> Jurcik V. Wilhelm R. Org. Biomol. Chem. 2005, 3: 239

<A NAME="RP10008SS-5B">5b</A> Zulfiqar F. Kitazume T. Green Chem. 2000, 2: 137

<A NAME="RP10008SS-6">6</A> Aza-Diels-Alder reaction in MeOH without catalyst: Yuan Y. Li X. Ding K. Org. Lett. 2002, 4: 3309

<A NAME="RP10008SS-7">7</A> Chiral Brønsted acid catalyzed aza-Diels-Alder reaction: Itoh J. Fuchibe K. Akiyama T. Angew. Chem. Int. Ed. 2006, 45: 4796

<A NAME="RP10008SS-8">8</A> Hattori K. Yamamoto H. J. Org. Chem. 1992, 57: 3264

<A NAME="RP10008SS-9A">9a</A> Kobayashi S. Komiyama S. Ishitani H. Angew. Chem. Int. Ed. 1998, 37: 979

<A NAME="RP10008SS-9B">9b</A> Kobayashi S. Kusakabe K.-i. Komiyama S. Ishitani H. J. Org. Chem. 1999, 64: 4220

<A NAME="RP10008SS-9C">9c</A> Kobayashi S. Kusakabe K.-i. Komiyama S. Ishitani H. Org. Lett. 2000, 2: 1225

<A NAME="RP10008SS-9D">9d</A> Ishitani H. Kobayashi S. Tetrahedron Lett. 1996, 37: 7357

<A NAME="RP10008SS-9E">9e</A> Kobayashi S. Ishitani H. Chem. Rev. 1999, 99: 1069

<A NAME="RP10008SS-9F">9f</A> Yao S. Johannsen M. Hazell RG. Jørgensen KA. Angew. Chem. Int. Ed. 1998, 37: 3121

<A NAME="RP10008SS-9G">9g</A> Yao S. Saaby S. Hazell RG. Jørgensen KA. Chem. Eur. J. 2000, 6: 2435

<A NAME="RP10008SS-9H">9h</A> Jørgensen KA. Angew. Chem. Int. Ed. 2000, 39: 3558

<A NAME="RP10008SS-9I">9i</A> Buonora P. Olsen J.-C. Oh T. Tetrahedron 2001, 57: 6099

<A NAME="RP10008SS-9J">9j</A> Josephsohn NS. Snapper ML. Hoveyda AH. J. Am. Chem. Soc. 2003, 125: 4018

<A NAME="RP10008SS-9K">9k</A> Mancheno OG. Arrayas RG. Carretero JC. J. Am. Chem. Soc. 2004, 126: 456

<A NAME="RP10008SS-9L">9l</A> Guillarme S. Whiting A. Synlett 2004, 711

<A NAME="RP10008SS-9M">9m</A> Bromidge S. Wilson PC. Whiting A. Tetrahedron Lett. 1998, 39: 8905

<A NAME="RP10008SS-9N">9n</A> Bundu A. Guillarme S. Hannan J. Wan H. Whiting A. Tetrahedron Lett. 2003, 44: 7849

<A NAME="RP10008SS-10A">10a</A> Andreassen T. Haland T. Hansen LK. Gautun OR. Tetrahedron Lett. 2007, 48: 8413

<A NAME="RP10008SS-10B">10b</A> Rowland GB. Rowland EB. Zhang O. Antilla JC. Curr. Org. Chem. 2006, 10: 9

<A NAME="RP10008SS-10C">10c</A> Timmons C. Kattuboina A. McPherson L. Mills J. Li G. Tetrahedron 2005, 61: 11837

<A NAME="RP10008SS-10D">10d</A> Yao S. Saaby S. Hazell RG. Jørgensen KA. Chem. Eur. J. 2000, 6: 2435

<A NAME="RP10008SS-10E">10e</A> Badorrey C. Cativiela C. Diaz-de-Villegas MD. Galvez JA. Tetrahedron 1999, 55: 7601

<A NAME="RP10008SS-10F">10f</A> Yu L. Li J. Ramirez J. Chen D. Wang PG. J. Org. Chem. 1997, 62: 903

<A NAME="RP10008SS-10G">10g</A> Heintzelman GR. Weinreb SM. Parvez M. J. Org. Chem. 1996, 61: 4594

<A NAME="RP10008SS-10H">10h</A> McFarlane AK. Thomas G. Whiting A. J. Chem. Soc., Perkin Trans. 1 1995, 2803

<A NAME="RP10008SS-10I">10i</A> Danishefsky S. Langer ME. Vogel C. Tetrahedron Lett. 1985, 26: 5983

<A NAME="RP10008SS-11A">11a</A> Clark RC. Pfeiffer SS. Boger DL. J. Am. Chem. Soc. 2006, 128: 2587

<A NAME="RP10008SS-11B">11b</A> Ishimaru K. Yamamoto Y. Akiba K. Tetrahedron 1997, 53: 5423

<A NAME="RP10008SS-12A">12a</A> Denmark SE. Beutner GL. Angew. Chem. Int. Ed. 2008, 47: 1560

<A NAME="RP10008SS-12B">12b</A> Denmark SE. Wynn T. J. Am. Chem. Soc. 2001, 123: 6199

<A NAME="RP10008SS-12C">12c</A> Denmark SE. Wynn T. Beutner GL. J. Am. Chem. Soc. 2002, 124: 13405

<A NAME="RP10008SS-13">13</A> Acocella MR. De Rosa M. Massa A. Palombi L. Villano R. Scettri A. Tetrahedron 2005, 61: 4091

<A NAME="RP10008SS-14">14</A> Scettri A. Acocella MR. Palombi L. Scalera C. Villano R. Massa A. Adv. Synth. Catal. 2006, 348: 2229

<A NAME="RP10008SS-15A">15a</A> Etayo P. Badorrey R. Díaz-de-Villegas MD. Gálvez JA. Eur. J. Org. Chem. 2008, 6008