The Use of Magnesium Nitride
for the Synthesis of Enantiomerically Pure 1,4-Dihydropyridines
via the Hantzsch Reaction

Sha Long; Mauro Panunzio; Alessandra Petroli; Wenling Qin; Zhining Xia

doi:10.1055/s-0030-1258462

PAPER

The Use of Magnesium Nitride for the Synthesis of Enantiomerically Pure 1,4-Dihydropyridines via the Hantzsch Reaction

Sha Long^a, Mauro Panunzio*^a, Alessandra Petroli^a, Wenling Qin^b, Zhining Xia*^b
^a ISOF-CNR, Dipartimento di Chimica ‘G. Ciamician’, Via Selmi 2, 40126 Bologna, Italy
Fax: +39(051)2099456; e-Mail: mauro.panunzio@unibo.it;
^b Department of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 400044, P. R. of China

Abstract

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Abstract

Enantiomerically pure 1,4-dihydropyridines are prepared taking advantage of magnesium nitride as a useful and convenient source of ‘solid ammonia’. The products possess various substituents at carbons 3, 4 and 5 of the dihydropyridine moiety.

Key words

1,4-dihydropyridines - magnesium nitride - multicomponent reaction - Hantzsch esters - one-pot condensation

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References

<A NAME="RZ08811SS-1A">1a</A> Yamamoto T. Niwa S. Ohno S. Onishi T. Matsueda H. Koganei H. Uneyama H. Fujita S. Takeda T. Kito M. Ono Y. Saitou Y. Takahara A. Iwata S. Shoji M. Bioorg. Med. Chem. Lett. 2006, 16: 798

<A NAME="RZ08811SS-1B">1b</A> Dagnino L. Li-Kwong-Ken MC. Wolowyk MW. Wynn H. Triggle CR. Knaus EE. J. Med. Chem. 1986, 29: 2524

<A NAME="RZ08811SS-1C">1c</A> Dagnino L. Li-Kwong-Ken MC. Wynn H. Wolowyk MW. Triggle CR. Knaus EE. J. Med. Chem. 1987, 30: 640

<A NAME="RZ08811SS-2">2</A> Choi S.-J. Cho J.-H. Im I. Lee S.-D. Jang J.-Y. Oh Y.-M. Jung Y.-K. Jeon E.-S. Kim Y.-C. Eur. J. Med. Chem. 2010, 45: 2578

<A NAME="RZ08811SS-3">3</A> Iwanami M. Shibanuma T. Fujimoto M. Kaway R. Tamazawa K. Takenaka T. Takahashi K. Murakami M. Chem. Pharm. Bull. 1979, 27: 1426

<A NAME="RZ08811SS-4">4</A> Arhancet GB. Woodard SS. Dietz JD. Garland DJ. Wagner GM. Iyanar K. Collins JT. Blinn JR. Numann RE. Hu X. Huang H.-C. J. Med. Chem. 2010, 53: 4300

<A NAME="RZ08811SS-5A">5a</A> Zhang B.-l. He W. Shi X. Huan M.-l. Huang Q.-j. Zhou S.-y. Bioorg. Med. Chem. Lett. 2010, 20: 805

<A NAME="RZ08811SS-5B">5b</A> Briede J. Daija D. Stivrina M. Duburs G. Cell. Biochem. Funct. 1999, 17: 89

<A NAME="RZ08811SS-5C">5c</A> Klusa V. Drugs Future 1995, 20: 135

<A NAME="RZ08811SS-6">6</A> Evans CG. Jinwal UK. Makley LN. Dickey CA. Gestwicki JE. Chem. Commun. 2011, 47: 529

<A NAME="RZ08811SS-7">7</A> Chang C.-C. Cao S. Kang S. Kai L. Tian X. Pandey P. Dunne SF. Luan C.-H. Surmeier DJ. Silverman RB. Bioorg. Med. Chem. 2010, 18: 3147

<A NAME="RZ08811SS-8A">8a</A> Che J. Lam Y. Synlett 2010, 2415

<A NAME="RZ08811SS-8B">8b</A> Hoffman S. Seayad AM. List B. Angew. Chem. Int. Ed. 2005, 44: 7424

<A NAME="RZ08811SS-8C">8c</A> Rueping M. Suiono E. Azap C. Theissmann T. Bolte M. Org. Lett. 2005, 7: 3781

<A NAME="RZ08811SS-8D">8d</A> Storer RI. Carrera DE. Ni Y. MacMillan DWC. J. Am. Chem. Soc. 2006, 128: 84

<A NAME="RZ08811SS-9">9</A> Hantzsch A. Justus Liebigs Ann. Chem. 1882, 215: 1

<A NAME="RZ08811SS-10A">10a</A> Bridgwood KL. Veitch GE. Ley SV. Org. Lett. 2008, 10: 3627

<A NAME="RZ08811SS-10B">10b</A> Veitch GE. Bridgwood KL. Ley SV. Org. Lett. 2008, 10: 3623

<A NAME="RZ08811SS-10C">10c</A> Veitch GE. Bridgwood KL. Rands-Trevor K. Ley SV. Synlett 2008, 2597

<A NAME="RZ08811SS-11A">11a</A> Sobolev A. Franssen MCR. Vigante B. Cekavicus B. Makarova N. Duburs G. de Groot A. Tetrahedron: Asymmetry 2001, 12: 3251

<A NAME="RZ08811SS-11B">11b</A> Sobolev A. Franssen MCR. Vigante B. Cekavicus B. Zhalubovskis R. Kooijman H. Spek AL. Duburs G. de Groot A. J. Org. Chem. 2002, 67: 401

<A NAME="RZ08811SS-11C">11c</A> Sobolev A. Franssen MCR. Makarova N. Duburs G. de Groot A. Tetrahedron: Asymmetry 2000, 11: 4559

<A NAME="RZ08811SS-11D">11d</A> Boatto G. Nieddu M. Faedda MV. De Caprariis P. Chirality 2003, 15: 494

<A NAME="RZ08811SS-11E">11e</A> de Castro M. Salazar L. Sinisterra J. Tetrahedron: Asymmetry 1997, 8: 857

<A NAME="RZ08811SS-12">12</A> Gianotti M. Martelli G. Spunta G. Campana E. Panunzio M. Mendozza M. Synth. Commun. 2000, 30: 1725