Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2011(7): 1071-1078
DOI: 10.1055/s-0030-1258462
DOI: 10.1055/s-0030-1258462
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
The Use of Magnesium Nitride for the Synthesis of Enantiomerically Pure 1,4-Dihydropyridines via the Hantzsch Reaction
Further Information
Received
3 January 2011
Publication Date:
08 March 2011 (online)
Publication History
Publication Date:
08 March 2011 (online)
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
-
1a
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 -
1b
Dagnino L.Li-Kwong-Ken MC.Wolowyk MW.Wynn H.Triggle CR.Knaus EE. J. Med. Chem. 1986, 29: 2524 -
1c
Dagnino L.Li-Kwong-Ken MC.Wynn H.Wolowyk MW.Triggle CR.Knaus EE. J. Med. Chem. 1987, 30: 640 - 2
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 - 3
Iwanami M.Shibanuma T.Fujimoto M.Kaway R.Tamazawa K.Takenaka T.Takahashi K.Murakami M. Chem. Pharm. Bull. 1979, 27: 1426 - 4
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 -
5a
Zhang B.-l.He W.Shi X.Huan M.-l.Huang Q.-j.Zhou S.-y. Bioorg. Med. Chem. Lett. 2010, 20: 805 -
5b
Briede J.Daija D.Stivrina M.Duburs G. Cell. Biochem. Funct. 1999, 17: 89 -
5c
Klusa V. Drugs Future 1995, 20: 135 - 6
Evans CG.Jinwal UK.Makley LN.Dickey CA.Gestwicki JE. Chem. Commun. 2011, 47: 529 - 7
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 -
8a
Che J.Lam Y. Synlett 2010, 2415 -
8b
Hoffman S.Seayad AM.List B. Angew. Chem. Int. Ed. 2005, 44: 7424 -
8c
Rueping M.Suiono E.Azap C.Theissmann T.Bolte M. Org. Lett. 2005, 7: 3781 -
8d
Storer RI.Carrera DE.Ni Y.MacMillan DWC. J. Am. Chem. Soc. 2006, 128: 84 - 9
Hantzsch A. Justus Liebigs Ann. Chem. 1882, 215: 1 -
10a
Bridgwood KL.Veitch GE.Ley SV. Org. Lett. 2008, 10: 3627 -
10b
Veitch GE.Bridgwood KL.Ley SV. Org. Lett. 2008, 10: 3623 -
10c
Veitch GE.Bridgwood KL.Rands-Trevor K.Ley SV. Synlett 2008, 2597 -
11a
Sobolev A.Franssen MCR.Vigante B.Cekavicus B.Makarova N.Duburs G.de Groot A. Tetrahedron: Asymmetry 2001, 12: 3251 -
11b
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 -
11c
Sobolev A.Franssen MCR.Makarova N.Duburs G.de Groot A. Tetrahedron: Asymmetry 2000, 11: 4559 -
11d
Boatto G.Nieddu M.Faedda MV.De Caprariis P. Chirality 2003, 15: 494 -
11e
de Castro M.Salazar L.Sinisterra J. Tetrahedron: Asymmetry 1997, 8: 857 - 12
Gianotti M.Martelli G.Spunta G.Campana E.Panunzio M.Mendozza M. Synth. Commun. 2000, 30: 1725