Abstract
A series of 1,4-dihydropyridines were synthesized in an environmentally benign method,
by reacting aldehydes with acetoacetate esters or acetylacetone and ammonium acetate
in refluxing water. The thus formed 1,4-dihydropyridines was subsequently oxidized
in one-pot to the corresponding pyridine derivatives by either ferric chloride or
potassium permanganate.
Key words
1,4-dihydropyridines - pyridines - aromatization - aqueous-phase synthesis
References
<A NAME="RF02305SS-1">1 </A>
Janis RA.
Triggle DJ.
J. Med. Chem.
1983,
26:
775
<A NAME="RF02305SS-2">2 </A>
Böcker RH.
Guengerich FP.
J. Med. Chem.
1986,
29:
1596
<A NAME="RF02305SS-3A">3a </A>
Vanden Eynde J.-J.
Delfosse F.
Mayence A.
Haverbeke YV.
Tetrahedron
1995,
51:
6511
<A NAME="RF02305SS-3B">3b </A>
Alvarez C.
Delgado F.
García O.
Medina S.
Márquez C.
Synth. Commun.
1991,
21:
619
<A NAME="RF02305SS-3C">3c </A>
Delgado F.
Alvarez C.
García O.
Penieres G.
Márquez C.
Synth. Commun.
1991,
21:
2137
<A NAME="RF02305SS-4A">4a </A>
Itoh T.
Nagata K.
Okada M.
Ohsava A.
Tetrahedron Lett.
1995,
36:
2269
<A NAME="RF02305SS-4B">4b </A>
Itoh T.
Nagata K.
Matsuya Y.
Miyazaki M.
Ohsava A.
J. Org. Chem.
1997,
62:
3582
<A NAME="RF02305SS-4C">4c </A>
Zhu X.-Q.
Zhao B.-J.
Cheng J.-P.
J. Org. Chem.
2000,
65:
8158
<A NAME="RF02305SS-5">5 </A>
Ko K.-Y.
Kim J.-Y.
Tetrahedron Lett.
1999,
40:
3207
<A NAME="RF02305SS-6">6 </A>
Sausins A.
Duburs G.
Heterocycles
1988,
27:
291
<A NAME="RF02305SS-7">7 </A>
Vanden Eynde J.-J.
Mayence A.
Maquestiau A.
Tetrahedron
1992,
48:
463
<A NAME="RF02305SS-8A">8a </A>
Zolfigol MA.
Shirini F.
Choghamarani AG.
Mohammadpoor-Baltork I.
Green Chem.
2002,
4:
562
<A NAME="RF02305SS-8B">8b </A>
Zolfigol MA.
Kiany-Borazjani M.
Sadeghi MM.
Mohammadpoor-Baltork I.
Memarian HR.
Synth. Commun.
2000,
30:
3919
<A NAME="RF02305SS-8C">8c </A>
Zolfigol MA.
Kiany-Borazjani M.
Sadeghi MM.
Mohammadpoor-Baltork I.
Memarian HR.
Synth. Commun.
2000,
30:
551
<A NAME="RF02305SS-8D">8d </A>
Zolfigol MA.
Kiany-Borazjani M.
Sadeghi MM.
Memarian HR.
Mohammadpoor-Baltork I.
Synth. Commun.
2000,
30:
2945
<A NAME="RF02305SS-9">9 </A>
Pfister JR.
Synthesis
1990,
689
<A NAME="RF02305SS-10">10 </A>
Maquestiau A.
Mayence A.
Vanden Eynde J.-J.
Tetrahedron Lett.
1991,
32:
3839
<A NAME="RF02305SS-11">11 </A>
Mashraqui SH.
Karnik MA.
Synthesis
1998,
713
<A NAME="RF02305SS-12">12 </A>
Varma RS.
Kumar D.
Tetrahedron Lett.
1999,
40:
21
<A NAME="RF02305SS-13">13 </A>
Mashraqui SH.
Karnik MA.
Tetrahedron Lett.
1998,
39:
4895
<A NAME="RF02305SS-14">14 </A>
Nakamichi N.
Kawashita Y.
Hayashi M.
Synthesis
2004,
1015
<A NAME="RF02305SS-15">15 </A>
Sabitha G.
Reddy GSKK.
Reddy CS.
Fatima N.
Yadav JS.
Synthesis
2003,
1267
<A NAME="RF02305SS-16A">16a </A>
Li CJ.
Chang TH.
Organic Reactions in Aqueous Media
Wiley;
New York:
1997.
<A NAME="RF02305SS-16B">16b </A>
Li CJ.
Chem. Rev.
1993,
93:
2023
<A NAME="RF02305SS-17A">17a </A>
Zhang Z.
Dong Y.-W.
Wang G.-W.
Chem. Lett.
2003,
32:
966
<A NAME="RF02305SS-17B">17b </A>
Wang G.-W.
Zhang Z.
Dong Y.-W.
Org. Process Res. Dev.
2004,
8:
18
<A NAME="RF02305SS-18">18 </A>
Wang, G.-W.; Xia, J.-J.; Miao, C.-B.; Wu, X.-L., submitted.
<A NAME="RF02305SS-19">19 </A>
Balogh M.
Hermecz I.
Mészáros Z.
Laszlo P.
Helv. Chim. Acta
1984,
67:
2270
<A NAME="RF02305SS-20">20 </A>
Khadilkar B.
Borkar S.
Synth. Commun.
1998,
28:
207
<A NAME="RF02305SS-21">21 </A>
Wang B.
Hu Y.
Hu H.
Synth. Commun.
1999,
29:
4193
<A NAME="RF02305SS-22">22 </A>
Vanden Eynde J.-J.
D’Orazio R.
Haverbeke YV.
Tetrahedron
1994,
50:
2479
<A NAME="RF02305SS-23A">23a </A>
Chavan SP.
Kharul RK.
Kalkote UR.
Shivakumar I.
Synth. Commun.
2003,
33:
1333
<A NAME="RF02305SS-23B">23b </A>
Chavan SP.
Dantale SW.
Kalkote UR.
Jyothirmai VS.
Kharul RK.
Synth. Commun.
1998,
28:
2789
<A NAME="RF02305SS-24">24 </A>
Carabateas PM.
Brundáge RP.
Gelotte KO.
Gruett MD.
Lorenz RR.
Opalka CJ.
Singh B.
Thielking WH.
Williams GL.
Lesher G.
J. Heterocycl. Chem.
1984,
21:
1849
<A NAME="RF02305SS-25">25 </A>
Eisner U.
Williams JR.
Matthews BW.
Ziffer H.
Tetrahedron
1970,
26:
899