Abstract
A condensation-cycloaddition-cross-coupling reaction sequence has been applied to
the synthesis of phenanthridone derivatives. This novel two-step procedure is based
on a three-component reaction to give 2-halobenzamide-substituted cyclohexenes, which
undergo palladium-catalyzed intramolecular Heck cyclizations.
Key words
domino reactions - Heck reactions - isomerizations - heterocycles - palladium
References
For selected reviews on multicomponent and domino reactions, see:
<A NAME="RZ02705SS-1A">1a </A>
Tietze LF.
Haunert F. In
Stimulating Concepts in Chemistry
Shibasaki M.
Stoddart JF.
Vögtle F.
Wiley-VCH;
Weinheim:
2000.
p.39
<A NAME="RZ02705SS-1B">1b </A>
Dömling A.
Ugi I.
Angew. Chem. Int. Ed.
2000,
39:
3168
<A NAME="RZ02705SS-1C">1c </A>
Bienaymé H.
Hulme C.
Oddon G.
Schmitt P.
Chem.-Eur. J.
2000,
6:
3321
<A NAME="RZ02705SS-1D">1d </A>
Multicomponent Reactions
1st ed.:
Zhu J.
Bienaymé H.
Wiley;
New York:
2005.
<A NAME="RZ02705SS-2">2 </A>
Jacobi von Wangelin A.
Neumann H.
Gördes D.
Klaus S.
Strübing D.
Beller M.
Chem. Eur. J.
2003,
9:
4283
<A NAME="RZ02705SS-3A">3a </A>
Beller M.
Eckert M.
Angew. Chem. Int. Ed.
2000,
39:
1010
<A NAME="RZ02705SS-3B">3b </A>
Gördes D.
Neumann H.
Jacobi von Wangelin A.
Fischer C.
Drauz K.
Krimmer H.-P.
Beller M.
Adv. Synth. Catal.
2003,
345:
510
<A NAME="RZ02705SS-3C">3c </A>
Enzmann A.
Eckert M.
Ponikwar W.
Polborn K.
Schneiderbauer S.
Beller M.
Beck W.
Eur. J. Inorg. Chem.
2004,
1330
<A NAME="RZ02705SS-3D">3d </A>
Beller M.
Eckert M.
Vollmüller F.
Bogdanovic S.
Geissler H.
Angew. Chem., Int. Ed. Engl.
1997,
36:
1494
<A NAME="RZ02705SS-4">4 </A>
Gördes D.
Jacobi von Wangelin A.
Klaus S.
Neumann H.
Strübing D.
Hübner S.
Jiao H.
Baumann W.
Beller M.
Org. Biomol. Chem.
2004,
2:
845
<A NAME="RZ02705SS-5A">5a </A>
Neumann H.
Jacobi von Wangelin A.
Gördes D.
Spannenberg A.
Beller M.
J. Am. Chem. Soc.
2001,
123:
8398
<A NAME="RZ02705SS-5B">5b </A>
Jacobi von Wangelin A.
Neumann H.
Gördes D.
Spannenberg A.
Beller M.
Org. Lett.
2001,
3:
2895
<A NAME="RZ02705SS-5C">5c </A>
Neumann H.
Jacobi von Wangelin A.
Gördes D.
Spannenberg A.
Baumann W.
Beller M.
Tetrahedron
2002,
58:
2381
<A NAME="RZ02705SS-6">6 </A>
Neumann H.
Jacobi von Wangelin A.
Gördes D.
Klaus S.
Jiao H.
Spannenberg A.
Beller M.
Krüger T.
Wendler C.
Thurow K.
Stoll N.
Chem. Eur. J.
2003,
9:
2273
<A NAME="RZ02705SS-7">7 </A>
Neumann H.
Jacobi von Wangelin A.
Klaus S.
Strübing D.
Gördes D.
Beller M.
Angew. Chem. Int. Ed.
2003,
42:
4503
<A NAME="RZ02705SS-8">8 </A>
Neumann H.
Klaus S.
Klawonn M.
Strübing D.
Hübner S.
Gördes D.
Jacobi von Wangelin A.
Lalk M.
Beller M.
Z. Naturforsch., B
2004,
59:
431
<A NAME="RZ02705SS-9A">9a </A>
Baldwin JE.
J. Chem. Soc., Chem. Commun.
1976,
18:
734
<A NAME="RZ02705SS-9B">9b </A> For total syntheses featuring intramolecular Heck reactions to fashion cis -decalins, see:
Link JT.
Overman LE. In
Metal-catalyzed Cross-coupling Reactions
Diederich F.
Stang PJ.
Wiley-VCH;
Weinheim:
1998.
p.231
<A NAME="RZ02705SS-10A">10a </A> For a recent ortho -lithiation/Suzuki coupling approach toward Hippadine, see:
Hartung CG.
Fecher A.
Chapell B.
Snieckus V.
Org. Lett.
2003,
5:
1899
<A NAME="RZ02705SS-10B">10b </A> For a Heck-type biaryl synthesis, see:
Garden SJ.
Torres JC.
Pinto AC.
J. Braz. Chem. Soc.
2000,
11:
441
For Heck ring closure procedures toward Lycoricidine, see:
<A NAME="RZ02705SS-11A">11a </A>
Chida N.
Ohtsuka M.
Ogawa S.
Tetrahedron Lett.
1991,
32:
4525
<A NAME="RZ02705SS-11B">11b </A>
Martin SF.
Tso H.-H.
Heterocycles
1993,
35:
85
<A NAME="RZ02705SS-11C">11c </A>
Hudlicky T.
Olivo HF.
J. Am. Chem. Soc.
1992,
114:
9694
<A NAME="RZ02705SS-11D">11d </A>
Hudlicky T.
Olivo HF.
McKibben B.
J. Am. Chem. Soc.
1994,
116:
5108
<A NAME="RZ02705SS-11E">11e </A>
McIntosh MC.
Weinreb SM.
J. Org. Chem.
1993,
58:
4823
<A NAME="RZ02705SS-12">12 </A>
Tan Z.
Negishi E.-I. In
Handbook of Organopalladium Chemistry for Organic Synthesis
Vol. 1:
Negishi E.-I.
Wiley;
New York:
2002.
Chap III.2.18.
<A NAME="RZ02705SS-13">13 </A>
See also Supporting Information of ref. 5a.
<A NAME="RZ02705SS-14">14 </A>
Suitable crystals of 10a were obtained by recrystallization from toluene-EtOAc (10:1).
<A NAME="RZ02705SS-15">15 </A>
X-ray data of 10a were collected with a STOE-IPDS diffractometer using graphite-monochromated Mo-K
α radiation (λ = 0.71069 Å). The structure was solved by direct methods
[16a ]
and refined by full matrix least square techniques against F
²
.
[16b ]
XP (Bruker AXS) was used for structure representation. All non-hydrogen atoms were
refined anisotropically. The hydrogen atoms (except NH) were included at calculated
positions and refined by the riding model. Crystal data for 10a : space group Pna 21 , orthorhombic, a = 13.328 (3), b = 9.314 (2), c = 18.207 (4) Å, V = 2260.2 (9) Å3 , Z = 8, ρcalcd = 1.318 g cm-3 , 11205 reflections measured, 3580 were independent of symmetry and 2524 were observed
[I > 2σ (I )], R 1 = 0.043, wR 2 (all data) = 0.091, 315 parameters.
<A NAME="RZ02705SS-16A">16a </A> SHELXS-86:
Sheldrick GM.
Acta Crystallogr., Sect. A
1990,
46:
467
<A NAME="RZ02705SS-16B">16b </A>
Sheldrick GM.
SHELXL-93
University of Göttingen;
Germany:
1993.