Abstract
Dihydroisoquinoline derivatives and their analogues, prepared by the Bischler-Napieralsky
reaction, were converted to their indole-fused derivatives. Scope and limitations
of the palladium-catalyzed reaction, proceeding through the tautomeric enamine forms
of these compounds, were studied and the process was extended to the preparation of
racemic mangochinine.
Key words
ring closure - palladium - catalysis - indoles - natural products
References <A NAME="RZ00806SS-1">1 </A>
Present address: Department of Chemistry, Faculty of Veterinary Sciences, Szent István
University, 1078 Budapest, István u. 2, Hungary.
<A NAME="RZ00806SS-2">2 </A>
Present address: Chinoin Rt., 1045 Budapest, Tó u. 1-5., Hungary.
<A NAME="RZ00806SS-3">3 </A>
Ewing J.
Hughes K.
Ritchie E.
Taylor WC.
Nature
1952,
169:
618
<A NAME="RZ00806SS-4">4 </A>
Moskowitz H.
Leboeuf M.
Care A.
von Angerer A.
Can. J. Chem.
1989,
67:
947
<A NAME="RZ00806SS-5">5 </A>
Qiu S-x.
Liu C.
Zhao S-x.
Xia Z-c.
Farnsworth NR.
Fong HHS.
Tetrahedron Lett.
1998,
39:
4167
<A NAME="RZ00806SS-6">6 </A>
Ambros A.
von Angerer A.
Wiegrebe W.
Arch. Pharm. (Weinheim, Ger.)
1988,
321:
481
<A NAME="RZ00806SS-7">7 </A>
Ambros A.
von Angerer A.
Wiegrebe W.
Arch. Pharm. (Weinheim, Ger.)
1988,
321:
743
<A NAME="RZ00806SS-8">8 </A>
Ewing J.
Hughes GK.
Ritchie E.
Taylor WC.
Aust. J. Chem.
1953,
6:
78
<A NAME="RZ00806SS-9">9 </A>
Robinson R.
Sugasawa S.
J. Chem. Soc.
1932,
789
<A NAME="RZ00806SS-10">10 </A>
Schöpf C.
Thierfelder K.
Justus Liebigs Ann. Chem.
1932,
497:
22
<A NAME="RZ00806SS-11">11 </A>
Kametani T.
Ogasawara K.
J. Chem. Soc.
1967,
2208
<A NAME="RZ00806SS-12">12 </A>
Meyers AI.
Sielecki TM.
Crans DC.
Marshman RW.
Nguyen TH.
J. Am. Chem. Soc.
1992,
114:
8483
<A NAME="RZ00806SS-13">13 </A>
Kano S.
Yokomatsu T.
Shibuya S.
Chem. Pharm. Bull.
1977,
25:
2401
<A NAME="RZ00806SS-14">14 </A>
Kano S.
Yokomatsu T.
Shibuya S.
Chem. Pharm. Bull.
1977,
25:
2875
<A NAME="RZ00806SS-15">15 </A>
Orito K.
Harada R.
Uchiito S.
Tokuda M.
Org. Lett.
2000,
2:
1799
<A NAME="RZ00806SS-16">16 </A>
Padwa A.
Waterson AG.
Tetrahedron
2000,
56:
10159
<A NAME="RZ00806SS-17">17 </A>
Takano S.
Satoh S.
Ogasawara K.
Heterocycles
1987,
26:
1483
<A NAME="RZ00806SS-18">18 </A>
Cammerer SS.
Viciu MS.
Stevens ED.
Nolan SP.
Synlett
2003,
1871
<A NAME="RZ00806SS-19">19 </A>
Stenlake J.
Waigh RD.
Dewar GH.
Hughes R.
Chapple DJ.
Cocker GG.
Eur. J. Med. Chem. Chim. Ther.
1981,
16:
515
<A NAME="RZ00806SS-20">20 </A>
Watanabe A.
Kunitomo J.
Heterocycles
1998,
48:
1623
<A NAME="RZ00806SS-21">21 </A>
Watanabe M.
Yamamoto T.
Nishiyama M.
Angew. Chem. Int. Ed.
2000,
39:
2501
<A NAME="RZ00806SS-22A">22a </A>
Willis MC.
Taylor D.
Gillmore AT.
Org. Lett.
2004,
6:
4755
<A NAME="RZ00806SS-22B">22b </A>
Chen C.-y.
Dormer PG.
J. Org. Chem.
2005,
70:
6964
<A NAME="RZ00806SS-23">23 </A>
Szántay C.
Dörnyei G.
Blaskó G.
Bárczai-Beke M.
Péchy P.
Arch. Pharm. (Weinheim, Ger.)
1981,
314:
983
<A NAME="RZ00806SS-24">24 </A>
Kano S.
Yokomatsu T.
Shibuya S.
Chem. Pharm. Bull.
1975,
23:
1098
<A NAME="RZ00806SS-25A">25a </A>
Diker K.
de Maindrevill M.
Lévy J.
Tetrahedron Lett.
1995,
36:
2497
<A NAME="RZ00806SS-25B">25b </A>
Jackson M.
J. Chem. Soc. C
1966,
2061
<A NAME="RZ00806SS-26">26 </A>
Baker W.
Robinson R.
J. Chem. Soc.
1925,
1424
<A NAME="RZ00806SS-27">27 </A>
Karim MA.
Linnell WH.
Sharp LK.
J. Pharm. Pharmacol.
1960,
12:
82 ; Chem. Abstr. 1960 , 54 , 74420
<A NAME="RZ00806SS-28">28 </A>
Battersby AR.
Southgate R.
Staunton J.
Hirst M.
J. Chem. Soc. C
1966,
1052
<A NAME="RZ00806SS-29">29 </A>
Sargent LJ.
J. Org. Chem.
1961,
26:
1754