Abstract
N-Substituted 4-methyl- and 4-ethylisoquinolone derivatives are
prepared from different N -allylbenzamide
derivatives in a single step through a ligand-free palladium-mediated
intramolecular Heck cyclization.
Key words
isoquinolones - Heck cyclization - intramolecular
cyclization - palladium acetate
References
1
Kametani T.
The Chemistry of the Isoquinoline Alkaloids
Hirokawa & Elsevier;
Tokyo & Amsterdam:
1968.
2
Martin SF.
The Alkaloids
Vol. 31:
Brossi AR.
Academic;
New
York:
1987.
p.252
3
Clark RD.
Souchet M.
Tetrahedron Lett.
1990,
31:
193
4
Mondon A.
Erythria Alkaloids , In Chemistry
of the Alkaloids
Pelletier SW.
Van Nostrand
R.;
New York:
1970.
p.137
5a
Tsuda Y.
Isobe K.
J.
Chem. Soc.
1971,
1555
5b
Stevens RV.
Dupree LE.
Loewenstein PL.
J. Org.
Chem.
1972,
37:
977
6
Whitlock WH.
Smith GL.
J.
Am. Chem. Soc.
1967,
87:
3600
7
Kametani T.
Rukumoto K.
Heterocycles
1975,
3:
931
8
Kametani T.
Kajiwara M.
Takahashi T.
Fukumoto K.
Heterocycles
1975,
3:
179
9
Kametani T.
Hirai Y.
Kajiwara M.
Takahashi T.
Fukumoto K.
Chem.
Pharm. Bull.
1975,
23:
2634
10
Irie H.
Akagi K.
Tani S.
Yabusaki K.
Yamane H.
Chem. Pharm.
Bull.
1973,
21:
855
11
Irie H.
Fukudome J.
Ohmori T.
Tanaka J.
J. Chem. Soc., Chem. Commun.
1975,
63
12
Stork G.
Guthikonda RN.
J. Am. Chem. Soc.
1972,
74:
5109
13
Pettit GR.
Gaddamidi V.
Herald DL.
Cragg GM.
Singh SB.
Schmidt JM.
J. Nat. Prod.
1986,
49:
995
14
Beugelmans R.
Choussy MB.
Synthesis
1981,
729
15
Couture A.
Garandclaudon P.
Synthesis
1986,
576
16
Fisher LE.
Caroon JM.
.
Stabler SR.
Lundberg S.
Muchowski JM.
J. Org. Chem.
1993,
58:
3643
17
Cuevas JC.
Snieckus V.
Tetrahedron Lett.
1989,
30:
5837
18
Kiselyov AS.
Tetrahedron
Lett.
1995,
36:
493
19
Clark R. D.
.
Souchet M.
Kern J. R.
J. Chem. Soc., Chem. Commun.
1989,
930
20
Heck RF.
Palladium Reagents in Organic Synthesis
Academic
Press;
London:
1985.
21a
Heck RF.
Org. React.
1982,
27:
345
21b
Heck RF. In Comprehensive Organic
Synthesis
Trost BM.
Fleming I.
Pergamon;
Oxford:
1991.
p.833
22
Zhang Y.
Negishi E.
J. Am. Chem. Soc.
1989,
111:
3454
23
Trost BM.
Shih S.
J. Am. Chem. Soc.
1993,
115:
12491
24a
Ithle NC.
Heathcock CH.
J. Org. Chem.
1993,
58:
560
24b
Larock RC.
Doty MJ.
Cacchi S.
J. Org. Chem.
1993,
58:
5479
25
Trost BM.
Tanoury GJ.
Lautens M.
Chan C.
McPherson DT.
J.
Am. Chem. Soc.
1994,
116:
4255
26
Hegedus LS.
Angew.
Chem. Int. Ed.
1998,
27:
1113
27
Sakamoto T.
Kondo Y.
Yamanaka H.
Heterocycles
1998,
27:
2225
28
Arcadi A.
Cacchi S.
Marinelli F.
Tetrahedron
Lett.
1989,
30:
2581
29
Tidwell JH.
Senn DR.
Buchwald SL.
J. Am. Chem. Soc.
1991,
113:
4685
30
Larock RC.
Berrios-Pena NG.
Fried CA.
Yum EK.
Leogn CW.
J. Org. Chem.
1993,
58:
4509
31
Liao H.-Y.
Cheng CH.
J. Org. Chem.
1995,
60:
3711
32
Trost BM.
McIntosh MC.
J. Am. Chem. Soc.
1995,
117:
7255
33
Arcadi A.
Cacchi S.
Fabrizi G.
Marinelli F.
Pacc P.
Synlett
1996,
568
34
Negishi E.-I.
Coperet C.
Ma S.
Lion S.-Y.
Lire F.
Chem. Rev.
1996,
96:
365
35a
Cavicchioli M.
Decortiat S.
Bouyssis D.
Gore J.
Bahme G.
Tetrahedron
1996,
52:
11463
35b
Bouyssi D.
Cavicchioli M.
Balme G.
Synlett
1997,
944
36
Larock RC.
Yum EK.
Doty MJ.
Sham KKC.
J. Org.
Chem.
1995,
60:
3270
37
Jeschke T.
Wensbo D.
Annby U.
Gronoaitz S.
Cohen LA.
Tetrahedron
Lett.
1993,
34:
6471
38
Majumdar KC.
Chattopadhaya B.
Taher A.
Synthesis
2007,
3647
39 Majumdar, K. C.; Chattopadhaya, B.;
Nath, S. Tetrahedron Lett ., in press.
40 Majumdar K. C., Debnath P., Taher
A., Pal A. K.; Can. J. Chem ., in press.
41a
Christoph G.
Buchwald SL.
Chem.
Eur. J.
1999,
5:
3107
41b
Bumagin NA.
Bykov VV.
Sukhomlinova LI.
Tolstaya TP.
Beletskaya IP.
J. Organomet.
Chem.
1995,
486:
25