Abstract
Within we report a general one-pot high-yielding Friedel-Crafts acylation of indole using acid chlorides and diethylaluminum chloride in gram scale quantities. This general synthesis affords products that are easily isolated and require no complex purification procedures.
Key words
indole - regioselectivity - Friedel-Crafts reactions - acylations
References 1 Wynne, J. H.; Jones-Meehan, J. US Naval Research Laboratory, Washington, D. C., 2004 , unpublished work.
2 Ottoni O.
Neder A. deVF.
Dias AKB.
Cruz RPA.
Aquino LB.
Org. Lett.
2001,
3:
1005
3 Keasling HH.
Willette RE.
Szmuszkoviez J.
J. Med. Chem.
1964,
7:
94
4 Gribble GW.
In Rodd’s Chemistry of Carbon Compounds
2nd ed.:
Sainsbury M.
Elsevier;
Amsterdam:
1997.
p.69
5 Silvestri R.
De Martino G.
La Regina G.
Artico M.
Massa S.
Vargiu L.
Mura M.
Loi AG.
Marceddu T.
La Colla P.
J. Med. Chem.
2003,
46:
2482
6 Pais GCG.
Zhang X.
Marchand C.
Neamati N.
Cowansage K.
Svarovskaia ES.
Pathak VK.
Tang Y.
Nicklaus M.
Pommier Y.
Burke T.
J. Med. Chem.
2002,
45:
3184
7 Jiang X.-H.
Song L.-D.
Long Y.-Q.
J. Org. Chem.
2003,
68:
7555
8 Nicolaou I.
Demopoulos VJ.
J. Med. Chem.
2003,
46:
417
9 Thomas CJ.
Wolak MA.
Birge RR.
Lees WJ.
J. Org. Chem.
2001,
66:
1914
10 Li W.-T.
Hwang D.-R.
Chen C.-P.
Shen C.-W.
Huang C.-L.
Chen T.-W.
Lin C.-H.
Chang Y.-L.
Chang Y.-Y.
Lo Y.-K.
Tseng H.-Y.
Lin C.-C.
Song J.-S.
Chen H.-C.
Chen S.-J.
Wu S.-H.
Chen C.-T.
J. Med. Chem.
2003,
46:
1706
11 Sundberg RJ.
Indoles
Academic Press;
New York:
1996.
Chap. 11.
p.105-118 ; and references cited therein
12 Bergman J.
Venemalm L.
Tetrahedron Lett.
1987,
28:
3741
13 Ketcha DM.
Gribble GW.
J. Org. Chem.
1985,
50:
5451
14 Powers JC.
J. Org. Chem.
1965,
30:
2534
15 Pindur U.
Flo C.
Akgun E.
Tunali M.
Liebigs Ann. Chem.
1986,
1621
16 Bergman J.
Backvall J.-E.
Lindstrom J.-O.
Tetrahedron
1973,
29:
971
17 Wynne JH.
Stalick WM.
J. Org. Chem.
2002,
67:
5850
18 Gribble GW.
Conway SC.
Heterocycles
1990,
30:
627
19 Bennasar ML.
Roca T.
Griera R.
Bassa M.
Bosch J.
J. Org. Chem.
2002,
67:
6268
20 Bennasar M.-L.
Roca T.
Padulles A.
Org. Lett.
2003,
5:
569
21 Battistuzzi G.
Cacchi S.
Fabrizi G.
Marinelli F.
Parisi LM.
Org. Lett.
2002,
4:
1355
22 Yeung KS.
Farkas ME.
Qiu Z.
Yang Z.
Tetrahedron Lett.
2002,
43:
5793
23 Katritzky AR.
Suzuki K.
Singh SK.
He H.-Y.
J. Org. Chem.
2003,
68:
5720
24 Okauchi T.
Itonaga M.
Minami T.
Owa T.
Kitoh K.
Yoshino H.
Org. Lett.
2000,
2:
1485
25 Anthony W.
J. Org. Chem.
1960,
25:
2049
26 Schore N.
Turro N.
J. Am. Chem. Soc.
1975,
97:
2488
27 Ito Y.
Kobayashi K.
Saegusa T.
J. Org. Chem.
1979,
44:
2030
28 Szmuszkovicz J.
J. Org. Chem.
1962,
27:
515
29 Yang CX.
Patel HH.
Ku YY.
Shah R.
Sawick D.
Synth. Commun.
1997,
27:
2125
30 Szmuszkovicz J.
J. Org. Chem.
1962,
27:
1582
31 Biswas K.
Jackson A.
Tetrahedron
1969,
25:
227
32 1 H NMR correlates with that reported: Sawada K.
Okada S.
Kuroda A.
Watanabe S.
Sawada Y.
Tanaka H.
Chem. Pharm. Bull.
2001,
49:
799
33 Buu-Hoi N.
Hoan N.
Recl. Trav. Chim. Pays-Bas
1949,
68:
5
34 Sainsbury M.
Schinazi R.
J. Chem. Soc., Perkin Trans.
1976,
1155
35 Bergman J.
Koch D.
Heterocycl. Commun.
1996,
2:
305
36 Cipiciani A.
Clementi S.
Linda P.
Savelli G.
Sebastiani GV.
Tetrahedron
1976,
32:
2595
