Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2001(16): 2477-2483
DOI: 10.1055/s-2001-18715
DOI: 10.1055/s-2001-18715
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of β-Carbolines from 2-Acyl-1-benzenesulfonyl-3-iodo-1H-indoles
Further Information
Received
13 July 2001
Publication Date:
05 August 2004 (online)
Publication History
Publication Date:
05 August 2004 (online)
Abstract
2-Acyl-1-benzenesulfonyl-3-iodo-1H-indoles and 1-benzenesulfonyl-3-iodo-1H-indole-2-carbaldehyde give in satisfactory yields 1,3- and 3-substituted-β-carbolines, respectively, by combined palladium-catalyzed coupling with alk-1-ynes followed by 6-endo-dig cycloamination reactions.
Key words
indoles - alkynes - 9H-pyrido[3,4-b]indoles - palladium - annulation reactions
-
1a
Braestrup C.Nielsen HM.Petersen EN.Jepsen LH. Biochem. Pharmacol. 1984, 33: 859 -
1b
Lippke KP.Schunack WG.Wenning W.Müller WE. J. Med. Chem. 1983, 26: 499 -
2a
Prinsep MR.Blunt JW.Munro MHG. J. Nat. Prod. 1991, 54: 1068 -
2b
Murata H.Shigemori H.Ishibashi M.Sugama K.Hayashi K.Kobayashi J. Tetrahedron Lett. 1991, 32: 3539 -
2c
Kobayashi J.Cheng J.Ohta T.Nozol S.Ohizumi Y.Sasaki T. J. Org. Chem. 1990, 55: 3666 -
2d
Hagen TJ.Narayanan K.Names J.Cook JM. J. Org. Chem. 1989, 54: 2170 -
2e
Kobayashi J.Nakamura Y.Ohizumi Y.Hirata Y. Tetrahedron Lett. 1986, 27: 1191 - 3
Kardono LB.Angerhofer CK.Tsauri S.Padmawinata K.Pezzuto JM.Kinghorn AD. J. Nat. Prod. 1991, 54: 1360 - 4
Doyle TW.Balitz DM.Grulich RE.Nettleton DE.Gould SJ.Tann C.Moews AE. Tetrahedron Lett. 1981, 22: 4595 -
5a
Love BE. Org. Prep. Proced. Int. 1996, 3 -
5b
Suzuky H.Iwata C.Sakurai K.Tokumoto K.Takahashi H.Hanada M.Yokoyama Y.Murakami Y. Tetrahedron 1997, 53: 1593 -
5c
Choshi T.Matsuya Y.Okita M.Inada K.Sugino E.Hibino S. Tetrahedron Lett. 1998, 39: 2341 -
5d
Sakamoto T.Numata A.Saitoh H.Kondo Y. Chem. Pharm. Bull. 1999, 47: 1740 -
5e
Suzuki H.Unemoto M.Murakemi Y. J. Chem. Soc., Perkin Trans. 1 1999, 1717 -
5f
Choshi T.Kumada T.Fukni M.Matsuya Y.Sugino E.Hibino S. Chem. Pharm. Bull. 2000, 48: 108 - See for example:
-
6a
Arcadi A.Rossi E. Tetrahedron 1998, 54: 15253 -
6b
Arcadi A.Marinelli F.Rossi E. Tetrahedron 1999, 55: 13233 -
6c
Rossi E.Abbiati G.Arcadi A.Marinelli F. Tetrahedron Lett. 2001, 42: 3705 - 7
Arcadi A.Attanasi OA.Guidi B.Rossi E.Santeusanio S. Eur. J. Org. Chem. 1999, 3117 -
8a
Sakamoto T.Kondo Y.Takazama N.Yamanaka H. J. Chem. Soc., Perkin Trans. 1 1996, 1927 -
8b
Saulnier MG.Gribble GW. J. Org. Chem. 1982, 47: 757 -
9a
Choshi T.Sada T.Fujimoto H.Nagayama C.Sugiho E.Hibino S. J. Org. Chem. 1997, 23: 2535 -
9b
Choshi T.Sada T.Fujimoto H.Nagayama C.Sugino E.Hibino S. Tetrahedron Lett. 1996, 37: 2593 - 10
Sakamoto T.Kondo Y.Takazawa N.Yamanaka H. Tetrahedron Lett. 1993, 34: 5955 -
11a
Friour G.Cahiez G.Normant JF. Synthesis 1985, 50 -
11b
Tarbel DS.Leister NA. J. Org. Chem. 1997, 23: 2535 -
12a
Comins DL.Killack MO. J. Org. Chem. 1987, 52: 104 -
12b
Moody CJ.Ward JG. J. Chem. Soc., Perkin Trans. 1 1984, 2903 -
13a
Sonogashira K.Tohda Y.Hagihara N. Tetrahedron Lett. 1975, 50: 4467 -
13b
Rossi R.Carpita A.Bellina F. Org. Prep. Proced. Int. 1995, 127 -
13c
Arcadi A.Attanasi OA.De Crescentini L.Rossi E.Serra-Zanetti F. Tetrahedron 1996, 52: 3997 -
14a
Wan Z.Snyder K. Tetrahedron Lett. 1998, 39: 2487 -
14b
Benson SC.Gross JL.Snyder JK. J. Org. Chem. 1990, 55: 3257 -
14c
Biere H.Russe R.Seelen W. Liebigs Ann. Chem. 1986, 1749 -
14d
Huth A,Rahtz D,Seidelmann D,Schmiechen R,Biere H, andBraestrup CT. inventors; German Patent 3240514. -
15a
Anderson PN.Sharp JN. J. Chem. Soc., Perkin Trans. 1 1980, 1331 -
15b
Sakamoto T.Kondo Y.Miura N.Hayashi K.Yamanaka H. Heterocycles 1986, 24: 2311 -
15c
Sakamoto T.Kondo Y.Yamanaka H. Heterocycles 1988, 27: 2225