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Synthesis 2009(5): 767-774
DOI: 10.1055/s-0028-1083366
DOI: 10.1055/s-0028-1083366
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Facile Synthetic Route towards Substituted Thieno[3,2-e]indoles
Further Information
Received
28 August 2008
Publication Date:
11 February 2009 (online)
Publication History
Publication Date:
11 February 2009 (online)
Abstract
A number of substituted thieno[3,2-e]indoles have been prepared in high yields via a tetrabutylammonium fluoride mediated cyclization of 5-acetamido-4-ethynylbenzothiophenes, which, in turn, are easily accessible from the corresponding 4-iodobenzothiophenes. This method presents a viable alternative to the traditionally used Fischer indolization procedures.
Key words
thienoindoles - palladium - cyclizations - fused-ring systems - tetrabutylammonium fluoride
- 1
Sharma KS.Singh V. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1976, 14: 797 -
2a
Rawal VH.Jones RJ.Cava MP. J. Org. Chem. 1987, 52: 19 -
2b
Antelo B.Castedo L.Delamano J.Gomez A.Lopez C.Tojo G. J. Org. Chem. 1996, 61: 1188 - 3
Rao MVB.Kumar UKS.Ila H.Junjappa H. Tetrahedron 1999, 55: 11563 - 4
Humphrey GR.Kuethe JT. Chem. Rev. 2006, 106: 2875 -
5a
Castro CE.Havlin R.Honwad VK.Malte AM.Moje SW. J. Am. Chem. Soc. 1969, 91: 6464 -
5b
Ezquerra J.Pedregal C.Lamas C.Barluenga J.Pérez M.García-Martín MA.González JM. J. Org. Chem. 1996, 61: 5804 - 6
Hiroya K.Itoh S.Sakamoto T. J. Org. Chem. 2004, 69: 1126 - 7
Koradin C.Dohle W.Rodriguez AL.Schmid B.Knochel P. Tetrahedron 2003, 59: 1571 -
8a
Yasuhara A.Kanamori Y.Kaneko M.Numata A.Kondo Y.Sakamoto T. J. Chem. Soc., Perkin Trans. 1 1999, 529 -
8b
Hiroya K.Jouka R.Kameda M.Yasuhara A.Sakamoto T. Tetrahedron 2001, 57: 9697 - 9
Osuga H.Suzuki H.Tanaka K. Bull. Chem. Soc. Jpn. 1997, 70: 891 - 10
Marson CM.Savy P.Rioja AS.Mahadevan T.Mikol C.Veerupillai A.Nsubuga E.Chahwan A.Joel SP. J. Med. Chem. 2006, 49: 800 - 11
Liu Z.Larock RC. Tetrahedron 2007, 63: 347 - 12
Das B.Thirupathi P. J. Mol. Catal. A: Chem. 2007, 269: 12 -
13a
Hiroya K.Matsumoto S.Sakamoto T. Org. Lett. 2004, 6: 2953 -
13b
Hiroya K.Itoh S.Sakamoto T. Tetrahedron 2005, 61: 10958 - 14
Zhang H.-C.Ye H.Moretto AF.Brumfield KK.Maryanoff BE. Org. Lett. 2000, 2: 89 - 15
Adachi H.Palaniappan KK.Ivanov AA.Bergman N.Gao Z.-G.Jacobson KA. J. Med. Chem. 2007, 50: 1810