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Synthesis 2007(10): 1559-1565
DOI: 10.1055/s-2007-966041
DOI: 10.1055/s-2007-966041
PAPER
© Georg Thieme Verlag Stuttgart · New York
Novel Synthesis of Arylethynyl Heterocycles
Further Information
Received
14 February 2007
Publication Date:
02 May 2007 (online)
Publication History
Publication Date:
02 May 2007 (online)
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Abstract
A new and simple synthesis of 2-arylethynylindole and 2-arylethynylpyrrole is described. N-Deprotection and subsequent base-catalyzed elimination of N-tosylheteroaryl benzyl ketones are the key steps of the process.
Key words
acetylenes - indole - pyrrole - elimination - tosyl protecting group
-
1a
Gribble GW.Fletcher GL.Ketcha D.Rajopadhye M. J. Org. Chem. 1989, 54: 3264 -
1b
Saxton JE. Nat. Prod. Rep. 1993, 10: 349 -
1c
Sundberg RJ.Russell HE. J. Org. Chem. 1973, 38: 3324 - 2
Hodson FM.Madge DJ.Slawin ANZ.Widdowson DA.Williams DJ. Tetrahedron 1994, 50: 1899 -
3a
Tedesco R.Youngman MK.Wilson SR.Katzenellenbogen JA. Bioorg. Med. Chem. Lett. 2001, 11: 1281 -
3b
Stille JK.Labadie JW. J. Am. Chem. Soc. 1983, 105: 6129 - Several procedures have been described for the removal of the protecting group, see:
-
4a
Joule JA. In Science of Synthesis Vol. 10:Thomas EJ. Thieme; Stuttgart: 2000. p.361 -
4b
Bowman RE.Evans DD.Islip PJ. Chem. Ind. 1971, 53: 33 -
5a
Dunne JP.Aiken S.Duckett SB.Konya D.Almeida Leñero KQ.Drent E. J. Am. Chem. Soc. 2004, 126: 16708 -
5b
Kodomari M.Nagaoka T.Furusawa Y. Tetrahedron Lett. 2001, 42: 3105 -
5c
Hendrickson JB.Hussoin MS. Synthesis 1989, 217 -
5d
Trickes G.Braun HP.Meier H. Justus Liebigs Ann. Chem. 1977, 1347 - 6 Several procedures can be found in:
Tyrrell E. Alkynes, In Comprehensive Organic Functional Group Transformations II Vol. 1:Katritzky AR.Richard JK. Elsevier Ltd.; Oxford: 2005. p.1083 -
7a
Banwell M.Flynn B.Hockless D. Chem. Commun. 1997, 2259 -
7b
Hiroya K.Suzuky N.Yasuhara A.Egawa Y.Kasano A.Sakamoto T. J. Chem. Soc., Perkin Trans. 1 2000, 4339 -
7c
Ridley CP.Reddy MVR.Rocha G.Bushman FD.Faulkner DJ. Bioorg. Med. Chem. 2002, 10: 3285 -
7d
Cironi P.Manzanares I.Albericio F.Álvarez M. Org. Lett. 2003, 5: 2959 -
7e
Tardy C.Facompré M.Laine W.Baldeyrou B.García-Grávalos D.Francesch F.Mateo C.Pastor A.Jiménez JA.Manzanares I.Cuevas C.Bailly C. Bioorg. Med. Chem. 2004, 12: 1697 -
7f
Chen Q.-H.Praveen Rao PN.Knaus EE. Bioorg. Med. Chem. 2005, 13: 6425 - 8
Okauchi T.Itonaga M.Minami T.Owa T.Kitoh K.Yoshino H. Org. Lett. 2000, 2: 1485 - 10
Armarego WLF.Chai CLL. In Purification of Laboratory Chemicals 5th ed.: Butterworth-Heinemann (Elsevier); Oxford: 2003.
References
Reverse phase analytical HPLC was performed on a Waters Alliance 2695 separation module using a Waters Xterra MS C18 column (150 × 4.6 mm, 5 µm) and a Waters 996 PDA detector at 254 nm. The solvent system used was: A: TFA-H2O, 0.045%, B: TFA-MeCN, 0.036%. A linear gradient from 50% B to 100% B over 15 minutes was used. The retention times of 1 and 3 were 9.1 and 8.4 min, respectively.