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Synthesis 2010(19): 3346-3352
DOI: 10.1055/s-0030-1257910
DOI: 10.1055/s-0030-1257910
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Novel Furo-, Thieno-, and Pyrroloazepines
Further Information
Received
23 April 2010
Publication Date:
30 July 2010 (online)
Publication History
Publication Date:
30 July 2010 (online)
Abstract
The synthesis of novel furo-, thieno-, and pyrroloazepine compounds, using the oxidative radical alkylation of three five-membered heterocyclic 3-acetic acid derivatives, is described. The bicyclic systems were obtained, via a small number of steps, directly from commercially available materials.
Key words
oxidative radicals - carboxylic acid homologation - furan - thiophene - pyrrole - azepinones
- 1
Martínez R.Clara-Sosa A.Ramírez Apan Ma T. Bioorg. Med. Chem. 2007, 15: 3912 - 2
Martínez R.Ávila JG.Ramírez MaT.Pérez A.Martínez A. Bioorg. Med. Chem. 2006, 14: 4007 -
3a
Lahusen T.De Siervi A.Kunick C.Senderowicz A. Mol. Carcinog. 2003, 36: 183 -
3b
Kunick C.Zeng Z.Gussio R.Zaharevitz D.Leost M.Totzke F.Schaechtele C.Kubbutat MHG.Meijer L.Lemcke T. ChemBioChem 2005, 6: 541 - 4
van Leusen AM.Siderius H.Hoogenboom H.Van Leusen D. Tetrahedron Lett. 1972, 13: 5337 - 5
Bachman WE.Stuve WS. Org. React. 1942, 1: 38 - 6
Furniss BS.Hannaford AJ.Smith PWG.Tatchell AR. Vogel’s Textbook of Practical Organic Chemistry 5th ed.: Longman; Essex: 1989. p.430 - 7
Demopoulos VJ. Synth. Commun. 1989, 19: 2585 - 8
Bray BL.Mathies PH.Naef R.Solas DR.Tidwell TT.Artis DR.Muchowski JM. J. Org. Chem. 1990, 55: 637 - 9
Osornio YM.Cruz-Almanza R.Jiménez-Montaño V.Miranda LD. Chem. Commun. 2003, 2316 - 10
Caddick S.Judd DB.Lewis AK.de K..Reich MT.Williams MRV. Tetrahedron 2003, 59: 5417 - 11
Caddick S.Haynes AK.de K.Judd DB.Williams MRV. Tetrahedron Lett. 2000, 41: 3513 - 12
Reyes-Gutierrez PE.Torres-Ochoa RO.Martínez R.Miranda LD. Org. Biomol. Chem. 2009, 7: 1388 - 13
Newman MS.Beal PF. J. Am. Chem. Soc. 1950, 72: 5163 - 14
Still WC.Khan M.Mitra A. J. Org. Chem. 1978, 43: 2923 - 15
Flitsch W.Pandl K.Ruβkamp P. Liebigs Ann. Chem. 1983, 529 - 16
Shim YK.Youn JI.Chun JS.Park TH.Kim MH.Kim WJ. Synthesis 1990, 753 - 17
Furniss BS.Hannaford AJ.Smith PWG.Tatchell AR. Vogel’s Textbook of Practical Organic Chemistry 5th ed.: Longman; Essex: 1989. p.609 - 18
Ghosh A.Raha CR. Indian Chem. Soc. 1954, 31: 461 - 19
Friedmanh L.Fishel DL.Shechter H. J. Org. Chem. 1965, 30: 1457