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Synthesis 2006(12): 2019-2030
DOI: 10.1055/s-2006-942393
DOI: 10.1055/s-2006-942393
PAPER
© Georg Thieme Verlag Stuttgart · New York
A New Approach to the Synthesis of Highly Substituted 3-Pyrrolin-2-ones
Further Information
Received
19 January 2006
Publication Date:
11 May 2006 (online)
Publication History
Publication Date:
11 May 2006 (online)
Abstract
The base-promoted cyclization of internal N-propargylmalonamides in the presence of carbonate bases at room temperature or at 80 °C affords highly substituted 3-pyrrolin-2-ones in good yields.
Key words
cyclizations - 3-pyrrolin-2-ones - lactams - propargylamines - palladium
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Ikeguky SM.Sawaki M.Yoshii H.Maeda K.Morishima Y. J. Pestic. Sci. 2000, 25: 107 - 2
Saudi MNS.El Semary MMA.El Sawaf G. Pharmazie 2002, 57: 519 - 3
Kakeya H.Onozawa C.Sato M.Arai K.Osada H. J. Med. Chem. 1997, 40: 391 - 4
Bosch J.Roca T.Catena JL.Llorens O.Perez JJ.Lagunas C.Fernandez AG.Miquel I.Fernandez-Serrat A.Farrerons C. Bioorg. Med. Chem. Lett. 2000, 10: 1745 - 5
Nagao Y.Sano S.Morimoto K.Kakegawa H.Takatani T.Shiro M.Katunuma N. Tetrahedron Lett. 2000, 41: 2419 -
6a
Green MP.Prodger JC.Hayes CJ. Tetrahedron Lett. 2002, 43: 2649 -
6b
Uno H.Baldwin JE.Russell AT. J. Am. Chem. Soc. 1994, 116: 2139 - 7
Meyers AI.Snyder L. J. Org. Chem. 1993, 58: 36 - 8
Brower JO.Lightner AF.McDonagh AF. Tetrahedron 2001, 57: 7813 - 9
Beck B.Picard A.Herdtweck E.Dömling A. Org. Lett. 2004, 6: 39 - 10
Nair V.Mathen JS.Viji S.Srinivas R.Nandakumar MV.Varma L. Tetrahedron 2002, 58: 8113 - 11
Yavari I.Bayat M. Synth. Commun. 2002, 32: 2527 - 12
Grison C.Genève S.Coutrot P. Tetrahedron Lett. 2001, 42: 3831 -
13a
Ghelfi F.Stevens CV.Laureyn I.Van Meenen E.Rogge TM.De Buyck L.Nikitin KV.Grandi R.Libertini E.Pagnoni UM.Schenetti L. Tetrahedron 2003, 59: 1147 -
13b
Bellesia F.De Buyck L.Colucci MV.Ghelfi F.Laureyn I.Libertini E.Mucci A.Pagnoni UM.Pinetti A.Rogge TM.Stevens CV. Tetrahedron Lett. 2001, 42: 4573 - 14
Kang SK.Kim KJ.Yu CM.Hwang JW.Do YK. Org. Lett. 2001, 3: 2851 - 15
Naitoh R.Nakamura Y.Katano E.Nakamura Y.Okada E.Asaoka M. Heterocycles 2004, 63: 1009 - 16
Bouillon JP.Tinant B.Nuzillard JM.Portella C. Synthesis 2004, 711 - 17
Pal M.Swamy NK.Hameed PS.Padakanti S.Yeleswarapu KR. Tetrahedron 2004, 60: 3987 - 18
Tsolomiti G.Tsolomitis A. Tetrahedron Lett. 2004, 45: 9353 - 19
Snider BB.Neubert BJ. J. Org. Chem. 2004, 69: 8952 - 20
Verniest G.Boterberg S.Bombeke F.Stevens CV.De Kimpe N. Synlett 2004, 1059 - 21
Arcadi A.Bianchi G.Marinelli F. Synthesis 2004, 610 - 22
Arcadi A.Cacchi S.Fabrizi G.Marinelli F. Synlett 1993, 65 - 23
Arcadi A.Marinelli F.Pini E.Rossi E. Tetrahedron Lett. 1996, 37: 3387 - 24
Arcadi A.Cacchi S.Fabrizi G.Manna F.Pace P. Synlett 1998, 446 - 25
Arcadi A.Inesi A.Marinelli F.Rossi L.Verdecchia M. Synlett 2005, 67 - 26
Sonogashira K. In Handbook of Organopalladium Chemistry for Organic Synthesis. Palladium-Catalyzed Alkynylation Vol. 1:Negishi E.de Meijere A. Wiley; New York: 2002. p.493-529 - 28
Imada Y.Yuasa M.Nakamura I.Murahashi S. J. Org. Chem. 1994, 59: 2282 -
29a
Geri R.Polizzi C.Lardicci L.Caporusso AM. Gazz. Chim. Ital. 1994, 124: 241 -
29b
Caporusso AM.Geri R.Polizzi C.Lardicci L. Tetrahedron Lett. 1991, 32: 7471
References
For example, when the amide 3a obtained from the reaction of 1a with ethyl malonyl chloride was reacted with 3-iodo-benzotrifluoride in Et3N-DMF at 50 °C for 5 h, in the presence of PdCl2(PPh3)2, 4aa was obtained in 42% yield.
30PdCl2 (PPh3)2 can be used as catalyst with similar results.
31Carried out using piperidine in place of Et3N, with 0.04 equiv of Cul.