RSS-Feed abonnieren
DOI: 10.1055/s-0030-1258030
Synthesis of Tetrahydropyrrolo[1,2-a]quinoxalines and Tetrahydropyrido[1,2-a]quinoxalines via a One-Pot CuI-Catalyzed Aryl Amination-Hydrolysis-Condensation Process
Publikationsverlauf
Publikationsdatum:
19. August 2010 (online)

Abstract
CuI-catalyzed coupling of 2-halotrifluoroacetanilides with l-proline or pipecolinic acid in DMSO at 90-110 ˚C followed by in situ hydrolysis at 100 ˚C afforded tetrahydropyrrolo[1,2-a]quinoxalines or tetrahydropyrido[1,2-a]quinoxalines.
Key words
catalysis - coupling - heterocycle - quinoxaline - one-pot process
- Supporting Information for this article is available online:
- Supporting Information (PDF)
- 1a
Tanimori S.Nishimura T.Kirihata M. Bioorg. Med. Chem. Lett. 2009, 19: 4119Reference Ris Wihthout Link - 1b
Kher SM.Cai SX.Weber E.Keana JFW. J. Org. Chem. 1995, 60: 5838Reference Ris Wihthout Link - 2
Abusm Shuheil MY.Hassuneh MR.Al-Hiari YM.Qaisi AM.El-Abadelah MM. Heterocycles 2007, 71: 2155 - 3
Abou-Gharbia M.Freed ME.McCaully RJ.Silver PJ.Wendt RL. J. Med. Chem. 1984, 27: 1743 - 4a
Vega MC.Montero-Torres A.Marrero-Ponce Y.Rolón M.Gómez-Barrio A.Escario JA.Arán VJ.Nogal JJ.Meneses-Marcel A.Torrens F. Bioorg. Med. Chem. Lett. 2006, 16: 1898Reference Ris Wihthout Link - 4b
Meneses-Marcel A.Marrero-Ponce Y.Machado-Tugores Y.Montero-Torres A.Pereira DM.Escario JA.Nogal-Ruiz JJ.Ochoa C.Arán VJ.Martínez-Fernández AR.Sánchez RNG. Bioorg. Med. Chem. Lett. 2005, 15: 3838Reference Ris Wihthout Link - 5
Miyashiro J.Woods KW.Park CH.Liu X.Shi Y.Johnson EF.Bouska JJ.Olson AM.Luo Y.Fry EH.Giranda VL.Penning TD. Bioorg. Med. Chem. Lett. 2009, 19: 4050 - 6a
Jamieson C.Congreve MS.Emiabata-Smith DF.Ley SV.Scicinski JJ. Org. Process Res. Dev. 2002, 6: 823Reference Ris Wihthout Link - 6b
Chicharro R.de Castro S.Reino JL.Arán VJ. Eur. J. Org. Chem. 2003, 2314Reference Ris Wihthout Link - 7a
Cai Q.Zou B.Ma D. Angew. Chem. Int. Ed. 2006, 45: 1276Reference Ris Wihthout Link - 7b
Xie X.Chen Y.Ma D. J. Am. Chem. Soc. 2006, 128: 16050Reference Ris Wihthout Link - 7c
Zou B.Yuan Q.Ma D. Angew. Chem. Int. Ed. 2007, 46: 2598Reference Ris Wihthout Link - 7d
Liu F.Ma D. J. Org. Chem. 2007, 72: 4884Reference Ris Wihthout Link - 7e
Chen Y.Xie X.Ma D. J. Org. Chem. 2007, 72: 9329Reference Ris Wihthout Link - 7f
Chen Y.Wang Y.Sun Z.Ma D. Org. Lett. 2008, 10: 625Reference Ris Wihthout Link - 7g
Yuan Q.Ma D. J. Org. Chem. 2008, 73: 5159Reference Ris Wihthout Link - 8a
Ma D.Zhang Y.Yao J.Wu S.Tao F. J. Am. Chem. Soc. 1998, 120: 12459Reference Ris Wihthout Link - 8b
Zhang H.Cai Q.Ma D. J. Org. Chem. 2005, 70: 5164Reference Ris Wihthout Link - For selected examples about heterocycle synthesis based on copper-catalyzed N-arylation, see:
- 10a
Evindar G.Batey RA. Org. Lett. 2003, 5: 133Reference Ris Wihthout Link - 10b
Klapars A.Parris S.Anderson KW.Buchwald SL. J. Am. Chem. Soc. 2004, 126: 3529Reference Ris Wihthout Link - 10c
Yuen J.Fang Y.-Q.Lautens M. Org. Lett. 2006, 8: 653Reference Ris Wihthout Link - 10d
Zheng N.Buchwald SL. Org. Lett. 2007, 9: 4749Reference Ris Wihthout Link - 10e
Yang D.Fu H.Hu L.Jiang Y.Zhao Y. J. Org. Chem. 2008, 73: 7841Reference Ris Wihthout Link - 10f
Kim J.Lee SY.Lee J.Do Y.Chang S. J. Org. Chem. 2008, 73: 9454Reference Ris Wihthout Link - 10g
Liu X.Fu H.Jiang Y.Zhao Y. Angew. Chem. Int. Ed. 2009, 48: 348Reference Ris Wihthout Link - 10h
Wang H.Jiang Y.Gao K.Ma D. Tetrahedron 2009, 65: 8956Reference Ris Wihthout Link - 10i
Reeves JT.Fandrick DR.Tan Z.Song JJ.Lee H.Yee NK.Senanayake CH. J. Org. Chem. 2010, 75: 992Reference Ris Wihthout Link - 10j
Ma D.Geng Q.Zhang H.Jiang Y. Angew. Chem. Int. Ed. 2010, 49: 1291Reference Ris Wihthout Link
References and Notes
General Procedure for the Synthesis of Quinoxaline Derivatives: A Schlenk tube was charged with 2-iodo-trifluoroacetanilide (0.5 mmol), CuI (10 mg, 0.02 mmol), l-proline (or pipecolinic acid) (1.5 mmol), and K2CO3 (1.0 mmol) (for bromide, Cs2CO3 was used). The tube was evacuated and backfilled with argon. DMSO (4 mL) was added into the tube. The reaction mixture was stirred at 90 ˚C (for bromide, 110 ˚C) for 10-24 h. Then H2O (3 mL) was added and the reaction mixture was stirred at 100 ˚C for 8-12 h. After the reaction mixture was cooled, sat. NH4Cl (10 mL) solution was added. The mixture was extracted with EtOAc and the organic layer was washed with H2O, brine and dried over Na2SO4. After concentration in vacuo, the residue was purified by column chromatography on silica gel (eluting with 6:1 → 4:1 PE-EtOAc) to provide the desired product.