Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2012; 44(18): 2919-2925
DOI: 10.1055/s-0032-1316752
DOI: 10.1055/s-0032-1316752
paper
Synthesis of 2,4-Bis(aryloxy)-1,5-diarylpentane-1,5-diones by Base-Mediated Tandem Reaction
Further Information
Publication History
Received: 25 May 2012
Accepted after revision: 26 June 2012
Publication Date:
01 August 2012 (online)
Abstract
A new, practical, base-mediated method has been developed for the synthesis of 2,4-bis(aryloxy)-1,5-diarylpentane-1,5-diones by a tandem α-methylenation–Michael reaction through activation of two C–Cl bonds. This method permits the use of dichloromethane instead of dibromomethane as a source of one carbon atom for the α-methylenation reaction. The products are useful in syntheses of polysubstituted pyridines and methylenebisbenzofurans.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
Reference
- 1a Kleinman EF In Comprehensive Organic Synthesis . Vol. 2. Trost BM, Fleming I. Pergamon; Oxford: 1991: 893
- 1b Shono T, Nishiguchi I, Komamura T, Sasaki M. J. Am. Chem. Soc. 1979; 101: 984
- 1c Huet F, Pellet M, Conia JM. Tetrahedron Lett. 1977; 3505
- 1d Holy NL, Wang YF. J. Am. Chem. Soc. 1977; 99, 944
- 1e Ksander GM, McMurry JE, Johnson M. J. Org. Chem. 1977; 42: 1180
- 1f Danishefsky S, Kitahara T, McKee R, Schuda PF. J. Am. Chem. Soc. 1976; 98: 6715
- 1g Grieco PA. Synthesis 1975; 67
- 1h Tramontini M. Synthesis 1973; 703
- 1i Lee K.-H, Huang E.-S, Piantadosi C, Pagano JS, Geissmann TA. Cancer Res. 1971; 31: 1649
- 1j Kupchan SM, Eakin MA, Thomas AM. J. Med. Chem. 1971; 14: 1147
- 2a Andrisano R, Angeloni AS, De Maria P, Tramontini M. J. Chem. Soc. C 1967; 2307
- 2b Farberov MI, Mironov GS. Dokl. Akad. Nauk SSSR 1963; 148: 1095 ; Chem. Abstr. 1963, 59, 5062
- 2c Ahond A, Cave A, Kan-Fan C, Potier P. Bull. Soc. Chim. Fr. 1970; 2707
- 2d Holy NL, Wang YF. J. Am. Chem. Soc. 1977; 99: 944
- 2e Horák V, Michl J, Zuman P. Tetrahedron Lett. 1961; 744
- 2f Angeloni AS, Angiolini L, De Maria P, Fini A. J. Chem. Soc. C 1968; 2295
- 2g Johnson WS, Szmuszkovicz J, Rogier ER, Hadler HI, Wynberg H. J. Am. Chem. Soc. 1956; 78: 6285
- 3a Hon Y.-S, Hsu T.-R, Chen C.-Y, Lin Y.-H, Chang F.-J, Hsieh C.-H, Szua P.-H. Tetrahedron 2003; 59: 1509
- 3b Chang F.-J, Lu L, Lin W.-C. Tetrahedron 1998; 54: 5233
- 3c Hon Y.-S, Lin W.-C. Tetrahedron Lett. 1995; 36: 7693
- 3d Hon Y.-S, Chang F.-J, Lu L. J. Chem. Soc., Chem. Commun. 1994; 2041
- 4a Riofski MV, John JP, Zheng MM, Kirshner J, Colby DA. J. Org. Chem. 2011; 76: 3676
- 4b Jin Y.-H, Fang F, Zhang X, Liu Q.-Z, Wang H.-B, Tian S.-K. J. Org. Chem. 2011; 76: 4163
- 4c Erkkilä A, Pihko PM. J. Org. Chem. 2006; 71: 2538
- 5a Aguilar D, Contel M, Urriolabeitia EP. Chem.–Eur. J. 2010; 16: 9287
- 5b Xiang X, Shen Q.-S, Wang J.-L, Zhu Z.-Y, Huang W, Zhou X.-G. Organometallics 2008; 27: 1959
- 5c Tsai C.-C, Hsieh I.-L, Cheng T.-T, Tsai PK, Lin K.-W, Yan T.-H. Org. Lett. 2006; 8: 2261
- 5d Yan T.-H, Tsai Chien C.-T, Cho C.-C, Huang P.-C. Org. Lett. 2004; 6: 4961
- 5e Hunt Jr C, Fronczek FR, Billodeaux DR, Stanley GG. Inorg. Chem. 2001; 40: 5192
- 5f Brunet J.-J, Couillens X, Daran JC, Diallo O, Lepetit C, Neibecker D. Eur. J. Inorg. Chem. 1998; 349
- 5g Suisse P, Pellegrini S, Castanet Y, Mortreux A, Lecoulier S. J. Chem. Soc., Chem. Commun. 1995; 847
- 5h Rondon D, Delbeau J, He X.-D, Sabo-Etienne S, Chaudret B. J. Chem. Soc., Dalton Trans. 1994; 1895
- 5i Suzuki H, Kakigano T, Igarashi M, Tanaka M, Moro-oka Y. J. Chem. Soc., Chem. Commun. 1991; 283
- 5j Marder TB, Fultz WC, Calabrese JC, Harlow RL, Milstein D. J. Chem. Soc., Chem. Commun. 1987; 1543
- 5k Jandik P, Schubert U, Schmidbaur H. Angew. Chem., Int. Ed. Engl. 1982; 21: 73
- 6a Li H.-J, He Z.-H, Guo X.-WLi W.-J, Zhao X.-H, Li Z.-P. Org. Lett. 2009; 11: 4176
- 6b Lecomte V, Bolm C. Adv. Synth. Catal. 2005; 347: 1666
- 6c Karvembu R, Natarajan K. Polyhedron 2002; 21: 219
- 6d Maruyama K, Kubo K, Toda Y, Kawase K, Mashino T, Nishinaga A. Tetrahedron Lett. 1995; 36: 5609
- 6e Wilson BD. J. Org. Chem. 1962; 28: 314
- 6f Martin DF, Shamma M, Fernelius WC. J. Am. Chem. Soc. 1958; 80: 5851
- 7a Chilin A, Conconi MT, Marzaro G, Guiotto A, Urbani L, Tonus F, Parnigotto P. J. Med. Chem. 2010; 53: 1862
- 7b Icli M, Pamuk M, Algi F, Onal AM, Cihaner A. Chem. Mater. 2010; 22: 4034
- 7c Grenier CR. G, George SJ, Joncheray TJ, Meijer EW, Reynolds JR. J. Am. Chem. Soc. 2007; 129: 10694
- 8a Zhou L, Shi Y, Xiao Q, Liu Y.-Z, Ye F, Zhang Y, Wang JB. Org. Lett. 2011; 13: 968
- 8b Auzias M, Häussinger D, Neuburger M, Wegner HA. Org. Lett. 2011; 13: 474
- 8c Maimone TJ, Buchwald SL. J. Am. Chem. Soc. 2010; 132: 9990
- 8d Guo X.-W, Yu R, Li H.-J, Li Z.-P. J. Am. Chem. Soc. 2009; 131: 17387
- 9 The configuration of products 2 was unambiguously assigned by means of an X-ray single-crystal diffraction analysis of product 2k. See the Supporting Information for detailed data.
For selected papers on other methods, see:
For transition-metal-catalyzed activation of the both C–Cl bonds in CH2Cl2, see: