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 2015; 47(21): 3309-3314
DOI: 10.1055/s-0034-1380448
DOI: 10.1055/s-0034-1380448
paper
Synthesis of Malonates from 3-Halopropynoates, Alcohols, and Water Using DABCO
Further Information
Publication History
Received: 28 March 2015
Accepted after revision: 04 May 2015
Publication Date:
24 July 2015 (online)
Abstract
A new 1,4-diazabicyclo[2.2.2]octane (DABCO) mediated synthesis of malonates from 3-halopropynoates, alcohols, and water is presented. This method proceeds under mild and metal-free conditions, and represents a new straightforward access to 1,3-dicarbonyl compounds.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380448.
- Supporting Information
-
Reference
- 1a Joule JA, Mills K. Heterocyclic Chemistry . 5th ed. Wiley-Blackwell; Oxford: 2010
- 1b Shinkai H, Onogi S, Tanaka M, Shibata T, Iwao M, Wakitani K, Uchida I. J. Med. Chem. 1998; 41: 1927
- 1c Demir AS, Aybey A, Kayalar M. ARKIVOC 2005; (xv): 105 ; http://www.arkat-usa.org/home
- 1d Craig D, Grellepois F. Org. Lett. 2005; 7: 463
- 1e Cui X, Li J, Liu L, Guo Q.-X. Chin. Chem. Lett. 2007; 18: 625
-
1f Deng C.-L, Zou T, Wang Z.-Q, Song R.-J, Li J.-H. J. Org. Chem. 2009; 74: 412
- 1g Liu W.-B, Jiang H.-F, Qiao C.-L. Tetrahedron 2009; 65: 2110
- 1h Hilt G, Weske DF. Chem. Soc. Rev. 2009; 38: 3082
- 1i Perry A, Taylor RJ. K. Chem. Commun. 2009; 3249
- 1j Bonne D, Coquerel Y, Constantieux T, Rodriguez J. Tetrahedron: Asymmetry 2010; 21: 1085
- 1k Zhu F.-L, Wang Y.-H, Zhang D.-Y, Xu J, Hu X.-P. Angew. Chem. Int. Ed. 2014; 53: 10223
- 1l Otera J In Esterification . Wiley-VCH; Weinheim: 2003
- 2a Otera J. Chem. Rev. 1993; 93: 1449
-
2b Enders D, Niemeier O, Henseler A. Chem. Rev. 2007; 107: 5606
- 2c Ishihara K. Tetrahedron 2009; 65: 1085
- 2d Ramalinga K, Vijayalakshmi P, Kaimal TN. B. Tetrahedron Lett. 2002; 43: 879
- 2e Tale RH, Sagar AD, Santan HD, Adude RN. Synlett 2006; 415
- 2f Bose DS, Satyender A, Rudra Das AP, Mereyala HB. Synthesis 2006; 2392
- 2g Hamada M, Miyosh K, Higashino M, Umezawa T, Ohfune Y. Synlett 2010; 2141
- 3a Suzuki T, Matsuki T, Kudo K, Sugita N, Kaishi NK. Synlett 1983; 1483
- 3b Foà M, Francalanci F. J. Mol. Catal. 1987; 41: 89
- 3c Shim SC, Huh KT, Park WH. Synthesis 1987; 59
- 3d Song WH, Jiang XZ. Chin. Chem. Lett. 2000; 11: 1035
- 4a Tuba R, Ungváry F. J. Mol. Catal. A: Chem. 2003; 203: 59
- 4b Tuba R, Fördős E, Ungváry F. J. Mol. Catal. A: Chem. 2005; 236: 113
- 5a Gallucci RR, Jones MJr. J. Org. Chem. 1985; 50: 4404
- 5b Suzuki Y, Katoh H, Ishii Y, Hidai M. J. Mol. Catal. A: Chem. 1995; 95: 129
- 5c Trabelsi H, Szönyi F, Geribaldi S. J. Fluorine Chem. 2001; 107: 177
- 5d Avila-Zárraga JG, Martínez R. Synth. Commun. 2001; 31: 2177
- 6a Yang L.-M, Huang L.-F, Luh T.-Y. Org. Lett. 2004; 6: 1461
- 6b Shi Y, Li X.-Y, Liu J.-H, Jiang W.-F, Sun L.-C. Tetrahedron Lett. 2010; 51: 3626
- 6c Zhang XL, Li PH, Jie Y, Zhang H, Wang L. Synthesis 2011; 2975
- 6d Tang J.-S, Xie Y.-X, Wang Z.-Q, Li J.-H. Synthesis 2011; 2789
- 6e Tang J.-S, Tian M, Sheng W.-B, Guo C.-C. Synthesis 2012; 44: 541
- 6f Wang S.-H, Wang M, Wang L, Wang B, Li PH, Yang J. Tetrahedron 2011; 67: 4800
- 6g Catagnolo D, Botta M. Eur. J. Org. Chem. 2010; 3224
- 6h Zhang M.-M, Gong J, Song R.-J, Li J.-H. Eur. J. Org. Chem. 2014; 6769
- 6i Tang J.-S, Guo C.-C. Synthesis 2015; 47: 108
- 7a Fan M.-J, Yan Z.-Y, Liu W.-M, Liang Y.-M. J. Org. Chem. 2005; 70: 8204
- 7b Kabir MS, Namjoshi OA, Verma R, Lorenz M, Tiruveedhula VV, Monte A, Bertz SH, Schwabacher AW, Cook JM. J. Org. Chem. 2012; 77: 300
- 7c Chen Z.-W, Jiang H.-F, Pan X.-Y, He Z.-J. Tetrahedron 2011; 67: 5920
- 7d Kanemitsu H, Uehara K, Fukuzumi S, Ogo S. J. Am. Chem. Soc. 2008; 130: 17141
For selected reviews and papers, see:
For selected reviews and papers, see:
For selected reviews and papers on the use of alkynyl halides in synthesis, see:
For selected papers, see: