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 2013; 45(23): 3295-3299
DOI: 10.1055/s-0033-1339904
DOI: 10.1055/s-0033-1339904
paper
One-Pot Synthesis of Nitriles from Aldehydes Catalyzed by Deep Eutectic Solvent
Further Information
Publication History
Received: 11 July 2013
Accepted after revision: 11 September 2013
Publication Date:
26 September 2013 (online)
Abstract
The choline chloride–urea (1:2) based deep eutectic mixture as an efficient and ecofriendly catalyst for the one-pot synthesis of nitriles from aldehydes under solvent-free conditions under both conventional and microwave irradiation; the products were obtained in good to excellent yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Gu X.-H, Wan XZ, Jiang B. Bioorg. Med. Chem. Lett. 1999; 9: 569
- 1b Chihiro M, Nagamoto H, Tekemura I, Kitano K, Komatsu H, Sekiguchi K, Tabusa F, Mori T, Tominaga M, Yabuuchi Y. J. Med. Chem. 1995; 38: 353
- 1c Jnaneshwara GK, Deshpande VH, Lalithambika M, Ravindranathan T, Bedekar AV. Tetrahedron Lett. 1998; 39: 459
- 1d Wittenberger SJ, Donner BG. J. Org. Chem. 1993; 58: 4139
- 1e Bailey TR, Diana GD, Kowalczyk PJ, Akullian V, Eissenstat MA, Cutcliffe D, Mallamo JP, Carabateas P, Pevear DC. J. Med. Chem. 1992; 35: 4628
- 1f Kadaba PK. Synthesis 1973; 71
- 1g Moody CJ, Doyle KJ. Prog. Heterocycl. Chem. 1997; 9: 1
- 1h Ducept PC, Marsden SP. Synlett 2000; 692
- 2a Larock RC. Comprehensive Organic Transformations . 2nd ed. Wiley-VCH; New York: 1999: 1949-1950, 1955, 1983-1985
- 2b Fleming FF. Nat. Prod. Rep. 1999; 16: 597
- 2c Fleming FF, Yaot L, Ravikumart PC, Funk L, Shook BC. J. Med. Chem. 2010; 53: 7902
- 2d Herr RJ. Bioorg. Med. Chem. 2002; 10: 3379
- 3a The Chemistry of the Cyano Group. Rappoport Z. Interscience; New York: 1970
- 3b Larock RC. Comprehensive Organic Transformations . VCH; New York: 1989
- 3c Kleemann A, Engel J, Kutscher B, Reichert D. Pharmaceutical Substances: Synthesis Patents, Applications . 4th ed. Georg Thieme; Stuttgart: 2001
- 3d Miller JS, Manson JL. Acc. Chem. Res. 2001; 34: 563
- 4 Mowry DT. Chem. Rev. 1948; 42: 189
- 5a Semmelhack MF, Schmid CR. J. Am. Chem. Soc. 1983; 105: 6732
- 5b Chen FE, Kuang YY, Dai HF, Lu L, Huo MA. Synthesis 2003; 2629
- 5c Baxendale IR, Ley SV, Sneddon FH. Synlett 2002; 775
- 5d Wu JD, Chu CM, Yao CF, Shia KS. Chem. Commun. 2007; 301
- 5e Phillips BA, Fodor G, Gal J, Letourneau F, Ryan JJ. Tetrahedron 1973; 29: 3309
- 5f Lee JC, Yoon JM, Baek JW. Bull. Korean Chem. Soc. 2007; 28: 29
- 6 Brackman W, Smith P. Recl. Trav. Chim. Pays–Bas 1963; 82: 757
- 7 Parameswaran KN, Friedman OM. Chem. Ind. (London) 1965; 988
- 8 Bose DS, Narsaiah AV. Tetrahedron Lett. 1998; 39: 6533
- 9 Erman MB, Snow JW, Williams MJ. Tetrahedron Lett. 2000; 41: 6749
- 10 Talukdar S, Hsu J.-L, Chou T.-C, Fang J.-M. Tetrahedron Lett. 2001; 42: 1103
- 11 Bandgar BP, Makone SS. Synth. Commun. 2006; 36: 1347
- 12 Arote ND, Bhalerao DS, Akamanchi KG. Tetrahedron Lett. 2007; 48: 3651
- 13 Telvekar VN, Patel KN, Kundiakar HS, Chaudhari HK. Tetrahedron Lett. 2008; 49: 2213
- 14 Barahman M, Salman S. Tetrahedron Lett. 2005; 46: 6923
- 15 Zhu JL, Lee FY, Wu JD, Kuo CW, Shia KS. Synlett 2007; 1317
- 16a Sharghi H, Sarvari M. Synthesis 2003; 243
- 16b Balaji VR, Kandikere RP. J. Org. Chem. 2012; 77: 5364
- 17 Zhang JL, Chen XR, Xu KL, Huang J. Chem. Res. Chin. Univ. 2011; 27: 712
- 18a Das B, Madhusudhan P, Venkataiah B. Synlett 1999; 1569
- 18b Das B, Ramesh C, Madhusudhan P. Synlett 2000; 1599
- 18c Srinivas KV. N. S, Reddy EB, Das B. Synlett 2002; 625
- 19 Lindberg D, Revenga MF, Widersten M. J. Biotechnol. 2010; 147: 169
- 20 Zheng WR, Xu JL, Huang T, Yang Q, Chen ZC. Res. Chem. Intermed. 2011; 37: 31
- 21 Singh BS, Loba HR, Shankarling GS. Catal. Commun. 2012; 24: 70
- 22 Singh BS, Loba HR, Shankarling GS. Catal. Lett. 2011; 141: 178
- 23a Abbott AP, Boothby D, Capper G, Davies DL, Rasheed R. J. Am. Chem. Soc. 2004; 126: 9142
- 23b Abbott AP, Capper G, Gray S. ChemPhysChem 2006; 7: 803
- 23c Abbott AP, Frisch G, Gurman SJ, Hillman AR, Hartley J, Holyoak F, Ryder KS. Chem. Commun. 2011; 47: 10031
- 23d Abbott AP, Frisch G, Garrett H, Hartley J. Chem. Commun. 2011; 47: 11876
- 24 Patil UB, Kumthekar KR, Nagarkar JM. Tetrahedron Lett. 2012; 53: 3706
- 25 Abbott AP, Capper G, Davies DL, Rasheed RK, Tambyrajah V. Chem. Commun. 2003; 70
- 26a Chattopadhyay K, Dey R, Ranu BC. Tetrahedron Lett. 2009; 48: 3164
- 26b Suzuki Y, Yoshino T, Moriyama K, Togo H. Tetrahedron 2011; 67: 3809
- 26c Millot N, Piazza C, Avolio S, Knochel P. Synthesis 2000; 941
- 26d Yeung PY, Tsang CP, Kwong FY. Tetrahedron Lett. 2011; 52: 7038
- 26e Thomas HG, Greyn HD. Synthesis 1990; 129