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 2016; 48(02): 231-237
DOI: 10.1055/s-0035-1560832
DOI: 10.1055/s-0035-1560832
paper
Phosphorous Acid Promoted Hydration–Condensation of Aromatic Alkynes with Aldehydes Affording Chalcones in an Oil/Water Two-Phase System
Further Information
Publication History
Received: 20 August 2015
Accepted after revision: 07 October 2015
Publication Date:
06 November 2015 (online)
Abstract
A simple and environmentally benign method was developed for the synthesis of chalcones in high to excellent yields by a phosphorous acid promoted alkyne–aldehyde hydration–condensation in an oil/water two-phase system. The method is the first efficient protocol for the preparation of chalcones that is mediated by a simple Brønsted acid in a two-phase system.
Key words
phosphorous acids - two-phase systems - chalcones - hydration - condensation - green chemistrySupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560832.
- Supporting Information
-
References
- 1a Nowakowska Z. Eur. J. Med. Chem. 2007; 42: 125
- 1b Dimmock JR, Elias DW, Beazely MA, Kandepu NM. Curr. Med. Chem. 1999; 6: 1125
- 1c Sahu NK, Balbhadra SS, Choudhary J, Kohli DV. Curr. Med. Chem. 2012; 19: 209
- 1d Bukhari SN. A, Jantan I, Jasamai M. Mini-Rev. Med. Chem. 2013; 13: 87
- 1e Repanas A, Katsori AM, Hadjipavlou-Litina D. Mini-Rev. Med. Chem. 2013; 13: 952
- 1f Kumar D, Kumar M, Kumar A, Singh SK. Mini-Rev. Med. Chem. 2013; 13: 2116
- 1g Xie Y, Yang W, Tang F, Chen X, Ren L. Curr. Med. Chem. 2015; 22: 132
- 2a Pandeya SN, Sriram D, Nath G, De Clercq E. Eur. J. Pharm. Sci. 1999; 9: 25
- 2b Kucerova-Chlupacova M, Kunes J, Buchta V, Vejsova M, Opletalova V. Molecules 2015; 20: 1104
- 2c Mobinikhaledi A, Kalhor M, Jamalifar H. Med. Chem. Res. 2012; 21: 1811
- 3a Liu M, Wilairat M, Go M.-L. J. Med. Chem. 2001; 44: 4443
- 3b Domínguez JN, Charris JE, Lobo G, Gamboa de Domínguez N, Moreno MM, Riggione F, Sanchez E, Olson J, Rosenthal PJ. Eur. J. Med. Chem. 2001; 36: 555
- 3c Ram VJ, Saxena AS, Srivastava S, Chandra S. Bioorg. Med. Chem. Lett. 2000; 10: 2159
- 4a Go ML, Wu X, Liu XL. Curr. Med. Chem. 2005; 12: 483
- 4b Mazzone G, Malaj N, Galano A, Russo N, Toscano M. RSC Adv. 2015; 5: 565
- 5a Wegener JW, Nawrath H. Eur. J. Pharmacol. 1997; 326: 37
- 5b Fang Q, Zhao L, Wang Y, Zhang Y, Li Z, Pan Y, Kanchana K, Wang J, Tong C, Li D, Liang G. Toxicol. Appl. Pharmacol. 2015; 282: 129
- 6a Xia Y, Yang ZY, Xia P, Bastow KF, Nakanishi Y, Lee KH. Bioorg. Med. Chem. Lett. 2000; 10: 699
- 6b Konieczny MT, Konieczny W, Sabisz M, Skladanowski A, Wakieć R, Augustynowicz-Kopeć E, Zwolska Z. Eur. J. Med. Chem. 2007; 42: 729
- 6c Kumar D, Kumar NM, Akamatsu K, Kusaka E, Harada H, Ito T. Bioorg. Med. Chem. Lett. 2010; 20: 3916
- 6d Karthikeyan C, Moorthy NS. H. N, Ramasamy S, Vanam U, Manivannan E, Karunagaran D, Trivedi P. Recent Pat. Anti-Cancer Drug Discovery 2015; 10: 97
- 7a Satyanarayana M, Tiwari P, Tripathi BK, Srivastava AK, Pratap R. Bioorg. Med. Chem. 2004; 12: 883
- 7b Kamal A, Kumar GB, Vishnuvardhan MV. P. S, Shaik AB, Reddy VS, Mahesh R, Bin Sayeeda I, Kapure JS. Org. Biomol. Chem. 2015; 13: 3963
- 8a Veitch NC, Grayer RJ. Nat. Prod. Rep. 2008; 25: 555
- 8b Raimondi L, Benaglia M. Eur. J. Org. Chem. 2001; 1033
- 8c Bukhari SN. A, Jasamai M, Jantan I, Ahmad W. Mini-Rev. Org. Chem. 2013; 10: 73
- 9a Wei Y, Yoshikai N. J. Am. Chem. Soc. 2013; 135: 3756
- 9b Marzinik AL, Felder ER. J. Org. Chem. 1998; 63: 723
- 9c Mishra S, Monir K, Mitra S, Hajra A. Org. Lett. 2014; 16: 6084
- 9d Cho H, Török F, Török B. Green Chem. 2014; 16: 3623
- 9e Xiao X, Mei H, Chen Q, Zhao X, Lin L, Liu X, Feng X. Chem. Commun. 2015; 51: 580
- 9f Wani MY, Bhat AR, Azam A, Lee DH, Choi I, Athar F. Eur. J. Med. Chem. 2012; 54: 845
- 9g Singh UP, Pathak M, Dubey V, Bhat HR, Gahtori P, Singh RK. Chem. Biol. Drug Des. 2012; 80: 572
- 10a Smit FJ, van Biljon RA, Birkholtz L.-M, N’Da DD. Eur. J. Med. Chem. 2015; 90: 33
- 10b Herencia F, Ferrándiz ML, Ubeda A, Dominguez JN, Charris JE, Lobo GM, Alcaraz MJ. Bioorg. Med. Chem. Lett. 1998; 8: 1169
- 10c Ducki S, Forrest R, Hadfield JA, Kendall A, Lawrence NJ, McGown AT, Rennison D. Bioorg. Med. Chem. Lett. 1998; 8: 1051
- 10d Ren J.-L, Zhang X.-Y, Yu B, Wang X.-X, Shao K.-P, Zhu X.-G, Liu H.-M. Eur. J. Med. Chem. 2015; 93: 321
- 10e Lin YM, Zhou Y, Flavin MT, Zhou LM, Nie W, Chen FC. Bioorg. Med. Chem. 2002; 10: 2795
- 10f Jahng Y, Zhao LX, Moon YS, Basnet A, Kim E.-k, Chang HW, Ju HK, Jeong TC, Lee E.-S. Bioorg. Med. Chem. Lett. 2004; 14: 2559
- 10g Alcantara AR, Marinas JM, Sinisterra JV. Tetrahedron Lett. 1987; 28: 1515
- 10h Özdemir A, Altintop MD, Turan-Zitouni G, Çiftçi GA, Ertorun I, Alataş Ö, Kaplancıklı ZA. Eur. J. Med. Chem. 2015; 89: 304
- 10i Julio MA, Sylvia PD, Josefina SF, Francisco DV, Rivero IA. Bioorg. Med. Chem. Lett. 2009; 17: 6780
- 11a Müller TJ. J, Ansorge M, Aktah D. Angew. Chem. Int. Ed. 2000; 39: 1253
- 11b Braun RU, Ansorge M, Müller TJ. J. Chem. Eur. J. 2006; 12: 9081
- 11c Wu X.-F, Neumann H, Beller M. Angew. Chem. Int. Ed. 2010; 49: 5284
- 11d Wu X.-F, Neumann H, Spannenberg A, Schulz T, Jiao H, Beller M. J. Am. Chem. Soc. 2010; 132: 14596
- 11e Hermange P, Gøgsig TM, Lindhardt AT, Taaning RH, Skrydstrup T. Org. Lett. 2011; 13: 2444
- 11f Shang Y, Jie X, Zhou J, Hu P, Huang S, Su W. Angew. Chem. Int. Ed. 2013; 52: 1299
- 11g Zhou J, Wu G, Zhang M, Jie X, Su W. Chem. Eur. J. 2012; 18: 8032
- 11h Yu S, Li X. Org. Lett. 2014; 16: 1220
- 11i Al-Masum M, Ng E, Wai MC. Tetrahedron Lett. 2011; 52: 1008
- 12a Iranpoor N, Kazemi F. Tetrahedron 1998; 54: 9475
- 12b Narender T, Reddy KP. Tetrahedron Lett. 2007; 48: 3177
- 13a Li J, Feng J, Li M, Wang Q, Su Y, Jia Z. Solid State Sci. 2013; 21: 1
- 13b Formentín P, García H, Leyva A. J. Mol. Catal. A: Chem. 2004; 214: 137
- 13c Kantam ML, Prakash BV, Reddy CV. Synth. Commun. 2005; 35: 1971
- 13d Dong F, Jian C, Fei Z, Kai G, Liu Z. Catal. Commun. 2008; 9: 1924
- 13e Kunde LB, Gade SM, Kalyani VS, Gupte SP. Catal. Commun. 2009; 10: 1881
- 13f Krishnakumar B, Velmurugan R, Swaminathan M. Catal. Commun. 2011; 12: 375
- 13g Janaki P, Sekar KG, Thirunarayanan G. Org. Chem.: Indian J. 2013; 9: 68
- 13h Yadav JS, Subba Reddy BV, Vishnumurthy P. Tetrahedron Lett. 2008; 49: 4498
- 13i Rueping M, Bootwicha T, Baars H, Sugiono E. Beilstein J. Org. Chem. 2011; 7: 1680
- 14a Xu Q, Yang ZG, Yin DL, Zhang F. Catal. Commun. 2008; 9: 1579
- 14b Climent MJ, Corma A, Iborra S, Velty A. J. Catal. 2004; 221: 474
- 14c Hargrove-Leak SC, Amiridis MD. Catal. Commun. 2002; 3: 557
- 15 van Leeuwen PW. N. M. Homogeneous Catalysis: Understanding the Art . Kluwer Academic Publishers; Dordrecht: 2004
- 16 Corma A, Garcia H. Chem. Rev. 2003; 103: 4307
- 17a Baba T, Kizuka H, Handa H, Ono Y. Appl. Catal., A 2000; 194–195: 203
- 17b Curini M, Epifano F, Maltese F, Rosati O. Synlett 2003; 552
- 17c Katsukiyo M, Kiyomi Y, Ayo Y, Keisuke I, Hidenori K, Junji I, Akira H. Chem. Lett. 2010; 39: 766
- 17d Saito A, Umakoshi M, Yagyu N, Hanzawa Y. Org. Lett. 2008; 10: 1783
- 17e Masuyama Y, Takamura W, Suzuki N. Eur. J. Org. Chem. 2013; 8033
- 17f Ishikawa T, Mizuta T, Hagiwara K, Aikawa T, Kudo T, Saito S. J. Org. Chem. 2003; 68: 3702
- 17g Jia H.-P, Dreyer DR, Bielawski CW. Adv. Synth. Catal. 2011; 353: 528
- 18a Dhar DN. The Chemistry of Chalcones and Related Compounds . Wiley-Interscience; New York: 1981
- 18b Miquel JF. Bull. Soc. Chim. Fr. 1961; 1369
- 18c Széll T, Sohár I. Can. J. Chem. 1969; 47: 1254
- 18d Sipos G, Sirokmán F. Nature 1964; 202: 489
- 18e Adams JH. J. Org. Chem. 1967; 32: 3992
- 18f Zhang X.-W, Zhao DH, Quan Y.-C, Sun L.-P, Yin X.-M, Guan L.-P. Med. Chem. Res. 2010; 19: 403
- 18g Lyle RE, Paradis LP. J. Am. Chem. Soc. 1955; 77: 6667
- 19 Climent MJ, Corma A, Iborra S, Primo J. J. Catal. 1995; 151: 60
- 20 Hydrations of alkynes to ketones catalyzed by acids are known reactions. For a review, see: Hintermann L, Labonne A. Synthesis 2007; 1121 ; and references therein
For reviews, see:
For reviews, see:
For transition-metal catalyst systems for the synthesis of chalcones, see:
For selected examples with Lewis acids, see:
Selected examples with solid acids, see:
For selected examples with ionic liquids, see:
For hydration–condensation reactions of aryl alkynes with aryl aldehydes for the synthesis of chalcones, see:
For a book, see:
For low-yielding reactions, see:
For moderate-yielding reactions, see: