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 2014; 46(01): 73-80
DOI: 10.1055/s-0033-1340082
DOI: 10.1055/s-0033-1340082
paper
Ammonium Chloride-Catalyzed Three-Component Reaction for the Synthesis of Fused 4H-Chromene Derivatives in Aqueous Medium
Further Information
Publication History
Received: 17 July 2013
Accepted after revision: 10 October 2013
Publication Date:
07 November 2013 (online)
This work is dedicated to Professor Gautam Barua, former Director of the Indian Institute of Technology, Guwahati for his immense contribution in setting up and developing the Science Department of IIT Guwahati.
Abstract
An efficient one-pot process was developed to synthesize 4H-chromene derivatives using a three-component reaction involving salicylaldehydes, cyclic 1,3-diketones, and thiols in an aqueous medium at room temperature. This protocol was accomplished using the inexpensive and readily available catalyst NH4Cl. The attractive features of this protocol are: use of inexpensive catalyst NH4Cl, good yields, and mild and environmentally benign reaction conditions.
Key words
4H-chromenes - salicylaldehydes - cyclic 1,3-diketones - thiols - ammonium chloride - aqueous medium - multicomponent reactions (MCRs)Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are X-ray crystallographic data (CIF files) of 4k, spectral data of all compounds and copies of 1H, 13C NMR, and MS spectra of products.
- Supporting Information
-
References
- 1 Synthesis of Heterocycles via Multicomponent Reactions I & II. Orru RV. A, Ruijter E. Springer; Heidelberg: 2010
- 2 Li C.-J, Chan T.-H. Organic Reactions in Aqueous Media . Wiley; New York: 1997
- 3a Narayan S, Muldoon J, Finn MG, Fokin VV, Kolb HC, Sharpless KB. Angew. Chem. Int. Ed. 2005; 44: 3275
- 3b Chanda A, Fokin VV. Chem. Rev. 2009; 109: 725
- 3c Lindström UM. Chem. Rev. 2002; 102: 2751
- 4a Pirrung MC, Sarma KD. J. Am. Chem. Soc. 2004; 126: 444
- 4b Pirrung MC, Sarma KD. Tetrahedron 2005; 61: 11456
- 4c Li C.-J. Chem. Rev. 2005; 105: 3095
- 4d Li C.-J, Chen L. Chem. Soc. Rev. 2006; 35: 68
- 4e Rahmati A, Kenarkoohi T, Khavasi HR. ACS Comb. Sci. 2012; 14: 657
- 4f Zhang ZH, Lü HY, Yang SH, Gao JW. J. Comb. Chem. 2010; 12: 643
- 5a Kidwai M, Saxena S, Khan MK. R, Thukral SS. Bioorg. Med. Chem. Lett. 2005; 15: 4295
- 5b Kumar D, Reddy VB, Sharad S, Dube U, Kapur S. Eur. J. Med. Chem. 2009; 44: 3805
- 6 Wang J-L, Liu D, Zhang Z-J, Shan S, Han X, Srinivasula SM, Croce CM, Alnemri ES, Huang Z. Proc. Natl. Acad. Sci. U.S.A. 2000; 97: 7124
- 7 Shestopalov AM, Litvinov YM, Rodinovskaya LA, Malyshev OR, Semenova MN, Semenov VV. ACS Comb. Sci. 2012; 14: 484
- 8 El-Nagger AM, Abdel-El-Salam AM, Latif MS. A, Ahmed FS. M. Pol. J. Chem. 1981; 55: 793; Chem. Abstr. 1982, 97, 110378q
- 9a Kemnitzer W, Jiang S, Wang Y, Kasibhatla S, Crogan-Grundy C, Bubenik M, Labrecque D, Denis R, Lamothe S, Attardo G, Gourdeau H, Tseng B, Drewea J, Cai SX. Bioorg. Med. Chem. Lett. 2008; 18: 603
- 9b Kemnitzer W, Drewe J, Jiang S, Zhang H, Crogan-Grundy C, Labreque D, Bubenick M, Attardo G, Denis R, Lamothe S, Gourdeau H, Tseng B, Kasibhatla S, Cai SX. J. Med. Chem. 2008; 51: 417
- 10 Foloppe N, Fisher LM, Howes R, Potter A, Robertson AG. S, Surgenor AE. Bioorg. Med. Chem. 2006; 14: 4792
- 11a Foye WO. Principi Di Chemico Farmaceutica . Piccin; Padova (Italy): 1991: 416
- 11b Andreani LL, Lapi E. Bull. Chim. Farm. 1960; 99: 583 ; Chem. Abstr. 1961, 55, 12668d
- 11c Bonsignore L, Loy G, Secci D, Calignano A. Eur. J. Med. Chem. 1993; 28: 517
- 12 Limsuwan S, Trip EN, Kouwen TR. H. M, Piersma S, Hiranrat A, Mahabusarakam W, Voravuthikunchai SP, van Dijl JM, Kayser O. Phytomedicine 2009; 16: 645
- 13 Bristol JA, Gold EH, Gross I, Lovey RG. J. Med. Chem. 1981; 24: 1010
- 14a Ghosh PP, Das AR. J. Org. Chem. 2013; 78: 6170
- 14b Li M, Zhang B, Gu Y. Green Chem. 2012; 14: 2421
- 14c Li M, Gu Y. Adv. Synth. Catal. 2012; 354: 2484
- 14d Ganguly NC, Roy S, Mondal P, Saha R. Tetrahedron Lett. 2012; 53: 7067
- 14e Lesch B, Brase S. Angew. Chem. Int. Ed. 2004; 43: 115
- 15a Chen W, Cai Y, Fu X, Liu X, Lin L, Feng X. Org. Lett. 2011; 13: 4910
- 15b Babu TH, Perumal PT. Synlett 2011; 341
- 15c Murthy SN, Madhav B, Reddy VP, Nageswar YV. D. Tetrahedron Lett. 2010; 51: 3649
- 15d Kumaravel K, Vasuki G. Green Chem. 2009; 11: 1945
- 15e Elinson MN, Dorofeev AS, Miloserdov FM, Ilovaisky AI, Feducovich SK, Belyakov PA, Nikishin GI. Adv. Synth. Catal. 2008; 350: 591
- 16a Nishibayashi Y, Inada Y, Hidai M, Uemura S. J. Am. Chem. Soc. 2002; 124: 7900
- 16b Liu Y, Qian J, Lou S, Zhu J, Xu Z. J. Org. Chem. 2010; 75: 1309
- 17 Shi Y.-L, Shi M. Org. Lett. 2005; 7: 3057
- 18 Otterlo WA. L. V, Ngidi EL, Kuzvidza S, Morgans GL, Moleele SS, Koning CB. Tetrahedron 2005; 61: 9996
- 19a Fang YW, Li CZ. J. Org. Chem. 2006; 71: 6427
- 19b Malakar CC, Schmidt D, Conrad J, Beifuss U. Org. Lett. 2011; 13: 1972
- 20 Ye L.-W, Sun X.-L, Zhu C.-Y, Tang Y. Org. Lett. 2006; 8: 3853
- 21 Ramachary DB, Reddy YV, Kishor M. Org. Biomol. Chem. 2008; 6: 4188
- 22a Fan J, Wang Z. Chem. Commun. 2008; 5381
- 22b Funabiki K, Komeda T, Kubota Y, Matsui M. Tetrahedron 2009; 65: 7457
- 23a Janvier P, Sun X, Bienaymé H, Zhu J. J. Am. Chem. Soc. 2002; 124: 2560
- 23b Azizan J, Teimouri F, Mohammadizadeh MR. Catal. Commun. 2007; 8: 1117
- 24 Larsen SD, Grieco PA. J. Am. Chem. Soc. 1985; 107: 1768
- 25a Bonne D, Dekhane M, Zhu J. Org. Lett. 2004; 6: 4771
- 25b Shaabani A, Bazgir A, Teimouri F. Tetrahedron Lett. 2003; 44: 857
- 25c Dabiri M, Bahramnejad M, Baghbanzadeh M. Tetrahedron 2009; 65: 9443
- 25d Bonne D, Dekhane M, Zhu J. Org. Lett. 2005; 7: 5285
- 25e Fayol A, Zhu J. Org Lett. 2004; 6: 115
- 25f Foroughifar N, Mobinikhaledi A, Moghanian H, Mozafari R, Esfahani HR. M. Synth. Commun. 2011; 41: 2663
- 26 Khan AT, Lal M, Basha RS. Synthesis 2013; 45: 406
- 27 Nagarapu L, Karnakanti S, Bantu R, Sridhar B. Synth. Commun. 2012; 42: 967
- 28 Complete crystallographic data of 4k for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 926004. Copies of this information may be obtained free of charge from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk or via: www.ccdc.cam.ac.uk].