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Synlett 2013; 24(16): 2124-2126
DOI: 10.1055/s-0033-1339521
DOI: 10.1055/s-0033-1339521
letter
An Approach to the Synthesis of 2-Acylchromeno[3,4-c]pyrrol-4(2H)-one Derivatives via a Sequential Three-Component Reaction
Further Information
Publication History
Received: 16 June 2013
Accepted after revision: 17 July 2013
Publication Date:
02 September 2013 (online)
Abstract
An efficient synthesis of 2-acylchromeno[3,4-c]pyrrol-4(2H)-one derivatives by a three-component reaction of salicylaldehydes, β-keto esters, and p-toluenesulfonylmethyl isocyanide is reported.
Key words
2-acylchromeno[3,4-c]pyrrol-4(2H)-one - p-toluenesulfonylmethyl isocyanide - salicylaldehyde - [1,3]-acyl shiftSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
- 1 Coumarins: Occurrence, Chemistry and Biochemistry. John Wiley and Sons; New York: 1982: 21
- 2 Murray RD. H In Progress in the Chemistry of Organic Natural Products . Vol. 83. Herz W, Falk H, Kirby GW, Moore RE. Springer; Wien: 2002: 1-529
- 3 Wang CJ, Hsieh YJ, Chu CY, Lin YL, Tseng TH. Cancer Lett. 2002; 183: 163
- 4 Cravotto G, Nano GM, Palmisano G, Tagliapietra S. Tetrahedron: Asymmetry 2001; 12: 707
- 5 Fan GJ, Mar W, Park MK, Wook Choi E, Kim K, Kim S. Bioorg. Med. Chem. Lett. 2001; 11: 2361
- 6 Kirkiacharian S, Thuy DT, Sicsic S, Bakhchinian R, Kurkjian R, Tonnaire T. Farmaco 2002; 57: 703
- 7 Kennedy RO, Zhorenes RD. Coumarins: Biology, Applications and Mode of Action. John Wiley and Sons; Chichester: 1997
- 8 Zabradnik M. The Production and Application of Fluorescent Brightening Agents. John Wiley and Sons; New York: 1992
- 9a Mustafa A, Starkovsky NA, Salama TI. J. Org. Chem. 1961; 26: 890
- 9b Unangst PC, Capiris T, Connor DT, Heffner TG, MacKenzie RG, Miller SR, Pugsley TA, Wise LD. J. Med. Chem. 1997; 40: 2688
- 9c Hanamoto T, Hashimoto E, Miura M, Furuno H, Inanaga J. J. Org. Chem. 2008; 73: 4736
- 9d Jadidi K, Ghahremanzadeh R, Bazgir A. J. Comb. Chem. 2009; 11: 341
- 9e Majumdar KC, Samanta SK. Tetrahedron Lett. 2002; 43: 2119
- 9f Symeonidis TS, Kallitsakis MG, Litinas KE. Tetrahedron Lett. 2011; 52: 5452
- 9g Moshkin VS, Sosnovskikh VY, Röschenthaler GV. Tetrahedron Lett. 2012; 53: 3568
- 10 Varman RS, Dahiya R. J. Org. Chem. 1998; 63: 8038
- 11a Wang Q, Finn MG. Org. Lett. 2000; 2: 4063
- 11b Petasis NA, Butkevich AN. J. Organomet. Chem. 2009; 694: 1747
- 12 Youn SW, Eom JI. Org. Lett. 2005; 7: 3355
- 13 Ravichandran S. Synth. Commun. 2001; 31: 1233
- 14 Majumdar N, Korthals KA, Wulff WD. J. Am. Chem. Soc. 2012; 134: 1357
- 15a Smith ND, Huang D, Cosford ND. P. Org. Lett. 2002; 4: 3537
- 15b Sisko J, Kassick AJ, Mellinger M, Filan JJ, Allen A, Olsen MA. J. Org. Chem. 2000; 65: 1516
- 15c Mendiola J, Minguez JM, Alvarez-Builla J, Vaquero JJ. Org. Lett. 2000; 2: 3253
- 15d Kelly JM, Leeper FJ. Tetrahedron Lett. 2012; 53: 819
- 15e Krishna PR, Sekhara ER. Adv. Synth. Catal. 2008; 350: 2871
- 15f Otto H, Oldenziel OH, van Leusen D, van Leusen AM. J. Org. Chem. 1977; 42: 3114
- 15g Have RT, Huisman M, Meetsma A, van Leusen AM. Tetrahedron 1997; 53: 11355
- 15h Hundscheid FJ. A, Tandon VK, Rouwette PH. F. M, van Leusen AM. Tetrahedron 1987; 43: 5073
- 15i van Nispen SP. J. M, Mensink C, van Leusen AM. Tetrahedron Lett. 1980; 21: 3723
- 15j van Leusen D, Rouwette PH. F. M, van Leusen AM. J. Org. Chem. 1981; 46: 5159
- 15k Moskal J, van Stralen P, Postma D, van Leusen AM. Tetrahedron Lett. 1986; 27: 2173
- 15l van Leusen AM, Hoogenboom BE, Houwing HA. J. Org. Chem. 1976; 41: 711
- 15m Have RT, Leusink F, R. Van Leusen AM. Synthesis 1996; 871
- 15n Dömling A. Chem. Rev. 2006; 106: 17
- 16a Alizadeh A, Ghanbaripour R. Helv. Chim. Acta 2013; 96: 473
- 16b Zohreh N, Alizadeh A. Tetrahedron 2011; 67: 4595
- 16c Alizadeh A, Mokhtari J, Ahmadi M. Tetrahedron 2012; 68: 319
- 16d Rezvanian A, Alizadeh A, Zhu LG. Synlett 2012; 23: 2526
- 16e Alizadeh A, Rezvanian A, Zhu LG. J. Org. Chem. 2012; 77: 4385
- 16f Alizadeh A, Ghanbaripour R, Zhu LG. Synth. Commun. 2013; 43: 2575
- 17a Tan J, Xu X, Zhang L, Li Y, Liu Q. Angew. Chem. Int. Ed. 2009; 48: 2868
- 17b Jiménez-Núñez E, Echavarren AM. Chem. Commun. 2007; 333
- 17c Sarpong R, Su JT, Stoltz BM. J. Am. Chem. Soc. 2003; 125: 13624
- 17d Amijs CH. M, Lopez-Carrillo V, Echavarren AM. Org. Lett. 2007; 9: 4021
- 17e Jones GO, Li X, Hayden AE, Houk KN, Danishefsky SJ. Org. Lett. 2008; 10: 4093
- 18 To a solution of salicylaldehyde 1 (1 mmol) and β-keto ester 2 (1 mmol) in DMF (2 mL), piperidine (0.1 mmol) was added, and the solution was stirred for 1 h at r.t. Then, Et3N (1 mmol) and TosMIC (1 mmol) were dissolved in DMF (2 mL) and added to the reaction mixture. Upon completion of the reaction as monitored by TLC (7 h), the mixture was filtered, and the precipitate was washed with EtOH (4 mL) to afford the pure product 3a–j.
- 19 Frolova LV, Malik I, Uglinskii PY, Rogelj S, Kornienko A, Magedov IV. Tetrahedron Lett. 2011; 52: 6643