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-00000083.xml
Synlett 2014; 25(15): 2115-2120
DOI: 10.1055/s-0034-1378446
DOI: 10.1055/s-0034-1378446
letter
Metal-Free One-Pot Protocol for the Preparation of Unexpected Carbazole Derivative in Water: Easy Access to Pyrimidocarbazole and Pyridocarbazolone Derivatives
Further Information
Publication History
Received: 12 May 2014
Accepted after revision: 12 June 2014
Publication Date:
29 July 2014 (online)
Abstract
A novel, one-pot, metal-free-based catalytic system for the synthesis of a series of functionalized 1-methoxycarbonyl-2-aryl/alkyl-9H-carbazole derivatives has been successfully achieved in water medium by the combination of methyl 2-(3-formyl-1H-indol-2-yl)acetate with aryl/alkyl-substituted β-acroleins using DABCO (20 mol%), followed by treatment of HCl under air at heating conditions. This sequential one-pot protocol provides moderate to good yields (51–68%) of aforesaid compounds. In addition, biologically important carbazole-fused new heterocyclic scaffolds can be synthesized through our procedure.
Key words
one-pot sequential - organocatalyst - carbazole - water - pyrimidocarbazole - pyridocarbazoloneSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083. Included are experimental details and copies of 1H and 13C NMR spectra of all compounds listed in Table 3 and Schemes 2 and 3.
- Supporting Information
-
References
- 1a Zhou J. Chem. Asian J. 2010; 5: 422
- 1b Ambrosini LM, Lambert TH. ChemCatChem 2010; 2: 1373
- 1c Wende RC, Schreiner PR. Green Chem. 2012; 14: 1821
- 1d Patil NT, Shinde VS, Gajula B. Org. Biomol. Chem. 2012; 10: 211
- 1e Dai Q, Rana NK, Zhao JC.-G. Org. Lett. 2013; 15: 2922
- 1f Li F, Sun L, Teng Y, Yu P, Zhao JC.-G, Ma J.-A. Chem. Eur. J. 2012; 18: 14255
- 1g Dai Q, Arman H, Zhao JC.-G. Chem. Eur. J. 2013; 19: 1666
- 1h Fuwa H, Noguchi T, Noto K, Sasaki M. Org. Biomol. Chem. 2012; 10: 8108
- 1i Cai Q, Liang X.-W, Wang S.-G, You S.-L. Org. Biomol. Chem. 2013; 11: 1602
- 1j Cai Q, Zhao Z.-A, You S.-L. Angew. Chem. Int. Ed. 2009; 48: 7428
- 2a Tietze LF. Chem. Rev. 1996; 96: 115
- 2b Schreiber SL. Science 2000; 287: 1964
- 2c Zhu J.-P, Bienayme H. Multicomponent Reactions. Wiley-VCH; Weinheim: 2005
- 2d Trost BM. Angew. Chem., Int. Ed. Engl. 1995; 34: 259
- 2e Torssell S, Keinle M, Somfai P. Angew. Chem. Int. Ed. 2005; 44: 3096
- 3a Ahluwalia VK, Varma RS. Green Solvents for Organic Synthesis. Alpha Science International; Abingdon: 2009
- 3b Lindström UM. Organic Reactions in Water: Principles, Strategies and Applications. Blackwell; Oxford: 2007
- 3c Butler RN, Coyne AG. Chem. Rev. 2010; 110: 6302
- 3d Li C, Chan T. Organic Reactions in Aqueous Media. Wiley; New York: 1997
- 4a Schmidt AW, Reddy KR, Knölker H.-J. Chem. Rev. 2012; 112: 3193
- 4b Knölker H.-J, Reddy KR. Chemistry and Biology of Carbazole Alkaloids. In The Alkaloids. Vol. 65. Cordell GA. Academic Press; Amsterdam: 2008: 1
- 4c Roy J, Jana AK, Mal D. Tetrahedron 2012; 68: 6099
- 4d Bauer I, Knölker H.-J. Top. Curr. Chem. 2012; 309: 203
- 5a Organic Light Emitting Devices: Synthesis Properties, and Applications. Müllen K, Scherf U. Wiley-VCH; Weinheim: 2006
- 5b Tao Y, Yang C, Qin J. Chem. Soc. Rev. 2011; 40: 2943
- 5c Li J, Grimsdale A. Chem. Soc. Rev. 2010; 39: 2399
- 5d Lai SL, Tong QX, Chan MY, Ng TW, Lo MF, Ko CC, Lee ST, Lee CS. Org. Electron. 2011; 12: 541
- 6a Joule JA, Mills K. Heterocyclic Chemistry. Blackwell Science; Oxford: 2000. 4th ed.
- 6b Lin W, Wang Y, Lin S, Li C, Zhou C, Wang S, Huang H, Liu P, Ye G, Shen X. Eur. J. Med. Chem. 2012; 47: 214
- 6c Maneerat W, Ritthiwigrom T, Cheenpracha S, Promgool T, Yossathera K, Deachathai S, Phakhodee W, Laphookhieo S. J. Nat. Prod. 2012; 75: 741
- 6d Qiu Y, Ma D, Fu C, Ma S. Org. Biomol. Chem. 2013; 11: 1666
- 6e Ito C, Itoigawa M, Sato A, Hasan CM, Rashid MA, Tokuda H, Mukainaka T, Nishino H, Furukawa H. J. Nat. Prod. 2004; 67: 1488
- 6f Thongthoom T, Songsiang U, Phaosiri C, Yenjai C. Arch. Pharmacol. Res. 2010; 33: 675
- 6g Kong W, Fu C, Ma S. Chem. Eur. J. 2011; 17: 13134
- 6h Kogkathip B, Kongkathip N, Sunthitikawinsakul A, Napaswat C, Yoosook C. Phytother. Res. 2005; 19: 728
- 6i Choi TA, Czerwonka R, Fröhner W, Krahl MP, Reddy KR, Franzblau SG, Knölker H.-J. ChemMedChem 2006; 1: 812
- 6j Choi TA, Czerwonka R, Forke R, Jäger A, Knöll J, Krahl MP, Krause T, Reddy KR, Franzblau SG, Knölker H.-J. Med. Chem. Res. 2008; 17: 374
- 7a Knölker H.-J, O’Sullivan N. Tetrahedron 1994; 50: 10893
- 7b Forke R, Jäger A, Knölker H.-J. Org. Biomol. Chem. 2008; 6: 2481
- 7c Gruner KK, Knölker H.-J. Org. Biomol. Chem. 2008; 6: 3902
- 7d Börger C, Kataeva O, Knölker H.-J. Org. Biomol. Chem. 2012; 10: 7269
- 7e Ackermann L, Althammer A. Angew. Chem. Int. Ed. 2007; 46: 1627
- 7f Lu C, Markina NA, Larock RC. J. Org. Chem. 2012; 77: 11153
- 7g Tsang WC, Zheng N, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 14560
- 7h Liegault B, Lee D, Huestis MP, Stuart DR, Fagnou K. J. Org. Chem. 2008; 73: 5022
- 7i Watanabe T, Ueda S, Inuki S, Oishi S, Fujii N, Ohno H. Chem. Commun. 2007; 43: 4516
- 7j Sridharan V, Carlos MJ, Antonia MM. Eur. J. Org. Chem. 2009; 27: 4614
- 7k Jordan-Hore JA, Johansson CC. C, Gulias M, Beck EM, Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 16184
- 7l Zhu C, Ma S. Org. Lett. 2014; 16: 1542
- 7m Ozaki K, Zhang H, Ito H, Lei A, Itami K. Chem. Sci. 2013; 4: 3416
- 7n Noji T, Fujiwara H, Okano K, Tokuyama H. Org. Lett. 2013; 15: 1946
- 7o Hirano K, Inaba Y, Takasu K, Oishi S, Takemoto Y, Fujii N, Ohno H. J. Org. Chem. 2011; 76: 9068
- 7p Tsuchimoto T, Matsubayashi H, Kaneko M, Nagase Y, Miyamura T, Shirakaw E. J. Am. Chem. Soc. 2008; 130: 15825
- 7q Xie R, Ling Y, Fu H. Chem. Commun. 2012; 48: 12210
- 7r Kong W, Fu C, Ma S. Chem. Commun. 2009; 45: 4572
- 7s Grover HK, Lebold TP, Kerr MA. Org. Lett. 2011; 13: 220
- 7t Wang L, Li G, Liu Y. Org. Lett. 2011; 13: 3786
- 7u Stokes BJ, Jovanović B, Dong H, Richert K, Riell R, Driver T. J. Org. Chem. 2009; 74: 3225
- 7v Knölker H.-J, Wolper M. Tetrahedron 2003; 59: 5317
- 7w Fröhner W, Krahl MP, Reddy KR, Knölker H.-J. Heterocycles 2004; 63: 2393
- 7x Czerwonka R, Reddy KR, Baum E, Knölker H.-J. Chem. Commun. 2006; 711
- 7y Knott KE, Auschill S, Jäger A, Knölker H.-J. Chem. Commun. 2009; 1467
- 7z Gruner KK, Hopfmann T, Matsumoto K, Jäger A, Katsuki T, Knölker H.-J. Org. Biomol. Chem. 2011; 9: 2057
- 8a Xiao F, Liao Y, Wu M, Deng G.-J. Green Chem. 2012; 14: 3277
- 8b Antonchick AP, Samanta R, Kulikov K, Lategahn J. Angew. Chem. Int. Ed. 2011; 50: 8605
- 8c Cho SH, Yoon J, Chang S. J. Am. Chem. Soc. 2011; 133: 5996
- 8d Chen C.-C, Yang S.-C, Wu M.-J. J. Org. Chem. 2011; 76: 10269
- 9a Singh S, Srivastava A, Samanta S. Tetrahedron Lett. 2012; 53: 6087
- 9b Srivastava A, Singh S, Samanta S. Tetrahedron Lett. 2013; 54: 1444
- 9c Jaiswal PK, Biswas S, Singh S, Pathak B, Mobin SM, Samanta S. RSC Adv. 2013; 3: 10644
- 9d Biswas S, Jaiswal PK, Singh S, Mobin SM, Samanta S. Org. Biomol. Chem. 2013; 11: 7084
- 9e Jaiswal PK, Biswas S, Singh S, Samanta S. Org. Biomol. Chem. 2013; 11: 8410
- 10 Sheu J.-H, Chen C.-A, Chen B.-H. Chem. Commun. 1999; 203
- 11 Kamata J, Okada T, Kotake Y, Niijima J, Nakamura K, Uenaka T, Yamaguchi A, Tsukahara K, Nagasu T, Koyanagi N, Kitoh K, Yoshimatsu K, Yoshino H, Sugumi H. Chem. Pharm. Bull. 2004; 52: 1071
- 12a Sirasani G, Andrade RB. Org. Lett. 2011; 13: 4736
- 12b Dang HV, Habib NS, Kappe T, Zangger K, Stadlbauer W. J. Heterocycl. Chem. 2007; 44: 161
- 12c Prelog V, Szpilfogel S, Battegay J. Helv. Chim. Acta 1947; 30: 366
- 12d Kasturi TR, Mathew L, Sattigeri JA. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1990; 29: 1004
- 12e Fu Y, Zhang Y, He H, Hou L, Di Y, Li S, Luo X, Hao X. J. Nat. Prod. 2012; 75: 1987
- 13a Harfenist M, Magnien E. J. Org. Chem. 1963; 28: 538
- 13b Ziegler E, Rossmann U, Litvan F, Meier H. Monatsh. Chem. 1962; 93: 26
- 13c Ziegler E, Litvan F. US Patent 3052678, 1959
- 14a Lee H.-S, Kim H.-J, Kang J.-G. Photochem. Photobiol. Sci. 2011; 10: 1338
- 14b Wolfbeis OS, Ziegler E, Knierzinger A, Wipfler H, Trummer I. Monatsh. Chem. 1980; 111: 93
For reviews on one-pot sequential reactions, see:
For selected other examples, see:
Palladium-mediated carbazole synthesis, see:
Other than palladium-mediated carbazole synthesis, see:
One-pot transition-metal-free carbazole synthesis, see: