RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
PDF herunterladen
Synlett 2016; 27(07): 1116-1120
DOI: 10.1055/s-0035-1561219
DOI: 10.1055/s-0035-1561219
letter
FeCl3-Catalyzed Three-Component One-Pot Synthesis of Novel 4-[(Benzo[d]thiazol-2-ylamino)(phenyl)methyl]-3-hydroxy-9H-xanthen-9-ones
Authors
Weitere Informationen
Publikationsverlauf
Received: 04. November 2015
Accepted after revision: 06. Dezember 2015
Publikationsdatum:
11. Januar 2016 (online)
Abstract
A novel three-component one-pot synthesis method using FeCl3 in DMF as a suitable catalyst and solvent system has been developed for the synthesis of 4-[(benzo[d]thiazol-2-ylamino)(phenyl)methyl]-3-hydroxy-9H-xanthen-9-ones. The method so developed illustrates the successful utilization of 3-hydroxyxanthones in a multicomponent reaction using a variety of aldehydes and 2-aminobenzothiazoles for the first time.
Key words
3-hydroxyxanthone - 2-aminobenzothiazole - multicomponent reaction (MCR) - 2-aminobenzothiazolomethylxanthone - ortho-quinonemethide (OQM)Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561219.
- Supporting Information (PDF)
-
References and Notes
- 1a Armstrong RW, Combs AP, Tempest PA, Brown SD, Keating TA. Acc. Chem. Res. 1996; 29: 123
- 1b Terret NK, Gardner M, Gordon DW, Kobylecki RJ, Steele J. Tetrahedron 1995; 51: 8135
- 2 Xu L.-W, Xia C.-G, Li L. J. Org. Chem. 2004; 69: 8482
- 3 Teh SS, Ee GC. L, Mah SH, Lim YM, Ahmad Z. Molecules 2013; 18: 1985
- 4 Thorson MK, Majtan T, Kraus JP, Barrios AM. Angew. Chem. Int. Ed. 2013; 52: 4641
- 5 Leao M, Gomes S, Pedraza-Chaverri J, Machado N, Sousa E, Pinto M, Inga A, Pereira C, Saraiva L. J. Nat. Prod. 2013; 76: 774
- 6a Al-Massarani SM, El Gamal AA, Al-Musayeib NM, Mothana RA, Basudan OA, Al-Rehaily AJ, Farag M, Assaf MH, El Tahir KH, Maes L. Molecules 2013; 18: 10599
- 6b Gokaraju GR, Gokaraju RR, Gokaraju VK. R. R, Golakoti T, Bhupathiraju K, Alluri VK. R. US 201345183, 2013
- 7 Ren Y, Matthew S, Lantvit DD, Ninh TN, Chai H, Fuchs JR, Soejarto DD, Carcache De Blanco EJ, Swanson SM, Kinghorn AD. J. Nat. Prod. 2011; 74: 1117
- 8 Ryu HW, Cho JK, Curtis-Long MJ, Yuk HJ, Kim YS, Jung S, Kim YS, Lee BW, Park KH. Phytochemistry 2011; 72: 2148
- 9 Verbanac D, Jain SC, Jain N, Chand M, Paljetak HČ, Matijašić M, Perić M, Stepanić V, Saso L. Bioorg. Med. Chem. 2012; 20: 3180
- 10a Ryu HW, Curtis-Long MJ, Jung S, Jin YM, Cho JK, Ryu YB, Lee WS, Park KH. Bioorg. Med. Chem. 2010; 18: 6258
- 10b Ha LD, Hansen PE, Vang O, Duus F, Pham HD, Nguyen LH. D. Chem. Pharm. Bull. 2009; 57: 830
- 11 Tanaka N, Kashiwada Y, Kim SY, Sekiya M, Ikeshiro Y, Takaishi Y. Phytochemistry 2009; 70: 1456
- 12 Lin C.-N, Won S.-J, Lieu H.-S, Liou S.-S. US 005741813A, 1998
- 13a Fernandes C, Masawang K, Tiritan ME, Sousa E, De Lima V, Afonso C, Bousbaa H, Sudprasert W, Pedro M, Pinto MM. Bioorg. Med. Chem. 2014; 22: 1049
- 13b Chen LC, Juang SH, Chang KM, Tzeng CC, Chen JJ, Chen IL, Wang TC. Chem. Pharm. Bull. 2014; 62: 106
- 14 Kasibhatla S, Cai SX, Tseng B, Jessen KA, English NM, Maliartchouk S, Jiang S, Sirisoma NS, Zhang H.-Z, Kuemmerle J. US 20050004026 A1, 2005
- 15 Zhou ZT, Wang JW. Chin. J. New Drugs 2007; 16: 79
- 16 Sun H, Chen F, Wang X, Liu Z, Yang Q, Zhang X, Zhu J, Qiang L, Guo Q, You Q. Eur. J. Med. Chem. 2012; 51: 110
- 17a Zhou T, Shi Q, Chen CH, Huang L, Ho P, Morris-Natschke SL, Lee K.-H. Eur. J. Med. Chem. 2012; 47: 86
- 17b Zhou T, Ohkoshi E, Shi Q, Bastow KF, Lee KH. Bioorg. Med. Chem. Lett. 2012; 22: 3219
- 18 Rampa A, Piazzi L, Belluti F, Gobbi S, Bisi A, Bartolini M, Andrisano V, Cavrini V, Cavalli A, Recanatini M, Valenti P. J. Med. Chem. 2001; 44: 3810
- 19 Zhang X, Li X, Sun H, Jiang Z, Tao L, Gao Y, Guo Q, You Q. Org. Biomol. Chem. 2012; 10: 3288
- 20a Delmas F, Di Giorgio C, Robin M, Azas N, Gasquet M, Detang C, Costa M, Timon-David P, Galy J.-P. Antimicrob. Agents Chemother. 2002; 46: 2588
- 20b Goguen J, Ning P, Kyungae L. WO 2009145829, 2009
- 20c Saeed S, Rashid N, Jones PG, Ali M, Hussain R. Eur. J. Med. Chem. 2010; 45: 1323
- 20d Shaban AA, Butler IS, Gilson DF. R, Bertrand JJ. C, Mouhri ZS, Mostafa MM, Mostafa SI. Inorg. Chim. Acta B 2014; 423: 242
- 20e Valderrama JA, Ríos D, Muccioli GG, Calderon PB, Brito I, Benites J. Tetrahedron Lett. 2015; 56: 5103
- 21 Dvorak HF, Zeng H (Beth Israel Deaconess Medical Center) WO 200867061, 2008
- 22a DiMauro TM, Attawia M, Toselli R, Lilienfeld S. US 200731341, 2007
- 22b Wang Y. US 200657065, 2006
- 23 Van der Valk JB. F, Vijverberg HP. M. Eur. J. Pharmacol. 1993; 232: 131
- 24a Geerts H, Nuydens R, De Jong M, Cornelissen F, Nuyens R, Wouters L. Neurobiol. Aging 1996; 17: 573
- 24b Uberti D, Rizzini C, Galli P, Pizzi M, Grilli M, Lesage A, Spano P, Memo M. Synapse 1997; 26: 95
- 25 Navarrete-Vazquez G, Ramírez-Martínez M, Estrada-Soto S, Nava-Zuazo C, Paoli P, Camici G, Escalante-García J, Medina-Franco JL, López-Vallejo F, Ortiz-Andrade R. Eur. J. Med. Chem. 2012; 53: 346
- 26a Kalavagunta PK, Bagul PK, Jallapally A, Kantevari S, Banerjee SK, Ravirala N. Eur. J. Med. Chem. 2014; 83: 344
- 26b Kalavagunta PK, Pala R, Pathipati UR, Ravirala N. J. Agric. Food Chem. 2014; 62: 6571
- 26c Venugopala KN, Krishnappa M, Nayak SK, Subrahmanya BK, Vaderapura JP, Chalannavar RK, Gleiser RM, Odhav B. Eur. J. Med. Chem. 2013; 65: 295
- 27a Agasimundin YS, Rajagopal S. J. Indian Chem. Soc. 1964; 41: 471
- 27b Passarotti M, Valenti M, Grianti M. Boll. Chim. Farm. 1994; 133: 592
- 28a Mondal A, Mukhopadhyay C. ACS Comb. Sci. 2015; 17: 404
- 28b Arias-Ugarte R, Wekesa FS, Findlater M. Tetrahedron Lett. 2015; 56: 2406
- 28c He X, Shang Y, Yu Z, Fang M, Zhou Y, Han G, Wu F. J. Org. Chem. 2014; 79: 8882
- 29 General Procedure: 3-Hydroxyxanthone (1 mmol), benzaldehyde (1 mmol), and 2-aminobenzothiazole (1 mmol) were added to a 10 mL round-bottom flask. To this DMF (0.3 mL) was added, followed by 0.2 equiv of FeCl3. The resulting mixture was heated at 120 °C until the reaction was completed as indicated by TLC (ca. 2 h). The reaction mixture is then cooled to r.t., quenched with H2O, extracted with EtOAc, the combined extracts dried, filtered, the solvent removed, and the residue purified by column chromatography. 4-[(Benzo[d]thiazol-2-ylamino)(phenyl)methyl]-3-hydroxy-9H-xanthen-9-one (4e) Compound 4e was obtained in 91% yield as an off-white solid; mp 180 °C. 1H NMR (400 MHz, DMSO-d 6): δ = 11.73–11.12 (br s, 1 H), 8.85 (d, 1 H, J = 7.8 Hz), 8.11 (dd, 1 H, J 1 = 7.8 Hz, J 2 = 1.2 Hz), 8.03 (d, 1 H, J = 8.8 Hz), 7.81 (dt, 1 H, J 1 = 8.8 Hz, J 2 = 1.2 Hz), 7.67 (d, 1 H, J = 7.8 Hz), 7.60 (d, 1 H, J = 8.8 Hz), 7.47 (d, 2 H, J = 7.8 Hz), 7.42 (t, 1 H, J = 7.8 Hz), 7.37–7.29 (m, 3 H), 7.22–7.13 (m, 3 H), 7.06 (d, 1 H, J = 8.8 Hz), 7.01 (t, 1 H, J = 6.8 Hz). 13C NMR (100 MHz, DMSO-d 6): δ = 175.4, 166.2, 161.5, 155.8, 152.6, 142.2, 135.1, 131.1, 128.6, 127.3, 127.0, 126.6, 126.0, 125.9, 124.6, 121.5, 121.4, 121.3, 118.8, 118.6, 115.7, 114.8, 114.1, 52.1. IR: νmax = 3270, 3062, 1639, 1617, 1604, 1573, 1538, 1466, 1439, 1310, 1221, 1148, 1058, 1033, 754, 698 cm–1. LC–MS: m/z = 449 [M – H]. HRMS: m/z calcd for C27H19O3N2S: 451.1111; found: 451.1085.