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Synthesis 2014; 46(07): 893-898
DOI: 10.1055/s-0033-1338591
DOI: 10.1055/s-0033-1338591
paper
One-Pot Conversion of 1-Bromo-β-carboline and 1-Bromocarbazole into Pentacyclic Compounds by Suzuki Cross-Coupling Followed by Spontaneous Cyclization
Further Information
Publication History
Received: 07 December 2013
Accepted after revision: 08 January 2014
Publication Date:
10 February 2014 (online)
Abstract
This work describes a straightforward one-pot conversion of 1-bromo-β-carboline and 1-bromocarbazole into pentacyclic compounds. Suzuki cross-coupling with various 2-methoxycarbonylphenylboronic acids was followed by spontaneous lactamization to give the target products. Coupling of 1-bromo-β-carboline with 2-formylphenylboronic acid also gave the oxo product through oxidative cyclization, whereas in the carbazole series, the intermediate hemiaminals undergo a disproportionation reaction to give both the oxo and the methylene product.
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References
-
1 Showalter HD. H. J. Nat. Prod. 2013; 76: 455
- 2 Puzik A, Bracher F. J. Heterocycl. Chem. 2009; 46: 770
- 3 Wetzel I, Allmendinger L, Bracher F. J. Nat. Prod. 2009; 72: 1908
- 4a Bracher F. Liebigs Ann. Chem. 1989; 87
- 4b Bracher F. Heterocycles 1989; 29: 2093
- 4c Bracher F. Pharmazie 1997; 52: 57
- 4d Huber K, Bracher F. Z. Naturforsch., B 2007; 62: 1313
- 4e Mink K, Bracher F. Arch. Pharm. Chem. Life Sci. 2007; 340: 429
- 4f Raeder S, Bracher F. Arch. Pharm. Pharm. Med. Chem. 2012; 345: 822
- 4g Puzik A, Bracher F. Lett. Org. Chem. 2013; 10: 568
- 4h Plodek A, Raeder S, Bracher F. Tetrahedron 2013; 69: 9857
- 5 Knölker H.-J, Reddy KR. Chem. Rev. 2002; 102: 4303
- 6 Fournet AR. F. M, Lagoutte D, Poupon E, Soriano-Agaton F. US 2011/0059977 A1, 2011
- 7 Soriano-Agaton F, Lagoutte D, Poupon E, Roblot F, Fournet A, Gantier J.-C, Hocquemiller R. J. Nat. Prod. 2005; 68: 1581
- 8a Marion L, Manske RH. F. Can. J. Res., Sect. B: Chem. Sci. 1938; 16: 432
- 8b Berti G, Bonsignori A, Da Settimo A. Ann. Chim. (Rome) 1962; 52: 1087
- 8c Shipchandler MT, Mitscher LA. J. Heterocycl. Chem. 1971; 8: 695
- 9 Plant SG. P, Tomlinson ML. J. Chem. Soc. 1932; 2188
- 10 Ghosh S, Datta DB, Datta I, Das TK. Tetrahedron 1989; 45: 3775
-
11 Markgraf JH, Dowst AA, Hensley LA, Jakobsche JE, Kaltner CJ, Webb PJ, Zimmerman PW. Tetrahedron 2005; 61: 9102
- 12 Gomez-Lor B, Echavarren AM. Org. Lett. 2004; 6: 2993
- 13 Yamuna E, Zeller M, Prasad KJ. R. Tetrahedron Lett. 2011; 52: 6030
- 14a Puzik A, Bracher F. J. Heterocycl. Chem. 2010; 47: 449
- 14b For related quinolino-canthin-4-ones, see: Dang HV, Stadlbauer W. J. Heterocycl. Chem. 2006; 43: 65
- 15 Dang HV, Knobloch B, Habib NS, Kappe T, Stadlbauer W. J. Heterocycl. Chem. 2005; 42: 85
- 16 Singh V, Hutait S, Biswas S, Batra S. Eur. J. Org. Chem. 2010; 531
- 17 Markgraf JH, Finkelstein M, Cort JR. Tetrahedron 1996; 52: 461
- 18 For successful Suzuki cross-couplings with 1-chloro-β-carboline, see: Bracher F, Hildebrand D. Liebigs Ann. Chem. 1993; 1315
- 19 Mentzel UV, Tanner D, Tønder JE. J. Org. Chem. 2006; 71: 5807
- 20 Hartung CG, Fecher A, Chapell B, Snieckus V. Org. Lett. 2003; 5: 1899
- 21a Barclay BM, Campbell N. J. Chem. Soc. 1945; 530
- 21b Gehring A, Bracher F. Synthesis 2012; 44: 2441
- 22 Bracher F, Hildebrand D. Tetrahedron 1994; 50: 12329
- 23 Yeung K.-S, Kadow JF, Grant-Young KA. WO 2008/097796 A1, 2008
- 24 Singha R, Roy S, Ray P, Ray JK. Tetrahedron Lett. 2013; 54: 657
- 25 Stahl SS. Angew. Chem. Int. Ed. 2004; 43: 3400
- 26 An impure sample of 11 has been described, see: Brown RF. C, Choi N, Coulston KJ, Eastwood FW, Ercole F, Horvath JM, Mattinson M, Mulder RJ, Ooi HC. Liebigs Ann./Recl. 1997; 1931