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Synthesis 2015; 47(23): 3797-3804
DOI: 10.1055/s-0035-1560068
DOI: 10.1055/s-0035-1560068
paper
New Chiral Benzimidazoles Derived from 1,2-Diaminocyclohexane
Further Information
Publication History
Received: 02 June 2015
Accepted after revision: 09 July 2015
Publication Date:
17 August 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201523/lookinside/thumbnails/ss-2015-t0352-op_10-1055_s-0035-1560068-1.jpg)
Abstract
A simple synthesis of new enantiomeric benzimidazoles was developed. Starting from readily available enantiomeric trans-1,2-diaminocyclohexane, the respective products were obtained in 3–4 steps in moderate to fair yields. A series of ten benzimidazoles substituted at the position 2 with alkyl, aryl, and heteroaryl groups were prepared.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560068.
- Supporting Information
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References
- 1a Bansal Y, Silakari O. Bioorg. Med. Chem. 2012; 20: 6208
- 1b Shah K, Chhabra S, Shrivastava PM. Med. Chem. Res. 2013; 22: 5077
- 1c Narasimhan B, Sharma D, Kumar P. Med. Chem. Res. 2012; 21: 269
- 1d Spasov AA, Yozhitsa IN, Bugaeva LI, Anisimova VA. Pharm. Chem. J. 1999; 33: 232
- 2a Xu H, Zheng L, Liu Q, Wang L, Zhang S. J. Heterocycl. Chem. 2012; 49: 1108
- 2b Karnik AV, Kamath SS. J. Org. Chem. 2007; 72: 7435
- 2c Karnik AV, Kamath SS. Tetrahedron: Asymmetry 2008; 19: 45
- 2d Mirgane NA, Karnik AV. Chirality 2011; 23: 404
- 2e Reddy KR, Krishna GG, Rajasekhar CV. Synth. Commun. 2007; 37: 4289
- 2f Lacoste E, Vaique E, Berlande M, Pianet I, Vincent J.-M, Landais Y. Eur. J. Org. Chem. 2007; 167
- 2g Gómez-Torres E, Alonso DA, Gómez-Beongs E, Nájera C. Eur. J. Org. Chem. 2013; 1434
- 3 For review, see: Téllez F, López-Sandoval H, Castillo-Blum SE, Barba-Behrens N. ARKIVOC 2008; (v): 245
- 4a Li X.-N, Zhou H.-Y, Feng L, Duan K, Wang J.-X. Appl. Organomet. Chem. 2012; 26: 168
- 4b Li Y, Ding Sandoval CA. Org. Lett. 2009; 11: 907
- 4c Weemers JJ. M, Sypaseuthm FD, Bäerlein PS, van der Graaff WN. P, Filot IA. W, Lutz M, Müller C. Eur. J. Org. Chem. 2014; 350
- 4d Sun W.-H, Hao P, Zhang S, Shi W, Zuo W, Tang X, Lu X. Organometallics 2007; 26: 2720
- 5 For a review, see: Bennani YL, Hanessian S. Chem. Rev. 1997; 97: 3167
- 6a Shi M, Qian HX. Tetrahedron 2005; 61: 4949
- 6b Li Y, Tang J, Gu J, Wang Q, Sun P, Zhang D. Organometallics 2014; 33: 876
- 6c Shigeng B, Tang J, Zhang D, Wang Q, Chen Z, Weng L. J. Organomet. Chem. 2012; 700: 223
- 7 Shi M, Qian H. Appl. Organomet. Chem. 2005; 19: 1083
- 8a Grimmett MR. Imidazole and Benzimidazole Synthesis (Best Synthetic Methods). Academic Press; San Diego: 1997
- 8b Preston PN. Chem. Rev. 1974; 74: 279
- 9a Xue D, Long Y.-Q. J. Org. Chem. 2014; 79: 4727
- 9b Pizzetti M, De Luca E, Petricci E, Porcheddu A, Taddei M. Adv. Synth. Catal. 2012; 354: 2453
- 10 Rivas FM, Giessert AJ, Diver ST. J. Org. Chem. 2002; 67: 1708
- 11 Lee JB, Doucette A, Wilson NS, Lord J. Tetrahedron Lett. 2001; 42: 2635
- 12 In the reaction of 6a with salicylaldehyde, the corresponding imine was isolated in 10% yield. Furthermore, the corresponding reaction with 2-nitrobenzaldehyde monitored by MS revealed after one day at 25 °C the presence of imine only (HRMS: m/z calcd: 463.1895; found: 463.1891).
- 13a Muller G, Maupin CL, Riehl JP, Birkedal H, Piguet C, Bünzli J.-CG. Eur. J. Inorg. Chem. 2003; 4065
- 13b Muller G, Riehl JP, Schenk KJ, Hopfgartner G, Piguet C, Bünzli J.-CG. Eur. J. Inorg. Chem. 2002; 3101
- 14a Lücing U, Chen J, Rudkevich DM, Rebek JJr. J. Am. Chem. Soc. 2001; 123: 9929
- 14b Zhang M, Hao P, Zuo W, Jie S, Sun W.-H. J. Organomet. Chem. 2008; 693: 483
- 14c Zhang M, Zhang S, Hao P, Jie S, Sun W.-H, Li P, Lu X. Eur. J. Org. Inorg. Chem. 2007; 3816
- 14d Ryan PE, Guenee L, Piguet C. Dalton Trans. 2013; 42: 11047
- 15 Wu T, Zhang X.-P, Li C.-H, Bouř P, Li Y.-Z, You X.-Z. Chirality 2012; 24: 451
For reviews, see:
For racemic compound, see:
For enantiomeric products, see:
General reviews of benzimidazole synthesis: