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-00000084.xml
Synthesis 2014; 46(05): 600-606
DOI: 10.1055/s-0033-1340486
DOI: 10.1055/s-0033-1340486
paper
Synthesis of H-Pyrazolo[5,1-a]isoquinolines via Silver(I)-Catalyzed Tandem Reaction of N′-(2-Alkynylbenzylidene)hydrazides with Propargyl Amine Derivatives
Further Information
Publication History
Received: 15 November 2013
Accepted after revision: 05 December 2013
Publication Date:
10 January 2014 (online)
Abstract
We have developed a tandem reaction of N′-(2-alkynylbenzylidene)hydrazides with propargyl amine derivatives catalyzed by silver triflate to provide 2-(aminomethyl)-H-pyrazolo[5,1-a]isoquinolines. This reaction proceeds through a tandem 6-endo-cyclization, nucleophilic addition, 5-endo-cyclization and aromatization, leading to the cycloadducts in moderate to good yields with exclusive regioselectivity.
Key words
N′-(2-alkynylbenzylidene)hydrazides - propargyl amine derivatives - silver triflate - tandem reactions - 1,3-dipolar cycloaddition reactionsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a 1,3-Dipolar Cycloaddition Chemistry . Padwa A. Wiley; New York: 1984
- 1b Gothelf KV, Jørgensen KA. Chem. Rev. 1998; 98: 863
- 1c Cycloaddition Reactions in Organic Synthesis . Kobayashi S, Jørgensen KA. Wiley-VCH; Weinheim: 2001
- 1d Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Towards Heterocycles and Natural Products. Padwa A, Pearson WH. Wiley; New York: 2002
- 1e Adrio J, Carretero JC. Chem. Commun. 2011; 47: 6784
- 1f Stanley LM, Sibi MP. Chem. Rev. 2008; 108: 2887
- 1g Kissane M, Maguire AR. Chem. Soc. Rev. 2010; 39: 845
- 1h Patil NT, Yamamoto Y. Chem. Rev. 2008; 108: 3395
- 2a Hashimoto T, Maeda Y, Omote M, Nakatsu H, Maruoka K. J. Am. Chem. Soc. 2010; 132: 4076
- 2b Hashimoto T, Omote M, Maruoka K. Angew. Chem. Int. Ed. 2011; 50: 3489
- 2c Soeta T, Tamura K, Ukaji Y. Org. Lett. 2012; 14: 1226
- 3a Shintani R, Fu GC. J. Am. Chem. Soc. 2003; 125: 10778
- 3b Suárez A, Downey CW, Fu GC. J. Am. Chem. Soc. 2005; 127: 11244
- 3c Keller M, Sani Souna Sido A, Pale P, Sommer J. Chem. Eur. J. 2009; 15: 2810
- 3d Yoshimura K, Oishi T, Yamaguchi K, Mizuno N. Chem. Eur. J. 2011; 17: 3827
- 3e Luo N, Zheng Z, Yu Z. Org. Lett. 2011; 13: 3384
- 3f Imaizumi T, Yamashita Y, Kobayashi S. J. Am. Chem. Soc. 2012; 134: 20049
- 3g Chen W, Yuan X.-H, Li R, Du W, Wu Y, Ding L.-S, Chen Y.-C. Adv. Synth. Catal. 2006; 348: 1818
- 3h Chen W, Du W, Duan Y.-Z, Wu Y, Yang S.-Y, Chen Y.-C. Angew. Chem. Int. Ed. 2007; 46: 7667
- 3i Suga H, Funyu A, Kakehi A. Org. Lett. 2007; 9: 97
- 3j Sibi MP, Rane D, Stanley LM, Soeta T. Org. Lett. 2008; 10: 2971
- 3k Li J, Lian X, Liu X, Lin L, Feng X. Chem. Eur. J. 2013; 19: 5134
- 3l Na R, Jing C, Xu Q, Jiang H, Wu X, Shi J, Zhong JC, Wang M, Benitez D, Tkatchouk E, Goddard WA, Guo HC, Kwon O. J. Am. Chem. Soc. 2011; 133: 13337
- 3m Wang D, Deng H.-P, Wei Y, Xu Q, Shi M. Eur. J. Org. Chem. 2013; 401
- 3n Liu Y, Zhen W, Dai W, Wang F, Li X. Org. Lett. 2013; 15: 874
- 3o Qian Y, Zavalij PJ, Hu W, Doyle MP. Org. Lett. 2013; 15: 1564
- 4a Dzierszinski F, Coppin A, Mortuaire M, Dewally E, Slomianny C, Ameisen J.-C, Debels F, Tomavo S. Antimicrob. Agents Chemother. 2002; 46: 3197
- 4b Kletsas D, Li W, Han Z, Papadopoulos V. Biochem. Pharmacol. 2004; 67: 1927
- 4c Muscarella DE, O’Brien KA, Lemley AT, Bloom SE. Toxicol. Sci. 2003; 74: 66
- 4d Marco E, Laine W, Tardy C, Lansiaux A, Iwao M, Ishibashi F, Bailly C, Gago F. J. Med. Chem. 2005; 48: 3796
- 4e Kluza J, Gallego M.-A, Loyens A, Beauvillain J.-C, Fernandez Sousa-Faro J.-M, Cuevas C, Marchetti P, Bailly C. Cancer Res. 2006; 66: 3177
- 5a Lober S, Hubner H, Gmeiner P. Bioorg. Med. Chem. Lett. 2002; 12: 2377
- 5b Hasen JB, Weis J, Suzdak PD, Eskesen K. Bioorg. Med. Chem. Lett. 1994; 4: 695
- 5c Bettinetti L, Schlotter K, Hubner H, Gmeiner P. J. Med. Chem. 2002; 45: 4594
- 5d Johns BA, Gudmundsson KS, Turner EM, Allen SH, Samano VA, Ray JA, Freeman GA, Boyd FL. Jr, Sexton CJ, Selleseth DW, Creech KL, Moniri KR. Bioorg. Med. Chem. 2005; 13: 2397
- 5e Akahane A, Katayama H, Mitsunaga T, Kato T, Kinoshita T, Kita Y, Kusunoki T, Terai T, Yoshida K, Shiokawa Y. J. Med. Chem. 1999; 42: 779
- 6a Chen Z, Wu J. Org. Lett. 2010; 12: 4856
- 6b Chen Z, Yu X, Wu J. Chem. Commun. 2010; 46: 6356
- 6c Chen Z, Pan X, Wu J. Synlett 2011; 964
- 6d Li S, Wu J. Org. Lett. 2011; 13: 712
- 6e Ye S, Yang X, Wu J. Chem. Commun. 2010; 46: 5238
- 6f Yu X, Ye S, Wu J. Adv. Synth. Catal. 2010; 352: 2050
- 6g Yu X, Chen Z, Yang X, Wu J. J. Comb. Chem. 2010; 12: 374
- 6h Chen Z, Yang X, Wu J. Chem. Commun. 2009; 3469
- 6i Chen Z, Ding Q, Yu X, Wu J. Adv. Synth. Catal. 2009; 351: 1692
- 6j Chen Z, Su M, Yu X, Wu J. Org. Biomol. Chem. 2009; 7: 4641
- 7a Huang P, Chen Z, Yang Q, Peng Y. Org. Lett. 2012; 14: 2790
- 7b Huang P, Yang Q, Chen Z, Ding Q, Xu J, Peng Y. J. Org. Chem. 2012; 77: 8092
- 8a Lu T, Lu Z, Ma Z.-X, Zhang Y, Hsung RP. Chem. Rev. 2013; 113: 4862
- 8b Wei L.-L, Xiong H, Hsung RP. Acc. Chem. Res. 2003; 36: 773
- 9a Wei L.-L, Mulder JA, Xiong H, Zificsak CA, Douglas CJ, Hsung RP. Tetrahedron 2001; 57: 459
- 9b Lohse AG, Hsung RP. Org. Lett. 2009; 11: 3430
- 9c Rao W, Joo Koh M, Kothandaraman P, Chan PW. H. J. Am. Chem. Soc. 2012; 134: 10811
- 9d Li X.-X, Zhu L.-L, Zhou W, Chen Z. Org. Lett. 2012; 14: 436
- 9e González-Gómez Á, Añorbe L, Poblador A, Domínguez G, Pérez-Castells J. Eur. J. Org. Chem. 2008; 1370
- 10a Liu H, Liu G, Pu S, Wang Z. Org. Biomol. Chem. 2013; 11: 2898
- 10b Zheng D, Wang Z, Wu J. Synthesis 2011; 2810
- 11 Crystallographic data for 3a have been deposited at the Cambridge Crystallographic Data Centre, with the deposition number CCDC 953132. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk] or via www.ccdc.cam.ac.uk/data_request/cif.
For selected reviews of 1,3-dipolar cycloadditions, see:
For selected examples of the reactions of C,N-cyclic azomethine imines, see:
For selected examples of the reactions of N,N′-cyclic azomethine imines, see:
For selected examples, see:
For reviews of allenamides, see:
For selected examples, see: