A Novel Copper-Catalyzed Synthesis of N-Monosubstituted 2-Alkynimidamides from 1-Alkynes and Trichloroacetamidines

Author(s): Hossein Fasihi Dastjerdi, Manijeh Nematpour, Elham Rezaee, Mehdi Jahani, Sayyed Abbas Tabatabai*

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 9 , 2020


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Graphical Abstract:


Abstract:

A one-pot Cu-catalyzed synthesis of functionalized alkynyl imidamide by terminal alkynes, trichloroacetonitrile and aniline or benzyl amine is reported. The compounds were produced via coupling reaction of terminal alkynes with trichloroacetamidine. This method was performed under mild, ligand-free conditions and easy work-up method.

Keywords: Terminal alkynes, copper iodide, alkynylimidamide, cross-coupling, aniline, one-pot reaction.

[1]
Likhar, P.R.; Subhas, M.S.; Roy, S.; Kantam, M.L.; Sridhar, B.; Seth, R.K.; Biswas, S. Org. Biomol. Chem., 2009, 7(1), 85-93.
[http://dx.doi.org/10.1039/B815398A] [PMID: 19081950]
[2]
Kel’in, A.V.; Sromek, A.W.; Gevorgyan, V. J. Am. Chem. Soc., 2001, 123(9), 2074-2075.
[http://dx.doi.org/10.1021/ja0058684] [PMID: 11456838]
[3]
Sromek, A.W.; Rheingold, A.L.; Wink, D.J.; Gevorgyan, V. Synlett, 2006, 2325-2328.
[4]
Friebolin, W.; Eberbach, W. Helv. Chim. Acta, 2001, 84, 3822-3836.
[http://dx.doi.org/10.1002/1522-2675(20011219)84:12<3822:AID-HLCA3822>3.0.CO;2-O]
[5]
Sha, F.; Huang, X. Angew. Chem. Int. Ed., 2009, 121, 3510-3513.
[http://dx.doi.org/10.1002/ange.200900212]
[6]
Ueda, M.; Ikeda, Y.; Sato, A.; Ito, Y.; Kakiuchi, M.; Shono, H.; Miyoshi, T.; Naito, T.; Miyata, O. Tetrahedron, 2011, 67, 4612-4615.
[http://dx.doi.org/10.1016/j.tet.2011.04.083]
[7]
Mangelinckx, S.; Rooryck, S.; Jacobs, J.; De Kimpe, N. Tetrahedron Lett., 2007, 48, 6535-6538.
[http://dx.doi.org/10.1016/j.tetlet.2007.07.047]
[8]
Zhang, F.G.; Ma, H.; Zheng, Y.; Ma, J.A. Tetrahedron, 2012, 68, 7663-7669.
[http://dx.doi.org/10.1016/j.tet.2012.05.086]
[9]
Rahm, R.; Espenlaub, S.; Werz, U.R.; Maas, G. Heteroatom Chem., 2005, 16, 437-446.
[http://dx.doi.org/10.1002/hc.20131]
[10]
Feng, L.; Kerwin, S.M. Tetrahedron Lett., 2003, 44, 3463-3466.
[http://dx.doi.org/10.1016/S0040-4039(03)00675-0]
[11]
Josephsohn, N.S.; Snapper, M.L.; Hoveyda, A.H. J. Am. Chem. Soc., 2004, 126(12), 3734-3735.
[http://dx.doi.org/10.1021/ja049388e] [PMID: 15038725]
[12]
Gerster, H.; Espenlaub, S.; Maas, G. Synthesis, 2006, 2251-2259.
[13]
Schlegel, J.; Maas, G. Synthesis, 1999, 100-106.
[http://dx.doi.org/10.1055/s-1999-3697]
[14]
Miura, M.; Enna, M.; Okuro, K.; Nomura, M. J. Org. Chem., 1995, 60, 4999-5004.
[http://dx.doi.org/10.1021/jo00121a018]
[15]
Bishop, B.C.; Brands, K.M.; Gibb, A.D.; Kennedy, D.J. Synthesis, 2004, 43-52.
[16]
Yavari, I.; Nasiri‐Gheidari, S. Helv. Chim. Acta, 2011, 94, 811-816.
[http://dx.doi.org/10.1002/hlca.201000279]
[17]
Yavari, I.; Nematpour, M. Helv. Chim. Acta, 2014, 97, 384-387.
[http://dx.doi.org/10.1002/hlca.201300214]
[18]
Yavari, I.; Nematpour, M. Tetrahedron Lett., 2013, 54, 4973-4974.
[http://dx.doi.org/10.1016/j.tetlet.2013.07.029]
[19]
Yavari, I.; Nematpour, M.; Sodagar, E. Synlett, 2013, 161-164.
[http://dx.doi.org/10.1055/s-0032-1317952]
[20]
Nematpour, M.; Abedi, E.; Abedi, E. Lett. Org. Chem., 2019, 16, 99-103.
[http://dx.doi.org/10.2174/1570178615666180914114010]
[21]
Nematpour, M.; Abedi, E.; Abedi, E.; Lotfi, M. Lett. Org. Chem., 2018, 15, 727-730.
[http://dx.doi.org/10.2174/1570178614666170810125505]


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Article Details

VOLUME: 17
ISSUE: 9
Year: 2020
Published on: 16 September, 2020
Page: [704 - 708]
Pages: 5
DOI: 10.2174/1570178616666191023142821
Price: $65

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