Abstract
A novel class of substituted quinolines was synthesized through a one-pot, four-component sequential reaction by intramolecular C–H activation of isocyanides with N-sulfonylamidines, catalyzed by copper(I) iodide and l-proline as a ligand in acetonitrile at room temperature. The readily available starting materials, no need for column chromatography, mild catalytic conditions, and moderate to high yields are important features of this simple one-pot reaction.
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Krafts K, Hempelmann E, Skórska-Stania A (2012) Parasitol Res 111:7
Sharma PC, Jain A, Jain S, Pahwa R, Yar MS (2010) J Enzyme Inhib Med Chem 25:577
Evans LE, Krishna A, Ma Y, Webb TE, Marshall DC, Tooke CL (2019) J Med Chem 62:4411
Nagata N, Marriott D, Harkness J, Ellis JT, Stark D (2012) Int J Parasitol Drugs Drug Resist 2:204
Abadi AH, Hegazy GH, El-Zaher AA (2005) Bioorg Med Chem 13:5759
Assefa H, Kamath S, Buolamwini JK (2003) J Comput Aided Mol Des 17:475
Scott DA, Balliet CL, Cook DJ, Davies AM, Gero TW, Omer CA (2009) Bioorg Med Chem Lett 19:697
Bi Y, Stoy P, Adam L, He B, Krupinski J, Normandin D (2004) Bioorg Med Chem Lett 14:1577
Parasea M (2013) Rev Med Chir Soc Med Nat Iasi 117:558
Wozel G, Blasum C (2014) Arch Dermatol Res 306:103
Roush GC, Sica DA (2016) Am J Hypertens 29:1130
Grant WM, Trotter RR (1954) AMA Arch Ophthalmol 51:735
Hughes JP, Rees SS, Kalindjian SB, Philpott KL (2011) Br J Pharmacol 162:1239
Ramsay RR, Popovic-Nikolic MR, Nikolic K, Uliassi E, Bolognesi ML (2018) Clin Transl Med 7:3
Bolognesi ML, Cavalli A (2016) ChemMedChem 11:1190
Meldal M, Tomøe CW (2008) Chem Rev 108:2952
Sadjadi S, Heravi MM, Nazari N (2016) RSC Adv 6:53203
Nematpour M, Rezaee E, Jahani M, Tabatabai SA (2019) J Iran Chem Soc 16:603
Yavari I, Ghazanfarpour-Darjani M, Nematpour M (2015) Tetrahedron Lett 56:2416
Nematpour M, Rezaee E, Jahani M, Tabatabai SA (2018) Tetrahedron Lett 59:2054
Nematpour M, Rezaee E, Tabatabai SA, Jahani M (2017) Synlett 28:1441
Xie X, Gai G, Ma D (2005) Org Lett 7:4693
Nazari M, Nematpour M, Rezaee E, Jahani M, Tabatabai SA (2019) J Sulfur Chem 39:646
Yang D, An B, Wei W, Tian L, Huang B, Wang H (2019) ACS Comb Sci 17:113
Acknowledgements
This work was supported by the research council of the school of pharmacy, Shahid Beheshti University of medical sciences. [Grant No. 10445].
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Sedaghat, A., Nematpour, M., Bayanati, M. et al. Synthesis of functionalized quinoline derivatives via intramolecular C–H activation reactions of N-sulfonylamidines and isocyanides. Monatsh Chem 151, 1591–1596 (2020). https://doi.org/10.1007/s00706-020-02684-5
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DOI: https://doi.org/10.1007/s00706-020-02684-5