A Copper-Catalyzed Synthesis of Functionalized Quinazolines from Isocyanides and Aniline Tri- and Dichloroacetonitrile Adducts through Intramolecular C–H Activation

Manijeh Nematpour; Elham Rezaee; Sayyed Abbas Tabatabai; Mehdi Jahani

doi:10.1055/s-0036-15588166

Synlett, Table of Contents

Synlett 2017; 28(12): 1441-1444
DOI: 10.1055/s-0036-15588166

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A Copper-Catalyzed Synthesis of Functionalized Quinazolines from Isocyanides and Aniline Tri- and Dichloroacetonitrile Adducts through Intramolecular C–H Activation

Authors

Manijeh Nematpour

^aDepartment of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran Email: sa_tabatabai@sbmu.ac.ir
Elham Rezaee

^aDepartment of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran Email: sa_tabatabai@sbmu.ac.ir
Sayyed Abbas Tabatabai*

^aDepartment of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran Email: sa_tabatabai@sbmu.ac.ir
Mehdi Jahani

^bDepartment of Chemistry, Sharif University of Technology, Tehran, Iran

Abstract

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Abstract

A novel class of substituted quinazolines were prepared in good yields by a one-pot three-component reaction of isocyanides with adducts of anilines and tri- or dichloroacetonitrile, followed by intramolecular C–H activation, catalyzed by copper(I) iodide with l-proline as a ligand in acetonitrile at room temperature.

Keywords

C–H activation - dichloroacetonitrile - trichloroacetonitrile - copper catalysis - quinazolines - isocyanides

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References

References and Notes

1a Malecki N. Carato P. Rigo G. Goossens J.-F. Houssin R. Bailly C. Hénichart J.-P. Bioorg. Med. Chem. 2004; 12: 641
1b Gundla R. Kazemi R. Sanam R. Muttineni R. Sarma JA. R. P. Dayam R. Neamati N. J. Med. Chem. 2008; 51: 3367

2 Fry DW. Kraker AJ. McMichael A. Ambroso LA. Nelson JM. Leopold WR. Connors RW. Bridges AJ. Science 1994; 265: 1093

3a Herget T. Freitag M. Morbitzer M. Kupfer R. Stamminger T. Marschall M. Antimicrob. Agents Chemother. 2004; 48: 4154
3b Chien T.-C. Chen C.-S. Yu F.-H. Chern J.-W. Chem. Pharm. Bull. 2004; 52: 1422

4 Henderson EA. Bavetsias V. Theti DS. Wilson SC. Clauss R. Jackman AL. Bioorg. Med. Chem. 2006; 14: 5020

5a Kunes J. Bazant J. Pour M. Waisser K. Slosárek M. Janota J. Farmaco 2000; 55: 725
5b Waisser K. Gregor J. Dostál H. Kunes J. Kubicová L. Klimesová V. Kaustová J. Farmaco 2001; 56: 803

6a Lewerenz A. Hentschel S. Vissiennon Z. Michael S. Nieber K. Drug Dev. Res. 2003; 58: 420
6b Colotta V. Catarzi D. Varano F. Lenzi O. Filacchioni G. Costagli C. Galli A. Ghelardini C. Galeotti N. Gratteri P. Sgrignani J. Deflorian F. Moro S. J. Med. Chem. 2006; 49: 6015

7 Mendes da Silva JF. Walters M. Al-Damluji S. Ganellin CR. Bioorg. Med. Chem. 2008; 16: 7254

8a Lüth A. Löwe W. Eur. J. Med. Chem. 2008; 43: 1478
8b Rewcastle GW. Palmer BD. Bridges AJ. Showalter HD. H. Sun L. Nelson J. McMichael A. Kraker AJ. Fry DW. Denny WA. J. Med. Chem. 1996; 39: 918

9a Undheim K. Benneche T. In: Comprehensive Heterocyclic Chemistry II . Vol. 6. Katritzky AR. Rees CW. Scriven EV. F. Chap. 6.02 Pergamon; Oxford: 1998: 93
9b Connolly DJ. Cusack D. O’Sullivan TP. Guiry PJ. Tetrahedron 2005; 61: 10153
9c Michael JP. Nat. Prod. Rep. 2003; 20: 476
9d Shreder KR. Wong MS. Nomanbhoy T. Leventhal PS. Fuller SR. Org. Lett. 2004; 6: 3715
9e Costa M. Ca ND. Gabriele B. Massera C. Salerno G. Soliani M. J. Org. Chem. 2004; 69: 2469
9f Wiedemann SH. Ellman JA. Bergman RG. J. Org. Chem. 2006; 71: 1969
9g Fekner T. Müller-Bunz H. Guiry PJ. Org. Lett. 2006; 8: 5109
9h Kappe CO. Angew. Chem. Int. Ed. 2004; 43: 6250
9i Ferrini S. Ponticelli F. Taddei M. Org. Lett. 2007; 9: 69
9j Mizuno T. Okamoto N. Ito T. Miyata Y. Tetrahedron Lett. 2000; 41: 1051

10a Sun C.-L. Li B.-J. Shi Z.-J. Chem. Rev. 2011; 111: 1293
10b Engle KM. Mei T.-S. Wasa M. Yu J.-Q. Acc. Chem. Res. 2012; 45: 788
10c Ackermann L. Acc. Chem. Res. 2014; 47: 281
10d Neufeldt SR. Sanford MS. Acc. Chem. Res. 2012; 45: 936
10e Colby DA. Tsai AS. Bergman RG. Ellman JA. Acc. Chem. Res. 2012; 45: 814

11a Zhu C. Yi M. Wei D. Chen X. Wu Y. Cui X. Org. Lett. 2014; 16: 1840
11b Lu J. Jin Y. Liu H. Jiang Y. Fu H. Org. Lett. 2011; 13: 3694
11c Huang H. Ji X. Tang X. Zhang M. Li X. Jiang H. Org. Lett. 2013; 15: 6254
11d Oda Y. Hirano K. Satoh T. Miura M. Org. Lett. 2012; 14: 664
11e Selvaraju M. Sun C.-M. Adv. Synth. Catal. 2014; 356: 1329
11f Sang P. Xie Y. Zou J. Zhang Y. Org. Lett. 2012; 14: 3894
11g Wang Q. Schreiber SL. Org. Lett. 2009; 11: 5178
11h Xu H. Fu H. Chem. Eur. J. 2012; 18: 1180
11i Mitsuda S. Fujiwara T. Kimigafukuro K. Monguchi D. Mori A. Tetrahedron 2012; 68: 3585
11j Monguchi D. Fujiwara T. Furukawa H. Mori A. Org. Lett. 2009; 11: 1607

12a Yavari I. Nematpour M. Damghani T. Tetrahedron Lett. 2014; 55: 1323
12b Yavari I. Nematpour M. Helv. Chim. Acta 2014; 97: 1132
12c Yavari I. Nematpour M. Mol. Divers. 2015; 19: 703

13 Yavari I. Nematpour M. Sodagar E. Synlett 2013; 24: 161
14 N-Phenyl-2-(trichloromethyl)quinazolin-4-amine (5a); Typical Procedure A mixture of PhNH₂ (2a; 1 mmol) and Cl₃CCN (1a; 1 mmol) was stirred for 5 min, and then a mixture of PhNC (4a; 1.5 mmol), CuI (0.10 mmol), Cs₂CO₃ (2.0 mmol), and l-proline (20 mol%) in MeCN (2 mL) was slowly added. The mixture was stirred at r.t. for 5 h until the reaction was complete [TLC, EtOAc–hexane (1:4)]. The mixture was then diluted with CH₂Cl₂ (2 mL) and aq NH₄Cl (3 mL). The resulting mixture was stirred for 30 min, and then the phases were separated. The aqueous phase was extracted with CH₂Cl₂, and the combined organic fractions were dried (Na₂SO₄), filtered, and concentrated under reduced pressure. The resulting solid was collected by filtration and washed with hexane to give a cream-colored powder; yield: 0.29 g (85%); mp 188–190 °C. IR (KBr): 3344, 1604, 1585, 1164, 759 cm⁻¹. ¹H NMR (500 MHz, CDCl₃): δ = 5.05 (s, 1 H, NH), 7.29–7.35 (m, 3 H, Ph), 7.48 (d, ³ J = 7.7, 2 H, Ar), 7.55 (t, ³ J = 8.1, 1 H, Ar), 7.62 (t, ³ J = 8.1, 1 H, Ar), 8.02 (d, ³ J = 8.1, 1 H, Ar), 8.26 (d, ³ J = 8.1, 1 H, Ar). ¹³C NMR (125.7 MHz, CDCl₃): δ = 90.6 (CCl₃), 127.2 (CH), 127.9 (2 CH), 128.1 (CH), 128.6 (2 CH), 129.4 (CH), 130.1 (CH), 131.4 (CH), 133.8 (C), 142.7 (C), 148.0 (C), 156.2 (C), 160.1 (C). MS: m/z (%) = 338 (11) [M + 1], 259 (12), 244 (18), 128 (24), 116 (100), 92 (56), 77 (60). Anal. Calcd for C₁₅H₁₀Cl₃N₃ (338.62): C, 53.20; H, 2.98; N, 12.41. Found: C, 53.18; H, 2.95; N, 12.49.
15 Yang D. An B. Wei W. Tian L. Huang B. Wang H. ACS Comb. Sci. 2015; 17: 113

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