Synlett 2017; 28(12): 1441-1444
DOI: 10.1055/s-0036-15588166
letter
© Georg Thieme Verlag Stuttgart · New York

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

Manijeh Nematpoura, Elham Rezaeea, Sayyed Abbas Tabatabai*a, Mehdi Jahanib
  • aDepartment of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran   Email: sa_tabatabai@sbmu.ac.ir
  • bDepartment of Chemistry, Sharif University of Technology, Tehran, Iran
Further Information

Publication History

Received: 08 January 2017

Accepted after revision: 08 March 2017

Publication Date:
11 April 2017 (eFirst)

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.

Supporting Information

 
  • References and Notes

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  • 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.
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