Copper(I)‐Catalyzed N‐Carboxamidation of Indoles with Isocyanates: Facile and General Method for the Synthesis of Indole‐1‐carboxamides

Abstract

A facile and general method for the synthesis of indole‐1‐carboxamides was developed via copper(I)‐catalyzed N‐carboxamidation of indoles with isocyanates under mild reaction conditions. This process is scalable and tolerates a wide spectrum of indoles and isocyanates to deliver corresponding products in good to excellent yields, providing a viable synthetic approach to indole‐1‐carboxamides, which can be used for the treatment of inflammatory diseases and diabetes.

Synthesis of Indole-Fused Oxepines via CH Activation Initiated Diastereoselective [5 + 2] Annulation of Indoles with 1,6-Enynes

“…N-substituted carboxamides indoles 1 were prepared according to the literature [1,2,3] and all data were in agreement with these reported [1,2,3] .…”

“…260 -262 ℃. 1 H NMR (400 MHz, DMSO-d6) δ 11.33 (s, 1H), 7.57 (d, J = 7.9 Hz, 1H), 7.43 -7.27 (m, 6H), 7.19 (s, 1H), 7.13 (t, J = 7.5 Hz, 1H), 6.99 (t, J = 7. 5 Hz,1H),6.74 (d,J = 10.2 Hz,1H),6.16 (d,J = 10.2 Hz,1H),4.91 (d,J = 16.0 Hz,1H),4.66 (d,J = 16.0 Hz,1H),3.95 (dd,J = 12.7,5.7 Hz,1H),2.84 (dd,J = 17.1,12.7 Hz,1H),2.45 (dd,J = 17.1,5.7 Hz,1H), 1.29 (s, 3H) ppm; 13 C NMR (100 MHz, DMSO-d6) δ 198.…”

“…235 -237 ℃. 1 H NMR (400 MHz,1H),7H),7.19 (s,1H),6.96 (td,J = 9.3,2.4 Hz,1H),6.74 (d,J = 10.2 Hz,1H),6.16 (d,J = 10.2 Hz,1H),4.91 (d,J = 16.1 Hz,1H),4.65 (d,J = 16.1 Hz,1H),3.94 (dd,J = 12.5,5.8 Hz,1H),2.82 (dd,J = 17.2,12.5 Hz,1H),2.46 (dd,J = 17.2,5.8 Hz,1H),1.30 (s,3H) ppm; 13 C NMR (100 MHz, 1 JC-F = 231. 5 Hz), 156.0 (C-F, 1 JC-F = 231.…”

“…> 270 ℃. 1 H NMR ( 400MHz, DMSO-d6) δ 11.52 (s, 1H), 7.69 (d, J = 1. 6 Hz,1H),6H),7.19 (s, 1H), 7.11 (dd, J = 8.6, 1.9 Hz, 1H), 6.72 (d, J = 10.2 Hz, 1H), 6.15 (d, J = 10.2 Hz, 1H), 4.90 (d, J = 16.…”

“…> 270 ℃. 1 H NMR (400 MHz,1H),7.83 (s,1H),6H),7.22 (dd,J = 8.6,1.3 Hz,1H),7.19 (s,1H),6.72 (d,J = 10.2 Hz,1H),6.15 (d,J = 10.2 Hz,1H),4.90 (d,J = 16.1 Hz,1H),4.63 (d,J = 16.1 Hz,1H),3.98 (dd,J = 12.7,5.7 Hz,1H),2.79 (dd,J = 17.2,12.7 Hz,1H),2.43 (dd,J = 17.2,5.7 Hz,1H), 1.27 (s, 3H) ppm; 13 C NMR (100 MHz, DMSO-d6) δ 198.3, 150.6, 135.9, 135.6, 134.7, 133.5, 130.2, 129.6, 129.3, 128.4, 127.4, 126.0, 124.5, 120.2, 113.5, 112.9, 111.7, 74.0, 62.1, 43.4, 37.5, 27.3 ppm;FTIR (neat) υ 3408, 2922FTIR (neat) υ 3408, , 1724FTIR (neat) υ 3408, , 1677FTIR (neat) υ 3408, , 1445FTIR (neat) υ 3408, , 1384FTIR (neat) υ 3408, , 1269FTIR (neat) υ 3408, , 1109FTIR (neat) υ 3408, , 1049 ; HRMS (ESI) m/z: Calcd. For C24H21BrNO2 + : 434.0750, Found: 434.0744 (M+H + ).…”