Scheme 1.
Syntheses of 3-substituted quinolin-2-amine analogues. Reagents: (i) butyl iodide, K2CO3, DMSO; (ii) m-CPBA, CHCl3; (iii) (a) benzoyl isocyanate, CH2Cl2; (b) NaOMe, MeOH; (iv) H2, Pt/C, EtOH; (v) NH3, MeOH; (vi) butylSH, NaH, DMSO; (vii) Pd(PPh3)4, RB(OH)2, K2CO3, 1,4-dioxane, for 14f: Pd(PPh3)4, CuI, 1-pentyne, Et3N:CH3CN (1:3).