Heteroaromatic nucleophilic substitution
Heteroatoms activate the para and ortho positions for substituion.
SMARTS: [c;!$(c1ccccc1);$(c1[n,c]c[n,c]c[n,c]1):1][Cl,F].[N;$(NC);!$(N=*);!$([N-]);!$(N#*);!$([ND3]);!$([ND4]);!$(N[c,O]);!$(N[C,S]=[S,O,N]):2]>>[c:1][N:2]
Conditions
Reactant 1: pyridine, pyrimidine, triazine.
Reactant 2: primary or secondary halide.
A: C, N. R1, R2: aryl. X: Cl, F.
References
Schuerer et. al., J chem Inf Model, 2005, 45, 239-248.
Other sources
Organic chemistry