The tricyclic bisamidines 1 and 2 both have syn-periplanar donor sites but exhibit significantly different coordination chemistry towards transition metals. For example, the Ag(I) complex of 1 features three coordination mode while 2 only chelates Ag(I). A new general synthesis of a C₂-symmetric tricyclic bisamidine 3 has been developed and is illustrated by the synthesis of 3 (R = ⁱPr) which was previously reported by Casey et al. in 2004.