The socratic dialogues and enlightenment debates are generally taken up by engaged participants (else the dialogues would be quite short eh?) and aim at the idea of revealing truth through questions, or tackling fundamentally interesting ideas.
The dialogues in HPMOR are most often "you're so, so wrong because your mind is defective and clouded by this list of 30 erroneous thinking patterns. Let me elaborate for 10 minutes about why you're a blind fool and I'm a genius who sees the truth".
The pattern is very different and I think characterising what's done in HPMOR, and what's in greek or enlightenment philosophy is a bad idea.
There are good rationalist writers but Yudkowsky is not the one to look at.