Vladimir Putin has complained that he has received neither an apology from Turkey nor an offer “to make up for the damages” following the downing of a Russian warplane.
The Russian president also said Turkey has not given any assurances that “the culprits of this crime” will be punished.
Previously warm relations between the two countries have soured after Turkey shot down a Russian Su-24 on a bombing mission near the Syria border on Tuesday.
Russia insisted that its plane never violated the Turkish airspace as Turkey claimed.
Speaking at the Kremlin, Mr Putin said he regretted the fact that relations between Turkey and Russia have been driven into a stalemate.
Turkish president Recep Tayyip Erdogan has hit back at Russia, accusing it of using its fight against Islamic State in Syria as a pretext to target opposition groups in a bid to strengthen Syrian president Bashar Assad.
Without naming Russia openly, Mr Erdogan also challenged the country to prove its accusation that Turkey is buying oil and gas from IS, and called the claims “shameful”.
He said Turkey was the country leading the most serious fight against IS, saying it had detained thousands of militants over the past few years.
Mr Erdogan added that Turkey had not specifically targeted Russia when it shot down the plane, saying it was “an automatic response” in line with its rules of engagement.
He said: “Faced with the same violation today, Turkey would give the same response.”