Vladimir Putin escalated his confrontation with Turkish President Recep Tayyip Erdogan over the downing of a Russian bomber, saying relations are beyond repair while declaring Syria a no-fly zone for Turkish military aircraft.

"Turkey used to violate Syrian airspace all the time," Putin told reporters Thursday. "Let them try and fly there now" that Russia's most advanced air-defense system is covering the whole country, he said. Russia is taking part in international talks Friday on how to end Syria's more than four-year civil war.

President Vladimir Putin speaks during his annual press conference.

Photographer: Natalia Kolesnikova/AFP via Getty Images

The Nov. 24 shoot-down, the first by a NATO member of a Russian aircraft in decades, came less than two months after Putin joined the Syrian war on the side of Bashar al-Assad. That has complicated efforts by the U.S. and its allies, which have been bombing jihadist groups for almost two years, to end a conflict that's killed a quarter million people and sparked Europe's worst migrant crisis since World War II.

Putin, speaking during his annual press conference in Moscow, reiterated his refusal to allow outside forces to decide Syria's fate, but he said Russia and the U.S. are moving closer to an agreement on how to end the war and form a new government. Russia's plan for Syria, which is wedged between Turkey and Iraq, is generally in line with a UN resolution drafted by the U.S. that will be discussed at talks in New York on Friday, he said.