1350 or 1351 – Ivan Shishman was born By 1355 – Proclaimed heir to the throne and co-emperor 17 February 1371 – Succeeds his father as Emperor of Bulgaria in Tarnovo 1373 – Becomes Ottoman vassal in return for some previously conquered lands 1378 – Issues the Rila Charter 1385 – Fall of Sofia 1384 to 1386 – War against Wallachia 1388 – The Ottomans invade eastern Bulgaria and conquer a number of towns 17 July 1393 – Fall of Tarnovo 3 June 1395 – The Ottomans capture Nikopol and Ivan Shishman is executed