He resisted the spread of the Ottomans in Anatolia: Who is Alaattin Ali of Karaman?

( ? -1398) Karaman bey. He resisted the spread of the Ottomans in Anatolia and was killed by Yıldırım Bayezid. He is the son of Karaman Bey Halil Bey. Little is known about his life before he became the ruler of Karaman. After the death of his father Halil Bey, the Karaman Principality was the scene of long struggles for the throne. It is thought that Alaeddin Ali Bey was the ruler of Karaman towards the end of the 1350s. In some sources, the date of accession to the throne of Alaeddin Ali Bey is shown as 1361.

Alaeddin Ali of Karaman (aka Damat Ali Bey) was a bey of Karaman Beylik, a Turkish principality in Anatolia in the 14th century. Like most other Karaman beys, Ali Bey was a rival of the rising Ottoman Empire, and the two principalities engaged in chronic wars against one another.

Alaeddin Ali Bey had good relations with the Ottoman Principality, which was the most powerful of the Turkish principalities in the conflict in Anatolia, helped Orhan Bey's Rumelian expedition, and married Melek Sultan, the daughter of Murad I. However, in the face of the Ottomans trying to increase their power in Anatolia by spreading to Rumelia, he tried to prevent this strengthening with alliances between principalities.

Karaman, historically known as Laranda, is a city in south central Turkey, located in Central Anatolia, north of the Taurus Mountains, about 100 km (62 mi) south of Konya. It is the capital district of the Karaman Province. The town owes its name to Karaman Bey, who was one of the rulers of the Karamanid dynasty. 

In 1359, he fought together with these local principalities against the attempt of the Kingdom of Cyprus to dominate the southern coasts of Anatolia. Skirmishes in this region continued at various intervals until 1367. On this date, Alaeddin Ali Bey besieged Gorigos (in Icel) with a large army. Although the siege did not succeed, the Cypriots were forced to retreat.

The Karamanids, also known as the Emirate of Karaman and Beylik of Karaman, was one of the Anatolian beyliks, centered in South-Central Anatolia around the present-day Karaman Province. From the middle 1300s until its fall in 1487, the Karamanid dynasty was one of the most powerful beyliks in Anatolia.

The first encounter between Alaeddin Ali Bey and Murad I took place in 1361. Alaeddin Ali Bey, who made an alliance with Ankara Akhis and Eretnaoğlu Mehmed Bey, came to Bursa and Iznik, but could not reach an important result. Later, Alaeddin Ali Bey, who went to war with Kadı Burhaneddin, who was holding Sivas, captured Kayseri for a while but had to retreat due to the counterattack of Kadı Burhaneddin. Upon this attitude of Alaeddin Ali Bey, who attacked Yalvaç, Karaağaç, and Seydişehir, which the Ottomans bought from Hamidoğulları, and captured Beyşehir, while I Murad was at war in Rumeli, I Murad declared war on the Karamanoğulları. Alaeddin Ali Bey, who was defeated by the forces of Timurtaş Pasha in the war near Konya, withdrew to Konya, and upon the siege of the city, his wife sent Melek Sultan, daughter of Murad I, as an intermediary to ask for peace. Peace was made on the condition that the Karamanids return the lands they had captured.

Alaeddin Ali Bey, who started the war again after the death of Murad I in Kosovo in 1389, had to make peace by giving back the places he had captured after Bayezid I besieged Konya. Continuing to clash with Kadı Burhaneddin between 1390-1394, Alaeddin Ali declared his loyalty to Timur with his entry into Anatolia on this date. While Bayezid I was on the Wallachian campaign, the Karamanlides raided Ankara and took Anatolian Beylerbeyi Sarı Timurtaş Pasha captive, and took him to Konya.

Bayezid marched on Konya again after this event. Although Alaeddin Ali Bey released Timurtaş Pasha to prevent the war, Bayezid, who wanted to solve the Anatolian principalities problem before facing the approaching Timur threat, continued the campaign and besieged Konya for the second time in 1398. After a ten-day siege, the townspeople agreed to surrender. Alaeddin Ali Bey had to meet with Bayezid I in Konya and was defeated, captured, and killed because he did not receive any support from the people.