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The Permian period
During the Permian, the land vertebrates grew to large sizes, the ancestors of some families of coniferous trees began to dominate the forests, and some small reptiles learned to glide from tree to tree. At the end of the period, the most devastating mass extinction event in Earth’s history happened, wiping out most of the life on land and in the oceans, and setting the stage for the next period, and the rise of the dinosaurs.
Here are a couple of articles about the Permian, and the mass extinction that ended it.