You could in theory do this using a CSV Import, by creating 300 issues and associating a new user to each issue uploaded. It's not an ideal method though, and will likely require some updates to be made to those users after creation.
I'd suggest using an app to achieve this - such as Bulk User Creator for Jira - or if you're using Atlassian Crowd, you can upload users from a CSV here also - see this page for details.
Ste
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