AGI and AMI is what you need for this.

AMI is for originating the call between extensions
AGI for playing file of your choice.

Both these APIs are well documented

http://www.voip-info.org/wiki/view/Asterisk+AGI

http://www.voip-info.org/wiki/view/Asterisk+manager+API

-- 
Thanks & Regards,
Godson Gera
Asterisk Consultant India <http://godson.in>
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