Use iTunes' Up Next function with an API

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iTunes has no public API but the scripting bridge

you could use Applesript UI Scripting I’d wager — but that would be very fragile

you can also simulate a keypress then:
That less fragile than scripting the visible interface (IMO):

TADA — YAY — a ‘ready’ script that will add songs selected to UpNext ::

tell application "AppleScript Utility"
    set GUI Scripting enabled to true
end tell

tell application "iTunes"
    --get the song
    set l to playlist "Purchased"
    set t to item 5 of tracks of l

    --focus it in list
    reveal t

    --show window
end tell

tell application "System Events"
    -- option enter
    delay 1
    key down option
    delay 1
    key code 36
    key up option

    -- Click the “Play Song” button in the annoying dialog.
    set w to null
        set w to window "Add to Up Next" of application process "iTunes"
    end try
    if w is not null then
        set b to UI element "Play Song" of w
        click b
    end if
end tell