A concise method for the synthesis of heterocycle-fused naphthoquinones such as naphtho [2, 3-b]-furan-4, 9-dione, 1H-benz [f] indole-4, 9-dione, and naphtho [2, 3-b] thiophene-4, 9- dione was developed. This method employed Sonogashira coupling and tandem addition- elimination/intramolecular cyclization, and it enabled the preparation of versatile heterocycle- fused naphthoquinones from one substrate.