Abstract Enal and ynal‐derived α,β‐unsaturated acylazoliums under N‐heterocyclic carbene (NHC) catalysis have been applied for annulations with indolin‐3‐ones. The two reactions offer a direct and efficient access to functionalized 3,4‐dihydropyrano[3,2‐b]indol‐2‐ones in moderate to high yields, which may provide promising candidates for drug discovery.