A series of spiro[indoline‐3,3'‐pyrrolizin]‐2'‐yl)‐4‐phenylquinoline‐3‐carboxylate 6 from 2‐amino‐5‐chlorobenzhydrol 1, benzyl alcohols 3, and methyl or ethyl acetoacetate 2 is reported by the Cu(OAc)2, TEMPO catalyzed dehydrogenative Friedlander annulation/sp3–CH‐functionalization/regioselective 1,3‐ dipolar cyclo‐ addition. Likewise, chimanine A analogues 7 were obtained using a similar strategy in DES (Deep Eutectic Solvents) as a reaction medium in excellent yields.
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