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. © 2020 Wiley-VCH GmbH