Copper(II)-Mediated ortho-Selective C(sp2)–H Tandem Alkynylation/Annulation and ortho-Hydroxylation of Anilides with 2‑Aminophenyl‑1H‑pyrazole as a Directing Group

2-Aminophenyl-1H-pyrazole has been identified as a viable directing group to promote copper­(II)-mediated ortho-selective sp2 C–H bond tandem alkynylation/annulation of anilides with terminal alkynes to offer arylmethylene isoindolinones. Meanwhile, copper­(II)-mediated ortho-selective sp2 C–H hydroxylation of anilides has also been optimized as the major reaction pathway by using Cu­(OAc)2 as the promoter and 1,1,3,3-tetramethylguanidine as an organic base. Recovery of the directing group was achieved by hydrazinolysis for arylmethylene isoindolinones and basic hydrolysis for the hydroxylation products.