Diversity-oriented approach to 1,2-dihydroisoquinolin-3(4H)-imines viacopper(i)-catalyzed reaction of (E)-2-ethynylphenylchalcone, sulfonyl azide and amine

Abstract

A three-component reaction of (E)-2-ethynylphenylchalcone, sulfonyl azide, and amine catalyzed by copper(I) chloride (5 mol%), in the presence of triethylamine, under mild conditions is described. This transformation proceeds efficiently to generate 1,2-dihydroisoquinolin-3(4H)-imines in good to excellent yields.

Unexpected Catalytic Reactions of Silyl-Protected Enol Diazoacetates with Nitrile Oxides That Form 5-Arylaminofuran-2(3H)-one-4-carboxylates

“…11 They are accessible via azide cycloaddition with acetylenes (“click” chemistry), 12 the isocyanide-Nef-Perkow reaction sequence, 13 from ynamides by Pd(0)-catalyzed N-to-C allyl transfer, 14 and even by pulsed pyrolysis of isoxazole. 15 Their structural diversity is dependent on the methods for their formation, and structure 8 is unique.…”

CuI/I2‐Mediated Intramolecular Oxidative Cyclization Reaction of N‐(2‐pyridyl)amidines by the Direct Double C−H Functionalization of a C(sp3)−H Bond

“…Delightedly, an investigation found that N ‐(2‐pyridyl)amidines could be afforded by the efficient reaction between 2‐aminopyridines, terminal alkynes, and sulfonyl azides by using a copper salt and base. The reaction operated through ketenimine intermediates, and the transformation has been extensively reported by Chang,– Wang, Lee, Wu, Yi and their respective co‐workers under extremely mild conditions. However, to our surprise, according to Chang's procedure, in addition to a complex unidentified product, the desired 2‐amino analogs ( A ) from N ‐(2‐pyridyl)amidines were not observed under the same conditions.…”

Copper‐Catalysed Multicomponent Syntheses of Heterocycles

“…An efficient Copper(I) chloride catalysed three‐component method for the synthesis of 1,2‐dihydroisoquinolin‐3(4 H )‐imines from ( E )‐2‐ethynylphenylchalcone, amine and sulfonyl azide was reported . The optimized reaction conditions include CuCl (5 mol%) as catalyst, TEA (1.5 equiv.)…”