Chemospecific synthesis of 2-acetoxyindole-3-carbonitriles catalyzed by Cu(acac)2

Mo, Shanyan; Tu, Jianzhuo; Xu, Jiaxi

doi:10.1007/s11172-016-1509-6

Cited by 3 publications

(2 citation statements)

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“…Although the aliphatic carbene 1,4-C-H insertion of diazoamides generally occurred and was sensitive to the acyl groups [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15], it appeared quite different in our attempted acyl diazo- N -methylmethanesulfonamides [25] and 2-diazo-2-( N -benzyl- N -butylsulfamoyl)acetamides 1c , d , possibly because of the subtle changes in conformation or the bond length of diazomethanesulfonamides, as Doyle and coworkers mentioned [3].…”

Section: Resultsmentioning

confidence: 99%

“…The transition-metal-catalyzed intramolecularly aliphatic and aromatic C-H insertions of diazo amides provide important transformations to efficiently synthesize nitrogen-containing heterocycles with the new C-C bond formation [1,2,3,4]. The reactivity of diazoamides has been well studied (Scheme 1a), affording β-lactams ( I ) [5,6,7,8,9], γ-lactams ( II ) [5,6,7,8,9], indolin-2-ones ( III ) [10,11,12,13,14,15], 1,4-dihydroisoquinolin-3(2 H )-ones ( IV ), Buchner products ( V ), and cyclopropanation products ( VI ) [16,17,18,19,20,21] (Scheme 1a) and a series of exquisite reactions has been established to construct complex and useful structures, such as biological and natural products [22,23].…”

Section: Introductionmentioning

confidence: 99%

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Intramolecular Carbene C-H Insertion Reactions of 2-Diazo-2-sulfamoylacetamides

et al. 2019

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The intramolecular C-H insertions of carbenes derived from 2-diazo-2-sulfamoylacetamides were studied. 2-Diazo-2-sulfamoylacetamides were first prepared from chloroacetyl chloride and secondary amines through acylation followed by sequential treatments with sodium sulfite, phosphorus oxychloride, secondary amines, and 4-nitrobenzenesulfonyl azide. The results indicate that: (1) 2-diazo-N,N-dimethyl-2-(N,N-diphenylsulfamoyl)acetamide can take the formal aromatic 1,5-C-H insertion in its N-phenylsulfonamide moiety to afford the corresponding 1,3-dihydrobenzo[c]isothiazole-3-carboxamide 2,2-dioxide derivative; (2) no aliphatic C-H insertions occur for 2-diazo-2-(N,N-dialkylsulfamoyl)acetamides; and (3) for 2-diazo-N-phenyl-2-(N-phenylsulfamoyl)acetamides, the formal aromatic 1,5-C-H insertion in the N-phenylacetamide moiety is favorable to afford the corresponding 3-sulfamoylindolin-2-one derivatives as sole or major products. The intramolecular competitive aromatic 1,5-C-H insertion reactions of 2-diazo-2-sulfamoylacetamides with aryl groups on both amide and sulfonamide groups reveal that the N-aryl substituents on acetamide are more active than those on sulfonamide. The chemoselectivity is controlled by electronic effect of the aryl group.

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