Specific intramolecular aromatic C H insertion of diazosulfonamides

Huang, Peipei; Yang, Zhanhui; Xu, Jiaxi

doi:10.1016/j.tet.2017.04.056

Cited by 17 publications

(30 citation statements)

References 32 publications

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“…However, this rhodium-mediated catalytic system turned out to be ineffective for N -alkyl- N -aryl diazosulfonamide substrates. Afterwards, Xu and Yang et al addressed this problem with the use of an inexpensive copper-catalyst in reflux toluene ( Scheme 8 b) [ 70 ].…”

Section: Transition Metal-catalyzed Benzosultam Synthesismentioning

confidence: 99%

Recent Advances in Catalytic Synthesis of Benzosultams

Zhao

2020

Molecules

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Benzosultams represent one category of multi-heteroatom heterocyclic scaffolds, which have been frequently found in pharmaceuticals, agricultural agents, and chiral catalysts. Given the diversely significant functions of these compounds in organic and medicinal chemistry, great efforts have been made to develop novel catalytic systems for the efficient construction of benzosultam motifs over the past decades. Herein, in this review, we mainly summarize the recent advances in the field of catalytic synthesis of benzosultams from 2017 to August of 2020, with an emphasis on the scopes and mechanisms of representative reactions.

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Section: Transition Metal-catalyzed Benzosultam Synthesismentioning

confidence: 99%

Recent Advances in Catalytic Synthesis of Benzosultams

Zhao

2020

Molecules

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“…[6,14] Fluorine-based prophylactic agents, besides reducing corrosion resistance, increase surface roughness and friction in orthodontic archwires. [25] Curasept is a moderate medium because it is less acid than Listerine, and slightly more acidic than Gengigel and has a higher fluoride content. It has been reported previously that the effect of chlorhexidine on surface roughness is not significant.…”

Section: Corrosion Ratecomparison Of the Effect Of The Same Media Omentioning

confidence: 99%

Effect of oral antiseptics on the corrosion stability of nickel‐titanium orthodontic alloys

Mlinarić

Kanižaj

Žuljević

et al. 2017

Materials & Corrosion

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The aim was to explore the influence of the interaction of oral antiseptics and various coatings on the corrosion behavior of nickel‐titanium (NiTi) orthodontic alloys. NiTi archwires with uncoated, rhodium‐coated, and nitride‐coated surface were exposed to artificial saliva pH 4.8 at the temperature of 37 °C, and to saliva with the addition of three commercial oral antiseptics (Curaspet, Gengigel, and Listerine). Electrochemical impedance spectroscopy and cyclic polarization were performed. Released nickel and titanium ions after a period of 7 days were measured by inductively coupled optical emission spectroscopy. Results demonstrate that the rate and degree of corrosion mainly increase with the addition of antiseptics. Electrochemical impedance spectroscopy indicates the biggest corrosion resistance in Gengigel. Rhodium‐coated NiTi demonstrates higher corrosion rate in saliva and in all antiseptics than uncoated and nitride‐coated NiTi. The highest tendency toward localized corrosion is seen in rhodium‐coated NiTi in all media, and least in nitride‐coated NiTi. The release of titanium ions mainly supports findings of general corrosion rate. These results indicate that both antiseptics and coating modify corrosion.

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“…Recently, we put much attention to the reactivity of different diazosulfonamides (Scheme 1b) [24,25], and realized the rhodium- and copper-catalyzed intramolecular aromatic 1,5-C-H insertion of N,N -diaryl diazomethanesulfonamides with the ethoxycarbonyl group (ethyl 2-( N,N -diarylsulfamoyl)-2-diazoacetates) to prepare ethyl 1-aryl-1,3-dihydrobenzo[ c ]isothiazole-3-carboxylate 2,2-dioxides ( N -aryl-3-ethoxycarbonyl benzo-γ-sultams) (R = OEt, Scheme 1b) [24]. We also achieved the copper-catalyzed intramolecularly aromatic 1,5-C-H insertion of N -alkyl- N -aryl diazomethanesulfonamides 1 with the acetyl and benzoyl groups to synthesize 1-alkyl-3-acetyl/benzoyl-2,2-dioxido-1,3-dihydrobenzo[ c ]isothiazoles (R = Me, Ph, Scheme 1b) [25]. For the N -alkyldiazomethanesulfonamides with acetyl, benzoyl, and ethoxycarbonyl groups, the aliphatic C-H insertions, including 1,4-, 1,5-, and 1,6-insertions, of the N -alkyl groups on the sulfonamide moiety were not observed [24,25].…”

Section: Introductionmentioning

confidence: 99%

“…We also achieved the copper-catalyzed intramolecularly aromatic 1,5-C-H insertion of N -alkyl- N -aryl diazomethanesulfonamides 1 with the acetyl and benzoyl groups to synthesize 1-alkyl-3-acetyl/benzoyl-2,2-dioxido-1,3-dihydrobenzo[ c ]isothiazoles (R = Me, Ph, Scheme 1b) [25]. For the N -alkyldiazomethanesulfonamides with acetyl, benzoyl, and ethoxycarbonyl groups, the aliphatic C-H insertions, including 1,4-, 1,5-, and 1,6-insertions, of the N -alkyl groups on the sulfonamide moiety were not observed [24,25]. Compared with diazoacetamides, only limited investigations on the reactivity and chemoselectivity on diazosulfonamides were conducted [24,25].…”

Section: Introductionmentioning

confidence: 99%

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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Specific intramolecular aromatic C H insertion of diazosulfonamides

Cited by 17 publications

References 32 publications

Recent Advances in Catalytic Synthesis of Benzosultams

Recent Advances in Catalytic Synthesis of Benzosultams

Effect of oral antiseptics on the corrosion stability of nickel‐titanium orthodontic alloys

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

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