133387-33-4Relevant academic research and scientific papers
Tert-amino effect-promoted rearrangement of aryl isothiocyanate: A versatile approach to benzimidazothiazepines and benzimidazothioethers
Geng, Xinyu,Liu, Siyuan,Qu, Jingping,Wang, Baomin,Wang, Wenyao
, p. 12635 - 12643 (2020/11/09)
A general and practical approach to benzimidazothiazepine and benzimidazothioether derivatives via an intramolecular nucleophilic addition/ring expansion rearrangement of aryl isothiocyanates promoted by the tert-amino effect has been developed. This reaction is catalyzed by low-cost camphorsulfonic acid and tolerates a broad substrate scope with complete atom economy. Structurally intriguing benzimidazothiazepine and benzimidazothioether products could be easily obtained by a simple operation in good to excellent yield (up to 98%).
Regular trends in nucleophilic substitutions in 2-alkylamino-4- chloronitrobenzenes
Zotova,Kushakova,Kuznetsov,Rodin,Garabadzhiu
, p. 214 - 217 (2007/10/03)
The effect of substituents in position 2 on the reactivity of 2-alkylamino-4-chloronitrobenzenes in nucleophilic substitution by N-nucleophiles of various character was studied. 2005 Pleiades Publishing, Inc.
Reaction of Mono-, Di-, and Trichloronitrobenzenes with N-Methyl Substituted Cyclic Tertiary Amines under High Pressure
Ibata, Toshikazu,Shang, Muhong,Demura, Tetsuo
, p. 2717 - 2726 (2007/10/03)
The reactions of mono-, di-, and trichloronitrobenzenes with 1-methylpyrrolidine under high pressure gave products of demethylation and ring-opening through a quaternary pyrrolidinium chloride intermediate formed by the SNAr reaction.On the other hand, the reactions with 1-methylpiperidine and 4-methylmorpholine gave only demethylation products.The selectivities of the resctions of 1-methylpyrrolidine with these chloronitrobenzenes were found to be effected by the neighboring substituent to the pyrrolidinium group.
Nucleophilic Substitution Reaction of Aromatic Chlorides with Cyclic Tertiary Amines under High Pressure
Ibata, Toshikazu,Shang, Muhong,Demura, Tetsuo
, p. 359 - 362 (2007/10/02)
The reaction of p-chloronitrobenzene with N-methylpyrrolidine under high pressure gave demethylation product and ring opening products through quaternary ammonium chloride intermediate formed by the SNAr reaction.On the other hand, the reactions with N-methylpiperidine and N-methylmorpholine gave only demethylation products.The reactions of o-chloronitrobenzene and 2,4-dichloronitrobenzene with above amines gave similar results.
Aromatic Nucleophilic Substitution of Halobenzenes with Amines under High Pressure
Ibata, Toshikazu,Isogami, Yasushi,Toyoda, Jiro
, p. 42 - 49 (2007/10/02)
The nucleophilic substitution reactions of aromatic halides having electron-attracting groups on ortho or para position with various primary and secondary amines were accelerated by high pressure to give the corresponding N-substituted anilines in high yields.The bulkiness of amines affects its reactivity to lower the yields of the products.Although the secondary amines are usually less reactive than primary amines, cyclic secondary amines such as morpholine, piperidine, and pyrrolidine were found very reactive. 1,4-Diazabicyclooctane and quinuclidine gave N-quarternary ammonium halides in high yields in contrast to the low reactivity of acyclic tertiary amines.Dichloro- and trichloro-nitrobenzenes also react with diethylamine, pyrrolidine, and morpholine to give mono-, di-, and trisubstitution products depending upon the amount of amine and the position of nitro group in these chlorides.
