41167-74-2Relevant articles and documents
Studies of hydrogen isotope scrambling during the dehalogenation of aromatic chloro-compounds with deuterium gas over palladium catalysts
Lockley, William J.S.,Venanzi, Niccolò A. E.,Crane, Georgie J.
, p. 531 - 552 (2020/09/22)
Catalytic dehalogenation of aromatic halides using isotopic hydrogen gas is an important strategy for labelling pharmaceuticals, biochemicals, environmental agents and so forth. To extend, improve and further understand this process, studies have been carried out on the scrambling of deuterium isotope with protium during the catalytic deuterodehalogenation of model aryl chlorides using deuterium gas and a palladium on carbon catalyst in tetrahydrofuran solution. The degree of scrambling was greatest with electron-rich chloroarene rings. The tetrahydrofuran solvent and the triethylamine base were not the source of the undesired protium; instead, it arose, substantially, from the water content of the catalyst, though other sources of protium may also be present on the catalyst. Replacement of the Pd/C catalyst with one prepared in situ by reduction of palladium trifluoroacetate with deuterium gas and dispersed upon micronised polytetrafluoroethylene led to much reduced scrambling (typically 0–6% compared with up to 40% for palladium on carbon) and to high atom% abundance, regiospecific labelling. The improved catalytic system now enables efficient polydeuteration via the dehalogenation of polyhalogenated precursors, making the procedure viable for the preparation of MS internal standards and, potentially, for high specific activity tritium labelling.
Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8-DMSO: Application to the synthesis of vernakalant
Garad, Dnyaneshwar N.,Tanpure, Subhash D.,Mhaske, Santosh B.
supporting information, p. 1008 - 1016 (2015/08/18)
Ammonium persulfate-dimethyl sulfoxide (APS-DMSO) has been developed as an efficient and new dehydrating reagent for a convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming process has been demonstrated for a practical synthesis of vernakalant.
An expeditious synthesis of imides from phthalic, maleic and succinic anhydrides and chemoselective C=C reduction of maleic amide esters
Kumar, Padam Praveen,Reddy, Y. Dathu,Kumari, Y. Bharathi,Devi, B. Rama,Dubey
, p. 392 - 398 (2014/05/06)
Phthalic, maleic and succinic anhydrides have been reacted with aromatic amines to obtain the corresponding monoacid monoamides. The latter have been each transformed into the corresponding cyclic imide derivatives by treating with SOCl2. Alternatively, anhydrides have been reacted with methanolic KOH to obtain monomethyl ester derivatives which on reaction with aromatic amines in the presence of EDC. HCl and HOBt give cyclic imide derivatives. Reaction of monoacid monoamides independently, with SOCl 2 at 0-5°C give the monoamide monoester derivatives. Treatment of monoamide monoester of malic anhydride with NaBH4 leads to the unusual reduction of C=C grouping as well as the carbonyl group of the ester group to from monoamide monoalcohol of succinic anhydride. Preparation of monoamide monoalcohol of succinic anhydride can also be achieved by chemoselective reduction of monoamide monoester of malic anhydride with Mg turnings yielding monoamide monoester of succinic anhydride followed by reduction of the latter with NaBH4.
A facile and green synthesis of N-substituted imides
Kumar, Padam Praveen,Rama Devi,Dubey
, p. 1166 - 1171 (2013/09/24)
Anhydrides 1, 6 and 10 have been reacted, independently, with aromatic primary amines 2 in solid phase by simple physical grinding of reactants with p-toluenesulphonicacid as a catalyst to yield corresponding open chain derivatives, monoacid monoamides3,7 and 11 respectively. The latter have each been transformed into the corresponding cyclic derivatives, i.e. imides 5, 9 and 13 respectively in solid phase by simple physical grinding of each with K 2CO3, alkylating agent and tetrabutylammoniumbromide as a catalyst with short reaction times. These cyclic imides can also be obtained by physical grinding of each of 3, 7 and 11 with dicyclohexylcarbodimide as a dehydrating agent in solid phase.
Aromatic-amide-derived olefins as a springboard: Isomerization-initiated palladium-catalyzed hydrogenation of olefins and reductive decarbonylation of acyl chlorides with hydrosilane
Bai, Xing-Feng,Xu, Li-Wen,Zheng, Long-Sheng,Jiang, Jian-Xiong,Lai, Guo-Qiao,Shang, Jun-Yan
supporting information; experimental part, p. 8174 - 8179 (2012/08/27)
A highly efficient catalytic protocol for the isomerization of substituted amide-derived olefins is presented that successfully uses a hydride palladium catalyst system generated from [PdCl2(PPh3)2] and HSi(OEt)3. The Z to E isomerization was carried out smoothly and resulted in geometrically pure substituted olefins. Apart from the cis-trans isomerization of double bonds, the selective reduction of terminal olefins and activated alkenes was performed with excellent functional group tolerance in the presence of an amide-derived olefin ligand, and the products were obtained in high isolated yields (up to >99 %). Furthermore, the palladium/hydrosilane system was able to promote the reductive decarbonylation of benzoyl chloride when a (Z)-olefin with an aromatic amide moiety was used as a ligand. Copyright
Substituent chemical shifts of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides
Lee, Hye Sun,Yu, Ji Sook,Lee, Chang Kiu
scheme or table, p. 711 - 715 (2010/07/05)
NMR spectra of a series of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides were examined to estimate the electronic effect of the amide and imide groups on the chemical shifts of the hydrogen and carbon nuclei of the benzene ring.
Diprotection of primary amines as N-substituted-2,5-bis[(triisopropylsilyl)oxy]pyrroles (BIPSOP)
Martin, Stephen F.,Limberakis, Chris
, p. 2617 - 2620 (2007/10/03)
Primary amines are diprotected as their 2,5-bis[(triisopropylsilyl)oxy]pyrrole derivatives (BIPSOP). This protecting group is stable to strong bases such as organolithiums and alkoxides at 0°C and to temperatures up to about 150°C. Removal may be accomplished by a mild two step sequence.
KINETICS AND MECHANISM OF THE HYDRAZINOLYSIS OF THE IMIDES OF 4-SUBSTITUTED SUCCINANILIC ACIDS IN DIMETHYLFORMAMIDE
Makurina, V. I.,Chuvurin, A. V.,Karnozhitskaya, T. M.,Chernykh, V. P.
, p. 1978 - 1980 (2007/10/02)
The thermal cyclodehydration of succinanilic acids leads to their imides.The kinetics of hydrazinolysis of the latter in DMFA are described by a second-order equation, and it was found that the process rate increases with increase in the electron-withdraw
