550-44-7Relevant articles and documents
Structural, vibrational and DFT studies on 2-chloro-1H-isoindole-1,3(2H)-dione and 2-methyl-1H-isoindole-1,3(2H)-dione
Arjunan,Saravanan,Ravindran,Mohan
, p. 642 - 649 (2009)
The Fourier transform infrared (FTIR) and FT-Raman spectra of 2-chloro-1H-isoindole-1,3(2H)-dione and 2-methyl-1H-isoindole-1,3(2H)-dione have been measured in the range of 4000-400 and 4000-100 cm-1, respectively. Complete vibrational assignment and analysis of the fundamental modes of the compounds were performed using the observed FTIR and FT-Raman data. The geometry was optimised without any symmetry constraints using the DFT/B3LYP method with 6-31G(d,p) and 6-311++G(d,p) basis sets. The vibrational frequencies determined experimentally are compared with those obtained theoretically from DFT gradient calculations employing the B3LYP/6-31G(d,p) and B3LYP/6-311++G(d,p) methods for the optimised geometry of the compounds. The structural parameters and normal modes of vibration obtained from DFT method are in good agreement with the experimental data. The force fields obtained from DFT method were utilised and the potential energy distributions of all the fundamental vibrations of the compounds were calculated.
A convenient method of N-methylphthalimide synthesis
Vasilevskaya,Yakovleva,Kobrin
, p. 2463 - 2465 (1995)
We suggest a convenient method to obtain N-methylphthalimide with a high yield in the reaction of phthalic anhydride with aqueous methylamine.
Base-controlled product switch in the ruthenium-catalyzed protodecarbonylation of phthalimides: A mechanistic study
D'Alterio, Massimo Christian,Yuan, Yu-Chao,Bruneau, Christian,Talarico, Giovanni,Gramage-Doria, Rafael,Poater, Albert
, p. 180 - 186 (2020)
The whole reaction mechanism of the ruthenium-catalyzed protodecarbonylation of N-substituted phthalimides into secondary amides was unravelled by a combined experimental and theoretical study. The chemoselectivity of the reaction, which is catalyzed by para-cymene coordinated Ru(ii) species all over the catalytic cycle, is exclusively controlled by the unique roles of the bases. Meanwhile, in the presence of K2CO3 or KOH at high temperatures, the same product (benzamide) is mainly formed, whereas at low temperatures, KOH led to an unexpected side-product (phthalamic acid) and no reactivity was observed with K2CO3. The non-covalent interactions between the potassium cations and the different carbonyl groups in the molecules are key to providing a thermodynamically favourable pathway with energetically accessible transition states. The unexpected formation of carbon dioxide (CO2) in the course of the reaction originates from the phthalimide substrate and the base K2CO3 in two different elementary steps, respectively.
Second-generation tags for fluorous chemistry exemplified with a new fluorous Mitsunobu reagent
Chu, Qianli,Henry, Christopher,Curran, Dennis P.
, p. 2453 - 2456 (2008)
(Chemical Equation Presented) A new fluorous DEAD reagent bearing two perfluoro-tert-butyloxy groups with propylene spacers shows excellent promise for use in fluorous Mitsunobu reactions. Pure target products were obtained in good yields after removing fluorous byproducts by FSPE. The new reagent serves as a prototype for a greener second generation of fluorous reagents bearing tags that are not expected to degrade in the environment to compounds that are highly persistent or that bioaccumulate in higher organisms.
Preparation of alkylated compounds using the trialkylphosphate
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Paragraph 0184-0185; 0208, (2021/11/02)
[Problem] trialkylphosphate strong base used reaction agent, a carboxylic acid, a ketone, an aldehyde, amine, amide, thiol, ester or Grignard reagent to a variety of substrates, and/or high efficiency to generate a highly stereoselective alkylation reaction, the alkylated compounds capable of producing new means. [Solution] was used as the alkylating agent in the alkylation of compound trialkylphosphate, strongly basic reaction production use. [Drawing] no
Preparation method of N - alkyl -4 -nitrophthalimide
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Paragraph 0040-0041; 0053-0053; 0055-0056, (2021/10/27)
The invention discloses a preparation method of N - alkyl -4 -nitrophthalimide, which comprises the following steps of 1) mixing phthalic anhydride, alkyl aldehyde and inorganic amine, reacting under the action of hydrogen, cooling and crystallizing, and drying to obtain N -alkyl phthalimide. Step 2) The 1 alkylphthalimide obtained in step N -) is subjected to nitration reaction, and the product is purified and dried to obtain the N -alkyl -4 -nitrophthalimide. The alkyl aldehyde in step 1) is preferably an alkyl aldehyde of carbon 1 - 4. The preparation method has the advantages of wide raw material source, low price, simple process, easiness in large-scale production and the like. Through one-step synthesis, the reaction efficiency is high, the device is simple and easy to operate, and green and environment-friendly.
Copper-promoted direct amidation of isoindolinone scaffolds by sodium persulfate
Lai, Huifang,Lin, Jin,Xu, Jiexin,Zha, Daijun
supporting information, p. 7621 - 7626 (2021/09/22)
Isoindolinones are ubiquitous structural motifs in natural products and pharmaceuticals. Establishing an efficient method for structural modification of isoindolinones could significantly facilitate new drug development. Herein, we describe copper-promoted direct amidation of isoindolinone scaffolds mediated by sodium persulfate. The method exhibits mild reaction conditions and high site-selectivity, and enables the structural modification of the drug indobufen ester with various amides with yields of 49 to 98%. It is also gram-scalable. Additionally, the reaction mechanism appears to involve a radical and a carbocationic pathway.
Regio- And Stereoselective (S N2) N -, O -, C - And S -Alkylation Using Trialkyl Phosphates
Banerjee, Amit,Hattori, Tomohiro,Yamamoto, Hisashi
, (2021/06/16)
Bimolecular nucleophilic substitution (S N 2) is one of the most well-known fundamental reactions in organic chemistry to generate new molecules from two molecules. In principle, a nucleophile attacks from the back side of an alkylating agent having a suitable leaving group, most commonly a halide. However, alkyl halides are expensive, very harmful, toxic and not so stable, which makes them problematic for laboratory use. In contrast, trialkyl phosphates are inexpensive, readily accessible and stable at room temperature, under air, and are easy to handle, but rarely used as alkylating agents in organic synthesis. Here, we describe a mild, straightforward and powerful method for nucleophilic alkylation of various N -, O -, C - and S -nucleophiles using readily available trialkyl phosphates. The reaction proceeds smoothly in excellent yield, and quantitative yield in many cases, and covers a wide range of substrates. Further, the rare stereoselective transfer of secondary alkyl groups has been achieved with inversion of configuration of chiral centers (up to 98% ee).
Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams
Bai, Ya,Shi, Lingling,Zheng, Lianyou,Ning, Shulin,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao
supporting information, p. 2298 - 2302 (2021/04/05)
An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.
Preparation method of N-alkyl phthalimide
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Paragraph 0031-0034, (2021/03/13)
The invention discloses a preparation method of N-alkyl phthalimide. The method comprises the steps: taking phthalic anhydride as a raw material, taking an aqueous solution of alkylamine as an imidization reagent ( no other reagents do not need to be added), and directly synthesizing the N-alkyl phthalimide, wherein the yield is high (96% or above), and the purity is high (99% or above). The preparation method is loose in reaction condition, simple in step and easy to implement; no organic solvent is needed, no other substances are discharged except water, and the method is green, free of pollution and suitable for industrial production.
