4494-54-6Relevant academic research and scientific papers
The photochemistry of N-phenyl phthalonimide: Formation of substituted dihydroisocoumarins in the presence of tertiary amines
Suau, Rafael,De Inestrosa Villatoro, Ezequiel P.
, p. 6293 - 6302 (1995)
N-Phenyl phthalimide and 3,4-Dihydroisocoumarins were obtained by irradiation of N-phenyl phthalonimide in the presence of tertiary amines. The δ-lactone structure was demonstrated via an alternative synthesis that gave the isomeric γ-lactone as well. The key steps of the photoreaction, and the role of the amine, oxygen and several potential intermediates are discussed.
Synthesis of imides via palladium-catalyzed three-component coupling of aryl halides, isocyanides and carboxylic acids
Wang, Bo,He, Dan,Ren, Beige,Yao, Tuanli
supporting information, p. 900 - 903 (2020/02/03)
A palladium-catalyzed three-component synthesis of acyclic imides from feedstock aryl halides, carboxylic acids and isocyanides through the intermediacy of isoimides has been developed. The key to the success of this approach was controlled isocyanide slow addition and organic/aqueous biphasic conditions. This transition-metal-catalyzed approach features readily available starting materials, atom- and step-economy, good functional group compatibility and gram-scale synthetic capability. Utilization of this new method is illustrated in the late-stage functionalization of drugs Carprofen, Loxoprofen and Flurbiprofen. This strategy has also been successfully applied in the synthesis of cyclic imides including phthalimide, homophthalimide, and 2H-2-benzazepine-1,3-dione derivatives.
Enantioselective synthesis of isoquinoline-1,3(2: H,4 H)-dione derivatives via a chiral phosphoric acid catalyzed aza-Friedel-Crafts reaction
You, Yong,Lu, Wen-Ya,Xie, Ke-Xin,Zhao, Jian-Qiang,Wang, Zhen-Hua,Yuan, Wei-Cheng
supporting information, p. 8478 - 8481 (2019/07/22)
A highly enantioselective aza-Friedel-Crafts reaction of structurally new ketimines with indoles and pyrrole is developed by using a chiral phosphoric acid as the catalyst. This protocol enables the first enantioselective synthesis of isoquinoline-1,3(2H,
RhII-Catalyzed Cycloaddition of α-Diazo Homophthalimides and Nitriles Delivers Oxazolo[5,4-c]isoquinolin-5(4H)-one Scaffold
Kantin, Grigory,Dar'in, Dmitry,Krasavin, Mikhail
supporting information, p. 4857 - 4859 (2018/09/14)
Homophthalimides underwent facile diazo transfer reactions and the resulting diazo homophthalimides entered cycloaddition reactions with nitriles catalyzed by Rh2(OAc)4. The latter reaction represents the first example of 1,3-oxazole
Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives
Yuan, Yu-Chao,Kamaraj, Raghu,Bruneau, Christian,Labasque, Thierry,Roisnel, Thierry,Gramage-Doria, Rafael
, p. 6404 - 6407 (2017/12/08)
The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.
Synthesis of oxindole from acetanilide via Ir(iii)-catalyzed C-H carbenoid functionalization
Patel, Pitambar,Borah, Gongutri
supporting information, p. 443 - 446 (2017/01/03)
Herein we disclose the first report on the synthesis of oxindole derivatives from acetanilide via Ir(iii)-catalyzed intermolecular C-H functionalization with diazotized Meldrum's acid. A broad range of substituted anilides were found to react smoothly under the Ir(iii)-catalytic system to afford the corresponding N-protected oxindoles. The N-protecting groups, such as Ac, Bz or Piv, can be easily removed to furnish the oxindole. Various synthetic applications of the synthesized oxindole were also demonstrated.
2-Arylacetamides as Versatile Precursors for 3-Aminoisocoumarin and Homophthalimide Derivatives: Palladium-Catalyzed Cascade Double Carbonylation Reactions
Frutos-Pedre?o, Roberto,García-López, José-Antonio
, p. 2692 - 2700 (2016/08/30)
The synthesis of biologically relevant homophthalimide and 3-aminoisocoumarin nuclei via palladium-catalyzed carbonylation of 2-(2-iodoaryl)acetamides has been developed. The degree of N-substitution on the starting amide substrate dictates whether C?N or
Montmorillonite-KSF-catalyzed synthesis of 4-heteroarylidene-N-arylhomophthalimides by Knoevenagel condensation
Krishnakumar, Varadhan,Khan, Fazlur-Rahman Nawaz,Mandal, Badal Kumar,Jeong, Euh-Duck,Jin, Jong Sung
, p. 5509 - 5519 (2015/07/08)
A simple, efficient and rapid method for clay-catalyzed Knoevenagel condensation of heterocyclic aldehydes with active methylene compound under reflux condition is reported. This protocol offers high yield, shorter time and simple work procedure. The protocol does not require column chromatography for purification, and the process is environmentally benign.
Microwave promoted one-pot synthesis of some novel N-aryl isoquinoline derivatives
Havaldar, Freddy H.,Mule, Ganesh B.,Dabholkar, Bhushan V.
, p. 828 - 837 (2013/08/23)
Homophthalic anhydride 1 reacts with different aromatic amines to produce N-substituted homophthalimides 2 under microwave irradiation. A rapid microwave-assisted chemical synthesis of condensed 4-substituted furo[2,3-c]isoquinoline-1,5(2H,4H)-diones 3 an
Flower-shaped ZnO nanoparticles as an efficient, heterogeneous and reusable catalyst in the synthesis of N-arylhomophthalimides and benzannelated isoquinolinones
Krishnakumar, Varadhan,Kumar, Kesarla Mohan,Mandal, Badal Kumar,Khan, Fazlur-Rahman Nawaz
, p. 1881 - 1892 (2013/02/22)
A simple and green protocol, developed utilizing an efficient, heterogeneous and recyclable catalyst, i.e. zinc oxide nanoparticles (ZnO NPs)-mediated synthesis of N-arylhomophthalimides and benzannelated isoquinolinones, is reported. The structures of th
