852292-27-4Relevant academic research and scientific papers
Palladium-Catalyzed Allenamide Carbopalladation/Allylation with Active Methine Compounds
Zhu, Xiaoyi,Li, Ruibo,Yao, Hequan,Lin, Aijun
supporting information, p. 4630 - 4634 (2021/06/28)
A palladium-catalyzed allenamide carbopalladation/allylation with active methine compounds has been developed. Various indoles and isoquinolinones bearing a quaternary carbon center were achieved with good efficiency, a broad substrate scope and good functional group tolerance. This reaction underwent cascade oxidative addition, carbopalladation, and allylic alkylation, and two new C-C bonds were formed in one pot.
Gold and Br?nsted Acid Catalyzed Spirocyclization of 2- And 3-Indolyl-Tethered 1,4-Enyne Acetates to Spiro[4, n]alkyl[ b]indoles
Baratay, Corentin Antoine,Chen, Xiaoyu,Hong Chan, Philip Wai,Mark, Maddison Elizabeth,Xu, Xinfang
supporting information, (2020/04/02)
A synthetic method to prepare spiro[4,n]alkyl[b]indoles (n = 4-6) efficiently that relies on the gold(I) and Br?nsted acid mediated spirocyclization of 2- and 3-indolyl-tethered 1,4-enyne acetates at room temperature and open to air is described.
Nickel-Catalyzed trans-Carboamination across Internal Alkynes to Access Multifunctionalized Indoles
Tambe, Shrikant D.,Iqbal, Naeem,Cho, Eun Jin
supporting information, p. 8550 - 8554 (2020/11/12)
A Ni-catalyzed reaction was developed for the synthesis of multifunctionalized indoles. The reaction proceeded through oxidative cyclization of the Ni(0)/P^N complex with an enyne system, 2-alkynyl anilinoacrylate, to provide a nickelacycle intermediate. The trans-carboamination around the internal alkyne was achieved by syn/anti-rotation of the Ni-carbenoid intermediate formed by C-N bond cleavage of the nickelacycle, and 3-alkenylated indoles were formed by C-N bond-forming reductive elimination. Notably, the synthesized indoles could be successfully transformed to functionalized carbazoles.
Organocatalytic Asymmetric Annulation of ortho-Alkynylanilines: Synthesis of Axially Chiral Naphthyl-C2-indoles
Peng, Lei,Li, Kai,Xie, Chuandong,Li, Shan,Xu, Da,Qin, Wenling,Yan, Hailong
supporting information, p. 17199 - 17204 (2019/11/11)
A chiral Br?nsted base catalyzed asymmetric annulation of ortho-alkynylanilines has been developed to access axially chiral naphthyl-C2-indoles via vinylidene ortho-quinone methide (VQM) intermediates. This strategy provides a unique organocatalytic atrop
11a-N-tosyl-5-carbapterocarpans: Synthesis, antineoplastic evaluation and in silico prediction of ADMETox properties
Mendes, Joseane A.,Salustiano, Eduardo J.,Pires, Carulini de S.,Oliveira, Thaís,Barcellos, Julio C.F.,Cifuentes, Jhonny M.C.,Costa, Paulo R.R.,Rennó, Magdalena N.,Buarque, Camilla D.
, p. 585 - 590 (2018/07/29)
11a-N-tosyl-5-carbapterocarpans (5a–c and 6a–c), 9-N-tosyl-4,4a,9,9a-tetrahydro-3H-carbazole (7), 11a-N-tosyl-5-carbapterocarpen (8) analogues of LQB-223 (4a), were synthesized through palladium catalyzed azaarylation of substituted dihydronaphtalenes (14a–c) and cyclohexadiene (15), respectively, with N-tosyl-o-iodoaniline (11). In order to understand the role of the N-tosyl moiety for the pharmacological activity, the azacarbapterocarpen (9) was also synthesized by Fischer indol reaction. The structural requirements at the A and D-rings for the antineoplastic activity toward human leukemias and breast cancer cells were evaluated as well. Substitutions on the A-ring of 4a and analogues alter the effect on different breast cancer subtypes. On the other hand, A-ring is not essential for antileukemic activity since compound 7, which does not contain the A-ring, showed efficacy with high selectivity indices for drug-resistant leukemias. On the other hand, substitutions on the D-ring of 4a for fluorine or iodine did not improve the antileukemic activity. In silico studies concerning Lipinskís rule of five, ADMET properties and drug scores of those compounds were performed, indicating good physicochemical properties for all compounds, in special for compound 7.
Synthesis and optical properties of 2-functionally substituted 4,5-dihydrothieno[3,2-c]quinolines
Bogza, Yulia P.,Rastrepin, Alexey A.,Nider, Victoria V.,Zheleznova, Tatyana Yu,Stasyuk, Anton J.,Kurowska, Aleksandra,Laba, Katarzyna,Ulyankin, Evgeny B.,Domagala, Wojciech,Fisyuk, Alexander S.
, p. 419 - 428 (2018/07/13)
N-Protected 4-(anilinomethyl)thiophene-2-carbaldehydes were prepared by the reaction of easily available 4-chloromethylthiophene-2-carbaldehyde with N-(2-halogenophenyl) substituted acetamides, 4-methylbenzenesulfonamides and carbamates in the presence of K2CO3 or Cs2CO3. The compounds obtained were converted to 4,5-dihydrothieno [3,2-c]quinoline-2-carbaldehydes by palladium catalyzed intramolecular cyclization in homogenous or heterogenous (Pd/C) conditions with good yields and subsequently used for preparing of 2-functionally substituted thieno [3,2-c]quinoline derivatives (nitriles, carboxamides, carboxylic acids, esters). The optical properties of 2-functionally substituted thieno[3,2-c]quinolines and 4H-thieno[3,2-c]chromenes have been studied. Moderate to high fluorescence quantum yields are observed for these compounds ranging from 0.15 to 0.87. Structure - optical properties relationships have been established for the compounds synthesized, and their prospective application as invisible ink dyes was practically demonstrated.
Parallel strategies for the synthesis of annulated pyrido[3,4-b]indoles via Rh(I)- and Pd(0)-catalyzed cyclotrimerization
Saliba, Bianca M.,Khanal, Satyam,O'Donnell, Michael A.,Queenan, Kathryn E.,Song, Junho,Gentile, Matthew R.,Mulcahy, Seann P.
, p. 4311 - 4314 (2018/11/03)
Two different pathways for the synthesis of annulated pyrido[3,4-b]indoles are reported using metal-catalyzed cyclotrimerization reactions. A stepwise process using Rh(I)-catalysis in the final step of the synthesis and a multicomponent, tandem catalytic
Dehydrogenation of N-Heterocycles by Superoxide Ion Generated through Single-Electron Transfer
Huang, Yuan-Qiong,Song, Hong-Jian,Liu, Yu-Xiu,Wang, Qing-Min
supporting information, p. 2065 - 2069 (2018/01/27)
Nitrogen-containing heteroarene motifs are found in numerous pharmaceuticals, natural products, and synthetic materials. Although several elegant methods for synthesis of these compounds through dehydrogenation of the corresponding saturated heterocycles have been reported, some of the methods are hampered by long reaction times, harsh conditions, and the need for catalysts that are not readily available. This work reports a novel method for dehydrogenation of N-heterocycles. Specifically, O2.? generated in situ acts as the oxidant for N-heterocycle substrates that are susceptible to oxidation through a hydrogen atom transfer mechanism. This method provides a general, green route to N-heteroarenes.
Pd-catalyzed cascade reactions between: O -iodo- N -alkenylanilines and tosylhydrazones: Novel approaches to the synthesis of polysubstituted indoles and 1,4-dihydroquinolines
Paraja, Miguel,Valdés, Carlos
supporting information, p. 6312 - 6315 (2016/05/19)
Two different Pd-catalyzed cascade reactions between o-iodo-N-alkenylanilines and tosylhydrazones are described. The outcome of the cascade processes is determined by the substitution on the N-alkenyl fragment. The reactions with N-tosyl-N-ethylene-o-iodoanilines lead to indoles through a sequence that involves the sequential migratory insertions of a carbene ligand and a C-C double bond, featuring a 5-exo-trig cyclization. The reactions with N-alkyl-N-alkenyl-o-iodoanilines provide 1,4-dihydroquinolines through a cascade reaction that includes a formal 6-endo-trig cyclization. In both cases the benzofused heterocycles are built through the formation of two C-C bonds on the hydrazonic carbon atom.
Creation of molecular complexities via a new Cu-catalyzed cascade reaction: A direct access to novel 2,2′-spirobiindole derivatives
Prasad, Bagineni,Adepu, Raju,Sharma, Atul Kumar,Pal, Manojit
supporting information, p. 1259 - 1262 (2015/02/05)
A Cu-mediated unprecedented cascade reaction in the presence of air afforded a conceptually new synthesis of 2,2′-spirobiindole derivatives. This reaction proceeds via the rearrangement of several bonds in a cyclopenta[b]indole framework including a facial selective intramolecular ring closure. The potential of this method is highlighted in the straightforward and single step synthesis of a paullone like compound. This journal is
