76464-99-8Relevant articles and documents
Metal-Catalyzed Cyclotrimerization Reactions of Cyanamides: Synthesis of 2-Aryl-α-carbolines
Edioma, Friendship B.,Lesch, Robert W.,Medas, Kyle M.,Mulcahy, Seann P.,Ndahayo, Vincent,Wrenn, Sean P.
, p. 3135 - 3139 (2020)
The synthesis of annulated 2-aryl-α-carboline heterocycles is described using transition metal catalysis. A linear strategy is described that uses Rh(I) catalysis to form the α-carboline scaffold by [2+2+2] cyclotrimerization. Alternatively, a tandem catalytic approach using a Pd(II) precatalyst afforded the same target molecules by mediating a Sonogashira reaction and a [2+2+2] cyclotrimerization in the same reaction flask. In each case, nine different 2-aryl-α-carbolines have been prepared in high to modest isolated yields.
Acid-Promoted Expeditious Syntheses of Aminated Dibenzosultams via Palladium/Norbornene Cooperatively Catalysed C?H Amination/Arylation
Zhao, Shen,Han, Shibo,Du, Guopeng,Zhang, Daopeng,Liu, Hui,Li, Xinjin,Dong, Yunhui,Sun, Feng-Gang
supporting information, p. 2078 - 2083 (2021/03/01)
Herein we reported a protocol to access aminated benzofused sultams through sequential ortho-amination, followed by ipso-arylation of aryl iodide bearing sulfonamide functional group via palladium/norbornene coorperative catalysis. This reaction has showcased a broad spectrum of substrate scope under mild conditions with moderate to good efficiency. (Figure presented.).
Catalytic and Enantioselective Control of the C–N Stereogenic Axis via the Pictet–Spengler Reaction
Kim, Ahreum,Kim, Aram,Park, Sunjung,Kim, Sangji,Jo, Hongil,Ok, Kang Min,Lee, Sang Kook,Song, Jayoung,Kwon, Yongseok
supporting information, p. 12279 - 12283 (2021/05/03)
An unprecedented example of a chiral phosphoric acid-catalyzed atroposelective Pictet–Spengler reaction of N-arylindoles is reported. Highly enantioenriched N-aryl-tetrahydro-β-carbolines with C?N bond axial chirality are obtained via dynamic kinetic reso
Modular counter-Fischer?indole synthesis through radical-enolate coupling
Chung, Hyunho,Kim, Jeongyun,Gonzalez-Montiel, Gisela A.,Cheong, Paul Ha-Yeon,Lee, Hong Geun
supporting information, p. 1096 - 1102 (2021/01/26)
A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.
Site-Selective Double and Tetracyclization Routes to Fused Polyheterocyclic Structures by Pd-Catalyzed Carbonylation Reactions
Bacchi, Alessia,Carfagna, Carla,Costa, Mirco,Della Ca', Nicola,Gabriele, Bartolo,Mancuso, Raffaella,Mazzeo, Paolo P.,Pancrazzi, Francesco,Sarti, Nicolò,Stirling, András
supporting information, p. 1569 - 1574 (2020/03/13)
In this contribution, we report novel palladium-catalyzed carbonylative cascade approaches to highly functionalized polyheterocyclic structures. The Pd-catalyzed carbonylative process involves the regioselective insertion of one to three CO molecules and the sequential ordered formation of up to eight new bonds (one C-O, two C-C, five C-N). The exclusive formation of six-membered heterocycles is elucidated by detailed modeling studies.
Studies towards the Total Synthesis of Drimentine C. Preparation of the AB and CDEF Ring Fragments
Pound, Sarah M.,Underwood, Steven J.,Douglas, Christopher J.
supporting information, p. 2448 - 2453 (2020/04/27)
The drimentine family is a class of hybrid isoprenoids derived from actinomycete bacteria. Members of this family display weak antitumor and antibacterial activity. Herein we report our efforts toward the total synthesis of drimentine C using three distinct approaches incorporating palladium-catalyzed cyanoamidation, reductive cross-coupling, and photoredox-catalyzed α-alkylation of an aldehyde as key steps. Our synthetic efforts use a convergent synthesis to assemble the terpenoid and alkaloid portions of drimentine C from readily available l-tryptophan, l-proline, and (+)-sclareolide.
A carboxylate-assisted amination/unactivated C(sp2)-H arylation reactionviaa palladium/norbornene cooperative catalysis
An, Yang,Zhang, Bo-Sheng,Zhang, Zhe,Liu, Ce,Gou, Xue-Ya,Ding, Ya-Nan,Liang, Yong-Min
supporting information, p. 5933 - 5936 (2020/06/04)
This report describes a carboxylate-assisted palladium-catalysed Catellani reaction, which is compatible withortho-amination and unactivated C(sp2)-H arylation. This method was used to synthesize a series of 1-amino substituted dihydrophenanthridines, phenanthridines and 6H-benzo[c]chromenes. Based on kinetic isotope experiments, the kinetic curve proves that pivalic acid accelerates the reaction rate of unactivated C(sp2)-H activation, and thus this rate can keep up with the five membered aryl-norbornene-palladacycle (ANP) intermediate.
Indazole 2-oxides compound and method for preparing indazole 2-oxides compound for providing a nitrogen heterocyclic compound used as a precursor for drugs
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Paragraph 0013; 0014, (2019/08/28)
Provided is a method for preparing an indazole 2-oxides compound, which comprises the step of: performing a cyclization reaction on 2-alkynyl aniline compound and tert-butylnitrite represented by formula (1) in the presence of bis(dibenzylideneacetone) palladium so as to produce an indazole 2-oxides compound, in which, in the formulae (1) and (2), R1 , R2 , R3 and R4 are each hydrogen, halogen or alkyl group; X1 represents an alkyl group, a first chemical structure, a second chemical structure or a third chemical structure where T1 , T2 , T3 , T4 and T5 are each hydrogen, halogen, alkoxy group, or alkyl group; X2 represents hydrogen, cycloalkyl group, alkyl group, alkenyl group, thienyl group, unsubstituted phenyl group, or substituted phenyl group, where the substituent is selected from the group consisting of an alkyl group, an alkoxy group, a halogen, a haloalkyl group, -CN, or -NO2.
Reactivity of Alkyne Insertion and Catalytic Activity of Five- and Six-Membered Cyclometalated Phosphine Complexes of Iridium
Li, Tongyu,Wang, Zhuo,Liu, Kai,Xing, Siyang,Zhu, Bolin
, p. 3195 - 3202 (2018/07/31)
Reactions of three aryl-substituted phosphines with [Cp*IrCl2]2 afforded the corresponding five-membered or six-membered cyclometalated iridium complexes (2 or 5,6) via an intramolecular C(sp2)–H bond activation. Insertion reactions of the five-membered cycloiridated complex 2 with PhC≡CPh and PhC≡CCOPh resulted in the corresponding five-membered and six-membered doubly cycloiridated complexes 7 and 8, the formation of which presumably went through the vinylidene rearrangement of alkynes followed by 1,1-insertion; while the reactions of the six-membered cyclometalated complexes 5, 6 with PhC≡CPh or PhC≡CCOPh gave the corresponding eight-membered cycloiridated complexes 9–12 by 1,2-insertion. The hydrosilylation of imines catalyzed by five- or six-membered P-containing cycloiridated complexes were studied, and the results proved that the six-membered cycloiridated complex 5 can be used as an efficient catalyst, which was applied for the hydrosilylation of various imines, especially aldimines. Molecular structures of complexes 9, 10 and 12 were determined by X-ray diffraction.
A catalyst-free and additive-free method for the synthesis of benzothiazolethiones from: O -iodoanilines, DMSO and potassium sulfide
Zhu, Xiaoming,Li, Wenguang,Luo, Xiai,Deng, Guobo,Liang, Yun,Liu, Jianbing
supporting information, p. 1970 - 1974 (2018/05/23)
Under catalyst-free and additive-free conditions, a novel, convenient, eco-friendly method for the synthesis of benzothiazolethiones has been developed. The three-component reaction of o-iodoanilines and K2S with DMSO proceeded smoothly and the corresponding benzothiazolethiones were obtained with good isolated yields. Meanwhile, this method could be used for the synthesis of thioureas from primary diamines. Furthermore, mechanism research showed that DMSO not only functioned as a carbon source, but also as a mild oxidant in this reaction.
