4767-56-0Relevant articles and documents
Stereoselective synthesis of (Z)-3-ylidenephthalides via AlCl3-mediated cyclization with 2-acylbenzoic acids
Feng, Ziming,Jiang, Jianshuang,Li, Gangsheng,Wang, Xujie,Yang, Yanan,Zhang, Peicheng,Zhang, Xu
, (2020)
An efficient method for the synthesis of (Z)-3-ylidenephthalides is reported in moderate to high yield with AlCl3 as catalyst. Different substrates of the 2-acylbenzoic acids are well performed in the Z/E selectivity. This method is highlighted
A palladium iodide catalyzed regioselective carbonylative route to isocoumarin and thienopyranone carboxylic esters
Carfagna, Carla,Centore, Roberto,Cuocci, Corrado,Della Ca', Nicola,Gabriele, Bartolo,Mancuso, Raffaella,Novello, Mariangela,Olivieri, Diego,Ziccarelli, Ida
, p. 164 - 182 (2021/12/20)
The reactivity of 2-alkynylbenzoic acids under PdI2/KI-catalyzed oxidative alkoxycarbonylation conditions, with oxygen (from air) as external oxidant and an alcohol as external nucleophile, has been studied. It was found that substrates with triple bond substituted with a bulky alkyl group, such as tert-butyl, selectively underwent a 6-endo-dig cyclization - alkoxycarbonylation pathway with ethanol or isopropanol as nucleophile, to give high value added isocoumarin-4-carboxylic esters in good to high yields (67–87%). When applied to alkynylthiophencarboxylic acids bearing an internal triple bond, the reaction turned out to be completely regioselective toward the formation of the corresponding alkyl thienopyranonecarboxylates ensuing from 6-endo-dig cyclization-alkoxycarbonylation, regardless the nature of the substituent on the triple bond and the external alcohol (54–91% yields). To confirm the structure of the products deriving from different kinds of substrates, and therefore to corroborate the proposed mechanistic pathways, the crystalline structures of 11 new compounds have been resolved by XRD analysis.
Stereoselective synthesis method of (Z)-3-alkenyl phthalide derivative
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Paragraph 0021; 0083-0087, (2021/06/23)
The invention discloses a stereoselective synthesis method of a (Z)-3-alkenyl phthalide derivative, which comprises the specific steps of stereoselectively synthesizing the (Z)-3-alkenyl phthalide derivative from a 2-acyl benzoic acid compound under the catalytic action of aluminum trichloride, dissolving the 2-acyl benzoic acid compound shown in a formula (I) defined in the description as a raw material in an organic solvent, and stereoselectively preparing a compound as shown in a formula (II) defined in the description by taking Al as a catalyst. According to the synthesis method of the (Z)-3-alkenyl phthalide derivative, the used catalyst is cheap and easy to obtain, the reaction condition is mild, the product is easy to purify, the stereoselectivity is good, the yield is high, the synthesis method is suitable for industrial production, and a new method is provided for preparing the (Z)-3-alkenyl phthalide derivative.
Use of Imidazo[1,5-a]pyridin-3-ylidene as a Platform for Metal-Imidazole Cooperative Catalysis: Silver-Catalyzed Cyclization of Alkyne-Tethered Carboxylic Acids
Rawat, Vishal Kumar,Higashida, Kosuke,Sawamura, Masaya
supporting information, p. 1631 - 1637 (2021/02/03)
Silver complexes with 5-(4-(tert-butyl)-1H-imidazol-1-yl)-imidazo[1,5-a]pyridin-3-ylidene ligands were synthesized as metal-imidazole acid-base cooperative catalysts. Single crystal XRD analysis revealed that the silver atom was located in the vicinity of
Palladium/Copper-Catalyzed Denitrogenative Alkylidenation and ortho-Alkynylation Reaction of 1,2,3-Benzotriazin-4(3 H)-ones
Hari Balakrishnan, Madasamy,Mannathan, Subramaniyan
supporting information, p. 542 - 546 (2020/02/04)
An efficient palladium-catalyzed approach to access various functionalized (Z)-3-benzylidene-isoindoline-1-ones and (Z)-3-benzylidene(imino)isobenzofuranones via a denitrogenative tandem alkynylation/cyclization reaction of 1,2,3-benzotriazin-4(3H)-ones w
Iridium-Catalyzed Cycloisomerization of Alkynoic Acids: Synthesis of Unsaturated Lactones
Huang, Yi,Zhang, Xianghe,Dong, Xiu-Qin,Zhang, Xumu
, p. 782 - 788 (2020/01/08)
The iridium-catalyzed cycloisomerization of various alkynoic acids was successfully developed, and a series of five-, six-, and especially seven-membered unsaturated lactones were constructed with moderate yields and excellent regioselectivities (up to 68
Imidazo[2,1-a]isoindole scaffold as an uncharted structure active on Leishmania donovani
Arsène, Sobinson,Gómez-Pérez, Verónica,Escarcena, Ricardo,Abengózar, María ángeles,García-Hernández, Raquel,Nácher-Vázquez, Montserrat,San Feliciano, Arturo,Gamarro, Francisco,Rivas, Luis,Olmo, Esther del
, (2019/08/16)
The human protozoan parasites Leishmania donovani and L. infantum are the causative agents of visceral leishmaniasis, as such, responsible for approximately 30,000 deaths annually. The available chemotherapeutic treatments are reduced to a few drugs whose effectiveness is limited by rising drug resistance/therapeutic failure, and noxious side-effects. Therefore, new therapeutic hits are needed. Compounds displaying the imidazo[2,1-a]isoindole skeleton have shown antichagasic, anti-HIV, antimalarial and anorectic activities. Here, we report the leishmanicidal activity of thirty one imidazo[2,1-a]isoindol-5-ol derivatives on promastigotes and intracellular amastigotes of L. donovani. Eight out of thirty one assayed compounds showed EC50 values ranging between 1 and 2 μM with selectivity indexes from 29 to 69 on infected THP-1 cells. Six compounds were selected for further elucidation of their leishmanicidal mechanism. In this regard, compound 29, the imidazoisoindolol with the highest activity on intracellular amastigotes, induced an early decrease of intracellular ATP levels, as well as mitochondrial depolarization, together with a partial plasma membrane destructuration, as assessed by transmission electron microscopy. Consequently, the inhibition of the energy metabolism of Leishmania plays an important role in the leishmanicidal mechanism of this compound, even when other additional targets cannot be ruled out. In all, the results supported the inclusion of the imidazoisoindole scaffold for the development of new leishmanicidal drugs.
Ag2O nanoparticle-catalyzed substrate-controlled regioselectivities: direct access to 3-ylidenephthalides and isocoumarins
Chaudhary, Sandeep,Shyamlal, Bharti Rajesh K.,Yadav, Lalit,Tiwari, Mohit K.,Kumar, Krishan
, p. 23152 - 23162 (2018/07/10)
Herein, we disclose the first example of an efficient, silver oxide nanoparticle-catalyzed, direct regioselective synthesis of 3-ylidenephthalides 11-16 and isocoumarins 17-20via sonogashira type coupling followed by substrate-controlled 5-exo-dig or 6-endo-dig cyclization reaction, respectively. This one pot coupling involves reaction of substituted 2-halobenzoic acid with meta/para-substituted and ortho-substituted terminal alkynes, which proceeded in a regioselective manner resulting in the formation of 3-ylidenephthalides or isocoumarins, respectively, in excellent yields (up to 95%) with complete Z-selectivity. This protocol features relatively broad substrate scope, mild conditions, operational simplicity, and is favourable with aromatic/alicyclic terminal alkynes. The competition experiments and gram-scale synthesis further highlight the importance and versatility of the methodology. The proposed mechanistic pathways illustrate that the regioselectivity is substantially being controlled by the substituent(s) present on the acetylenic phenyl ring.
Divergent Syntheses of (Z)-3-Alkylideneisobenzofuran-1(3 H)-ones and 1 H-Isochromen-1-ones by Copper-Catalyzed Cycloisomerization of 2-Alkynylbenzoic Acids in Ionic Liquids
Mancuso, Raffaella,Pomelli, Christian S.,Chiappetta, Piera,Gioia, Katia F.,Maner, Asif,Marino, Nadia,Veltri, Lucia,Chiappe, Cinzia,Gabriele, Bartolo
, p. 6673 - 6680 (2018/06/01)
The cycloisomerization of readily available 2-alkynylbenzoic acids 1 in ionic liquids (ILs) as recyclable reaction media has been studied under the catalytic action of CuCl2. With substrates bearing an aryl group on the triple bond, a mixture o
A highly active diradical cobalt(iii) catalyst for the cycloisomerization of alkynoic acids
Leconte, Nicolas,Du Moulinet D'Hardemare, Amaury,Philouze, Christian,Thomas, Fabrice
supporting information, p. 8241 - 8244 (2018/07/29)
The first cobalt-catalysed cycloisomerisation of alkynoic acids is reported, thanks to the design of a well-defined diradical cobalt(iii) catalyst, in the absence of any additives. The high efficiency, regioselectivity and chemoselectivity are comparable to those of noble metal-based systems. The unique reactivity might be attributed to second coordination sphere effects.
