1127-59-9Relevant articles and documents
Double Carbonylation Using Glyoxal (HCOCOH): A Practical Copper-Promoted Synthesis of Isatins from Primary and Secondary Anilines
Kuan, Suzie Hui Chin,Sun, Wei,Wang, Lu,Xia, Chungu,Tay, Meng Guan,Liu, Chao
, p. 3484 - 3489 (2017)
A novel double carbonylation process has been demonstrated with easily available HCOCOH (glyoxal) as the double carbonylation reagent. Simple CuCl2?2H2O (copper(II) chloride dihydrate) was used as the oxidant for this transformation. Under optimized reaction conditions, various primary and secondary anilines were double-carbonylated to afford their corresponding isatins (26 examples, up to 80% yields). (Figure presented.).
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Newman,M.S.,Kannan,R.
, p. 3356 - 3359 (1976)
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Combretastatin A-4 analogues with benzoxazolone scaffold: Synthesis, structure and biological activity
Gerova, Mariana S.,Stateva, Silviya R.,Radonova, Elena M.,Kalenderska, Rositsa B.,Rusew, Rusi I.,Nikolova, Rositsa P.,Chanev, Christo D.,Shivachev, Boris L.,Apostolova, Margarita D.,Petrov, Ognyan I.
, p. 121 - 133 (2016)
In order to design and synthesize a new class of heterocyclic analogues of natural combretastatin A-4 and its synthetic derivative AVE8062, the benzoxazolone ring was selected as a scaffold for a bioisosteric replacement of the ring B of both molecules. A library of 28 cis- and trans-styrylbenzoxazolones was obtained by a modified Wittig reaction under Boden's conditions. Structures of the newly synthesized compounds bearing the 3,4,5-trimethoxy-, 3,4-dimethoxy-, 3,5-dimethoxy-, and 4-methoxystyryl fragment at position 4, 5, 6 or 7 of benzoxazolone core were determined on the basis of spectral and X ray data. The in vitro cytotoxicity of styrylbenzoxazolones against different cell lines was examined. Stilbene derivative 16Z, (Z)-3-methyl-6-(3,4,5-trimethoxystyryl)-2(3H)-benzoxazolone, showed highest antiproliferative potential of the series, with IC50 of 0.25 μM against combretastatin resistant cell line HT-29, 0.19 μM against HepG2, 0.28 μM against EA.hy926 and 0.73 μM against K562 cells. Furthermore, the results of flow cytometric analysis confirmed that 16Z induced cell cycle arrest in G2/M phase in the cell lines like combretastatin A-4. This arrest is followed by an abnormal exit of cells from mitosis without cytokinesis into a pseudo G1-like multinucleate state leading to late apoptosis and cell death. Accordingly, synthetic analogue 16Z was identified as the most promising potential anticancer agent in present study, and was selected as lead compound for further detailed investigations.
Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipole and Abnormal [3 + 2]-Cycloaddition with Maleimide in the Presence of 1,4-Diazabicyclo[2.2.2]octane
Wang, Xiao,Yang, Peng,Zhang, Yong,Tang, Chao-Zhe,Tian, Fang,Peng, Lin,Wang, Li-Xin
, p. 646 - 649 (2017)
A new isatin N,N′-cyclic azomethine imine synthon was devised, and an unexpected abnormal [3 + 2]-cycloaddition with maleimide catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) has been disclosed. A variety of tricyclic spiropyrrolidine oxindoles bearing a dinitrogen heterocycle and succinimide scaffold were obtained in excellent yields (up to 96%) and diastereoselectivities (up to 97:3) under mild conditions.
Study on synthesis of some substituted N-propargyl isatins by propargylation reaction of corresponding isatins using potassium carbonate as base under ultrasound- and microwave-assisted conditions
Tri, Nguyen Minh,Thanh, Nguyen Dinh,Ha, Luong Ngoc,Anh, Dang Thi Tuyet,Toan, Vu Ngoc,Giang, Nguyen Thi Kim
, p. 4793 - 4801 (2021/05/31)
Substituted N-propargyl isatins were synthesized by SN2 reaction of corresponding substituted isatins with propargyl bromide in the presence of anhydrous K2CO3 as base. We reported about study on systematically synthesis of these compounds using heating procedures under different reaction conditions, including microwave-assisted heating conditions at power of 100?W (Procedure A), conventional heating conditions in water bath at 50?°C in acetonitrile (Procedure B), and conventional heating conditions in water bath at 50?°C in DMF (procedure C). The best procedure A was deduced based on the investigations on the reaction conditions. Almost all substituted N-propargyl isatins were new, except compounds with R of H, 5-Me, 5-Cl and 5-Br substituents. The structures of the obtained compounds were confirmed by the modern spectroscopic methods.
Single step regioselective cyclization and chlorination of hydroxyamino-N-(2-methylphenyl)acetamide to 5-chloro-7-methylindoline-2,3-dione
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Page/Page column 5; 6, (2021/04/21)
A one-pot process for the manufacture of 5-chloro-7-methylindoline-2,3-dione starting from 2-hydroxyimino-N-(2-methylphenyl)acetamide via tandem cyclization in sulfuric acid and acetic acid, followed by in-situ chlorination with sulfur dioxide and chlorine gas in high regioselectivity and yield.
Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides
Schilling, Waldemar,Zhang, Yu,Riemer, Daniel,Das, Shoubhik
supporting information, p. 390 - 395 (2019/12/15)
Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied to dearomatise pyrrole derivatives to generate cyclic imides in a single step. Later this methodology was applied for the synthesis of four pharmaceuticals and a pesticide called dianthalexin B. Detailed mechanistic studies revealed the actual role of oxygen and photocatalyst.
