Reactions of lycoctonine alkaloids with acetic anhydride and p-toluenesulfonic acid

1991 ◽  
Vol 27 (4) ◽  
pp. 475-477
Author(s):  
A. S. Narzullaev ◽  
M. C. Yunusov
1982 ◽  
Vol 55 (5) ◽  
pp. 1538-1542 ◽  
Author(s):  
Ichiro Shimao ◽  
Ken Fujimori ◽  
Shigeru Oae

1976 ◽  
Vol 54 (4) ◽  
pp. 543-547 ◽  
Author(s):  
Alex Rosenthal ◽  
B. L. Cliff

Treatment of 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose (1) with sodium cyanide in anhydrous ethanol followed by addition of an equimolar amount of methyl nitro-acetate gave 3-C-cyano-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (2) in 57% yield. When methyl nitroacetate was first added to sodium cyanide in alcohol followed by the addition of ketose 1 then the allo-cyanohydrin epimer 4 was produced in 85% yield. 3-C-(Carbomethoxy-R,S-nitromethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (6) was produced in low yield in the latter reaction and was isolated and characterized as its 3-O-acetate derivative 7. Selective acetolysis of the 5,6-O-isopropylidene group of the branched-chain sugars was achieved using acetic anhydride and p-toluenesulfonic acid monohydrate. The proof of structure of the cyano-hydrins is described.


2021 ◽  
Author(s):  
Guofang Gao ◽  
Qian Zhao ◽  
Cheng Yang ◽  
Tingshun Jiang

Four imidazole ionic liquids acidified with p-toluenesulfonic acid were loaded on Bi-SBA-16 mesoporous materials to obtain four composite catalysts with strong acid properties. They were applied to acylation reaction of anisole and acetic anhydride.


2021 ◽  
Vol 9 (3) ◽  
Author(s):  
Renáta Gašparová ◽  
Katarína Kotlebová ◽  
Margita Lácová

Reactions of 4-hydroxycoumarin 1 with heterocyclic aldehydes 2-4 led to bis-4-hydroxycoumarin derivatives 5-7 under microwave irradiation as well as under the classical heating. The subsequent reactions of products 5-7 are described. 4,4’-Epoxydicoumarins 8, 9 were prepared by the reaction of 5-7 in acetic acid / p-toluenesulfonic acid medium. Compound 10 was prepared by the reaction of 5 in acetic anhydride in the presence sodium acetate. Dioxocine-1,15-dione 11 was prepared by the reaction of 6 with dichloromethane in sodium hydroxide-toluene.


2012 ◽  
Vol 152-154 ◽  
pp. 306-311
Author(s):  
Yuan Jun Song ◽  
Yan Wei Li ◽  
Bao Qing Pan ◽  
Hao Nan Song

2-acetoxy-6-naphthoic acid (ANA) was synthesized in the presence of 2-hydroxy -6-naphthoic acid (HNA) and acetic anhydride (CH3CO)2O with toluenesulfonic acid (PTSA) as catalyst. The effects of reactant ratio, temperature, time were investigated in the acetylation process. 1H-NMR、13C-NMR、FT-IR、HPLC measurements indicate the optimal acetylation reaction condition when the ratio of HNA: (CH3CO)2O : PTSA are 1: 2.3:0.025 under the temperature at 90~95°C for 40min.


1969 ◽  
Vol 61 (1_Suppl) ◽  
pp. S12 ◽  
Author(s):  
V. H. T. James ◽  
A. E. Rippon ◽  
M. L. Arnold

2020 ◽  
Vol 17 ◽  
Author(s):  
W. Abd El-Fattah

: In this work, 1,2,4-triazine derivatives were synthesized and evaluated for anticancer activities. Series of 1,2,4-triazine derivatives (4a, b) were prepared via the reaction of N-benzoyl glycine (1) with aromatic aldehydes in presence of fused sodium acetate and acetic anhydride to give 1,3-oxazolinone derivatives (2a, b), followed by condensation with 1-(ethoxycarbonyl) hydrazine (3) in glacial acetic acid. Compounds (4a, b) then reacted with acetic anhydride, ethyl chloroacetate and 2,4-dinitrophenyl hydrazine yielded the corresponding to N-acetyl derivatives (5a, b), N-(ethoxycarbonyl) methyl derivative (6) and 1,2-disubstituted hydrazine (7), respectively. The structures of the 1,2,4-triazine derivatives were confirmed by IR, 1H, 13C NMR, MS and elemental analyses. Anticancer activity of some 1,2,4-triazine derivatives (4-7) have been investigated. The results revealed that compounds 4a (IC50= 2.7μM), 5a (IC50= 1.5μM), and 5b (IC50= 3.9μM) show promising inhibitory growth efficacy compared to a standard antitumor drug (IC50= 4.6μM). These three compounds can be considered as potential agents against human hepatocellular carcinoma cell lines (HepG-2).


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