• YAKHAK HOEJI
• /
• v.50 no.6
• /
• pp.403-408
• /
• 2006

1-Amino-5,6-dimethoxyindan hydrochloride was synthesized from 3- (3,4-dirnethoxyphenyl)propionic acid by intramolecular Friedel-Crafts acylation, oximation with hydroxylamine, and reduction with an overall yield of 74%. 2-Amino-5,6-dimethoxyindan hydrochloride was synthesized from 3-(3,4-dirnethoxyphenyl)propionic acid by intramolecular Friedel-Crafts acylation, oximation with isoamylnitrite, reduction in NaOH and reaction with HCI to form 5,6-dimethoxy-2-indanone, which was reacted with hydroxylamine and reduced with an overall yield of 42%. 5,6-Dimethoxyindan-1,2-dione-2-oxime, which was catalytically hydrogenated to afford cis-, and trans-1-amino-5,6-dimethoxyindan-1-ol as 3 : 1 ratio. This mixture was treated with Li and reacted with chloroacetyl chloride. Cis isomer was acylated and cyclized to synthesize rir -( ${\pm}$ )-7,8-dimethoxy-4,4a,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one, but trans isomer was just acylated to form amide.

• YAKHAK HOEJI
• /
• v.38 no.5
• /
• pp.504-510
• /
• 1994

A facile synthesis of 2-aryl-5-benzoxazolepropionic acid derivatives(1 0a-d), which are potent antiinflammatory agent, is reported. Methyl ${\alpha}$-(p-hydroxyphenyl)propionate(5) was prepared from Friedel-Crafts reaction of isopropoxy benzene with methyl ${\alpha}$-chloro-${\alpha}$-(methylthio) acetate(1), followed by desulfurization, methylation and clevage of ether bond. Compounds(10a-d) were made from(5) by a sequence of nitration, reduction, formation of benzoxazole ring, and hydrolysis in good yields, respectively.

• YAKHAK HOEJI
• /
• v.43 no.1
• /
• pp.11-15
• /
• 1999

A brief route for regiospecific synthesis of novel 10-Oxodaunomycinone Derivatives (10a, b) is described. Dimethoxy-l-tetralone 4 was converted to acetyl tetralone (5a, b) which was oxidized with oxygen to obtain cis-diol compound (8a, b). The construction of (10a, b) was completed by the condensation of phthaloyl dichloride 9 with cis-diol (8a, b)

• YAKHAK HOEJI
• /
• v.32 no.5
• /
• pp.340-342
• /
• 1988

New synthetic method for ibuprofen, which is a potent antiinflammatory agent, was described. Ethyl ${\alpha}-methylthio-p-isobutylphenylacetate$ was obtained from Friedel-Crafts reaction of isobutylbenzene with ethyl ${\alpha}-chloro-{\alpha}-(methylthio)acetate$ in the presence of $SnCl_4$. Ibuprofen was prepared in good yield by treatment of ethyl ${\alpha}-methylthio-p-isobutylphenylacetate$ with NaH and MeI, followed by desulfurization with zinc dust-acetic acid and hydrolysis of the resultant ethyl 2-methylthio-2-(4-isobutylphenyl)propionate.

• Bulletin of the Korean Chemical Society
• /
• v.14 no.1
• /
• pp.79-81
• /
• 1993

Synthetic routes are described for the introduction of hydroxyalkyl groups to the upper rim of calix[4]arene. Treatment of p-bromocalix[4]arene methyl ether 3 with n-BuLi followed by para-formaldehyde produced p-hydroxymethylcalix[4]arene methyl ether 4 in 60% yield. p-Acetylcalix[4]arene methyl ether 7, obtained by Friedel-Crafts acetylation of calix[4]arene methyl ether 6, was reduced with NaBH4 to produce p-(1-hydroxy ethyl)calix[4]arene methyl ether 8 in 67% yield.

• Bulletin of the Korean Chemical Society
• /
• v.21 no.8
• /
• pp.774-778
• /
• 2000

A convenient total synthesis of a new 7-deoxyidarubicinone ivative21,the aglycon of the anticancer anti-biotic idarubicin analogue,is described.Keyfeatures of the synthesis are the Friedel-Crafts acylation and the functionalization of an A-ring si de chain. A synthon 14 for the A and B rings was prepared from intermediate 6 in five steps.

• Proceedings of the PSK Conference
• /
• 2003.10b
• /
• pp.181.1-181.1
• /
• 2003

2-Aminoindan derivatives has been shown the serotonergic activities. In order to find new serotonergic agent, we trid to enlarge the indan ring. 3, 4-Dimethoxybenzaldehyde, used as starting material was condensed with malonic acid, piperidine to form 3, 4-dimethoxycinnamic acid. It was catalytically hydrogenated and sudsequently cyclized by Friedel-Crafts acylation reaction to yield 5, 6-dimethoxyindanone. This compound was reacted with pyrrolidine and then acrylamide to be synthesized the 3-membered ring. (omitted)

• Bulletin of the Korean Chemical Society
• /
• v.34 no.9
• /
• pp.2604-2608
• /
• 2013

An efficient synthesis of 2,2'-dipyrryl ketones has been carried out from pyrrole-2-carboxylic acids using trifluoroacetic anhydride (TFAA). Simultaneous generation of both mixed anhydride and 2-unsubstituted pyrrole, via facile decarboxylation with in-situ generated TFA, made their cross reaction (intermolecular Friedel-Crafts acylation) possible and efficient.

• YAKHAK HOEJI
• /
• v.45 no.6
• /
• pp.582-587
• /
• 2001

(S)-5-iodo-2-aminoindan.HCI (7) was synthesized for developing a serotonergic agent. (S)- Phenylalanine was protected with trifuoroacetyl group and compound 2 was prepared by direct iodination in acetic acid and in the presence of I$_2$, KIO$_4$, and sulfuric acid. Compound 3 was cyclized by Friedel-Crafts reaction and reduced with NaBH$_4$ to form 5-iodo-2-(N-trifluoroacetyl)aminoindan-1-ol (4) . This compound was reduced to indan derivative 5 using the triethylsilane and BF$_3$ . Et$_2$O. It was basified with $K_2$CO$_3$ solution and treated with saturated HCl in ethyl ether to isolate compound 7.

• Korean Membrane Journal
• /
• v.4 no.1
• /
• pp.20-24
• /
• 2002

The surface of polysulfone membranes has been modified using the fluorine chemicals, ITFE (2-iodo-1,1,1-trifluoro-ethane F.W.=209.94) and PFPI (1H,1H-pentafluoro-n-propyl iodide F.W.=259.95), and PFI (1H,1H,2H,2H-perfluorohexyl iodide, F.W.=373.99) based on Friedel-Crafts reaction mechanism with varying reaction temperatures, reaction time, and catalysis types. The resulting membranes were characterized through mainly the contact angle measurement and pure water permeability. The smaller reactant shows the larger contact angles. FeBr$_3$ catalyst is more effective than AlCl$_3$. Typically, the PS film treated with ITFE at $25^{\circ}C$ under FeBr$_3$ catalyst showed the contact angle 78.5$^{\circ}C$ which indicated 10% over the value of unreacted PS films. More than 50% of pure water flux 8.0 g/$m^2$hr, reduced at reaction time 10 min relative to the original flux, 3.49 g/$m^2$hr.