• Title/Summary/Keyword: 2-Aminoindan

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Synthesis of 5,6-difluoro-2-aminoindan.HCI (5,6-디플루오르 -2-아미노인단.염산염의 합성)

  • 마은숙
    • YAKHAK HOEJI
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    • v.43 no.6
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    • pp.751-755
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    • 1999
  • 3,4-Difluoroamphetamine.HCI and 5,6-difluoro-2-aminoindan.HCI were synthesized as serotonergic agents. 3,4-Difluorobenzaldehyde was condensed with nitroethane and reduced with $LiAlH_4$ to obtain 3,4-difluoroamphetamine. And 5,6-difluoro-2-aminoidan.HCI was synthesizd through reactions of condensation with malonic acid, 10% Pd-C reduction, cyclization with polyphosphoric acid, oximation and catalytic hydrogenation.

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Synthesis of (S)-5-iodo-2-aminoindan.HCI ((S)-5-요오드 -2-아미노인단.염산염의 합성)

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

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Efficient Synthesis of 2-Aminoindan and cis-(${\pm}$)-4,4a,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one (2-Aminoindan 및 cis- ( ${\pm}$ ) -4,4a,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one의 효율적 합성)

  • Kim, Min-Woo;Ma, Eun-Sook
    • YAKHAK HOEJI
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    • v.50 no.6
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    • pp.403-408
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    • 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.

Synthesis of 6-amino-2-N-(n-propionylamino)selenazolo[4,5-f]indan (6-Amino-2-N-(n-propionylamino)selenazolo[4,5-f]indan의 합성)

  • Kim, Min-Kyeom;Ma, Eun-Sook
    • YAKHAK HOEJI
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    • v.52 no.1
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    • pp.20-26
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    • 2008
  • 2-Aminothiazole ring as a bioisoster of catechol in dopamine has provided with good oral availability and lipophilic property. Selenium was reported to have an improved antioxidant ability and to reduce the loss of dopamine. 2-Aminoindan, is a rigid form of dopamine, was evaluated as a dopamine agonist with low neurotoxocity. In order to develop a novel dopamine agonist, we tried to synthesize the selenazoloaminoindan derivative that is a hybrid structure of aminoindan and aminoselenazole instead of aminothiazole. 2-Indanone-2-oxime was reduced with $TiCl_4$ and $NaBH_4$ to form 2-aminoindan, which was reacted with propionyl chloride to give 2-N-n-propionylaminoindan (2). Compound 2 was reduced with $TiCl_4$ and $NaBH_4$ to afford 2-N-n-propylaminoindan (3) and it was nitrated and reduced to form 5-amino-2-N-n-propylaminoindan (5), which was reacted with KSeCN, $Br_2$, and glacial acetic acid to give 4,6-dibromo-5- amino-2-N-n-propylaminoindan (7) instead of selenazole ring formation. Otherwise, compound 2 was nitrated and hydrogenated to form 5-amino-2-N-n-propionylaminoindan (9), which was treated with KSeCN, $Br_2$, and glacial acetic acid to give 4,6-dibromo-5-amino-2-N-n-propionylaminoindan (10). Compound 9 was cyc1ized with KSeCN and glacial acetic acid in the absence of $Br_2$ to give 6-amino-2-N-(n-propionylamino)selenazolo[4,5-f]indan (11).

Ring enlargement reaction of 5,6-dimethoxyindan-2-one

  • Ma, Eun-Sook;Jung, Won-Young;Choi, Tae-Young
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.181.1-181.1
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    • 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)

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Synthesis of (${\pm}$)-cis-8-amino-l-2,3,4,4a,5,10b-hexahydrothiazolo[4,5-f]indeno [1,2-b][1,4]oxazine ((${\pm}$)-cis-8-Amino-2,3,4,4a,5,10b-hexahydrothiazolo[4,5-f]indeno [1,2-b][1,4]oxazine의 합성)

  • Ma, Eun-Sook
    • YAKHAK HOEJI
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    • v.52 no.6
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    • pp.488-493
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    • 2008
  • 2-Aminothiazole ring as a bioisoster of catechol in dopamine has provided with good oral availability and lipophilic property. 2-Aminoindan, is a rigid form of dopamine, was evaluated as a dopamine D3 agonist with low neurotoxicity. Dopamine D3 agonist was evaluated as selective for the treatment of Parkinson's disease. In order to develop a novel dopamine D3 agonist, we tried to synthesize the aminothiazoloindenoxazine derivative that is a hybrid structure of aminoindenoxazine and thiazole ring. cis-2-Amino-1-indanol (2) was synthesized from 1,2-indandione-2-oxime by catalytic hydrogenation and it was treated with chloroacetyl chloride and NaH in benzene solution to give (${\pm}$)-cis-4,4a,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one (6). Nitration of 6 by the mixed acid gave 8-nitro compound (7) and the carbonyl group of 7 was reduced with $LiAlH_4$ to afford compound (8). 8 was reduced to form (${\pm}$)-cis-8-amino-2,3,4,4a,5,9b-hexahydroindeno[1,2-b][1,4]oxazine (9) and finally it was cyclized with KSCN in glacial acetic acid to yield (${\pm}$)-cis-8-amino-2,3,4,4a,5,10b-hexahydrothiazolo[4,5-f]indeno[1,2-b][1,4]oxazine (10).