• Bulletin of the Korean Chemical Society
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• 제27권12호
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• pp.2019-2022
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• 2006

(1S,2R)-cis-1-Amino-2-indanol has been synthesized. A unique feature of the synthesis involves securing the functionalities and the configurations of the two stereocenters on an acyclic precursor before cyclizing it into the final ring-skeleton. The strategy allows both the stereocenters to be controlled in an absolute manner.

• Bulletin of the Korean Chemical Society
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• 제22권11호
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• pp.1261-1263
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• 2001

• Bulletin of the Korean Chemical Society
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• 제22권4호
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• pp.401-404
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• 2001

A new chiral stationary phase (CSP) based on (1R,2S)-2-amino-1-indanol, which is expected to be conformationally rigid because of its cyclic nature, was prepared. The new CSP was applied in resolving various $N-acyl-\alpha-arylalkylamines$. The chromatographic resolution results on the new CSP were compared with those on the other CSP based on (1S,2R)-norephedrine, which is believed to be conformationally flexible. Comparison of the chromatographic resolution results on the two CSPs demonstrated that conformationally flexible analytes are resolved better on the conformationally rigid CSP while conformationally rigid analytes are resolved better on the conformationally flexible CSP. From these results it was concluded that conformational rigidity or flexibility of CSPs is the important factor for the chiral recognition.

• 약학회지
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• 제44권6호
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• pp.505-510
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• 2000

The synthesis of pentahydroindanoisoquinoline (4) compound has been achieved via the cyclization of 2-(N-benzylamino)-5,6-difluoro-1-indanol (10a, 10b), which was prepared by condensation and reduction of 2-amino-1-indanol and benzaldehyde in ethanol. The stereochemistry of $H_{6a}$ and $H_{11b}$ of 9,10-difluoro-5,6,6a,7,11b-pentahydroindano[2,1-c]isoquinoline (4) was the trans B/C ring fusion.

• 약학회지
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• 제52권6호
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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).

• Bulletin of the Korean Chemical Society
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• 제3권3호
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• pp.119-122
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• 1982

Rigid ${\alpha}$-oximino ketones containing two functional groups such as 2-oximino-1-acenaphthenone and 2-oximino-1-indanone were synthesized and the simultaneous reduction of the two functional groups of ${\alpha}$-oximino ketones by $LiAlH_4$ gave the corresponding amino alcohols, 2-amino-1-acenaphthenol and 2-amino-1-indanol. The yields of the reduction products of the ${\alpha}$ -oximino ketones remarkably increased, as the increase of molar ratio of hydride used to the reactant. The use of 24 moles of $LiAlH_4$ was found to afford the best result in the reduction of the rigid ${\alpha}$-oximino ketones to the corresponding amino alcohols. The yields was not affected by the variation of solvents such as ether, THF and diglyme.