Hydantoins and Thiohydantoins Derived from 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F06%3A00004386" target="_blank" >RIV/00216275:25310/06:00004386 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11160/06:00006928
Result on the web
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DOI - Digital Object Identifier
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Alternative languages
Result language
angličtina
Original language name
Hydantoins and Thiohydantoins Derived from 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid
Original language description
The reaction of methyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate with isocyanates and isothiocyanates has been used to prepare N-substituted methyl (3S)-2-aminocarbonyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylates. These compounds were cyclised by action of CF3COOH or triethylamine to give the corresponding 2-substituted (10aS)-10,10a-dihydroimidazo[1,5-b]isoquinoline-1,3(2H,5H)-diones (hydantoines Tic-H) and 2-substituted (10aS)-3-thioxo-1,2,3,5,10,10a-hexahydroimidazo[1,5-b]isoquinolin-1-ones(thiohydantoines Tic-TH) respectively. All the substances were characterised by means of 1H and 13C NMR spectra, elemental analyses, and the non-racemic substances also by means of optical rotation. The optical purity of selected substances was determined chromatographically.
Czech name
Hydantoiny a thiohydantoiny odvozené od 1,2,3,4-tetrahydroisochinolin-3-karboxylové kyseliny
Czech description
Reakcí methyl (S)-1,2,3,4-tetrahydroisochinolin-3-carboxylátu s isokyanáty and isothiokyanáty byly připraveny N-substituované methyl (3S)-2-aminokarbonyl-1,2,3,4-tetrahydroisochinolin-3-karboxyláty. Tyto látky byly působením CF3COOH nebo triethylaminu cyklizovány na 2-substituované (10aS)-10,10a-dihydroimidazo[1,5-b]isochinolin-1,3(2H,5H)-diony (hydantoiny Tic-H) resp. 2-substituované (10aS)-3-thioxo-1,2,3,5,10,10a-hexahydroimidazo[1,5-b]isochinolin-1-ony (thiohydantoiny Tic-TH). Všechny látky byla charakterizovány 1H and 13C NMR spektry, elementárními analýzami, neracemické látky rovněž optickou rotací. Optická čistota vybraných látek byla stanovena chromatograficky.
Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
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Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)
Others
Publication year
2006
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Heterocycles
ISSN
0385-5414
e-ISSN
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Volume of the periodical
68
Issue of the periodical within the volume
12
Country of publishing house
JP - JAPAN
Number of pages
21
Pages from-to
2527-2547
UT code for WoS article
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EID of the result in the Scopus database
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