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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

  • DOI - Digital Object Identifier

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

Result continuities

  • Project

  • 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

  • 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

  • EID of the result in the Scopus database