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Hydantoins and Thiohydantoins Derived from 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid
Authors: Jansa Petr | Wsól Vladimír | Bertolasi Valerio | Macháček Vladimír
Year: 2006
Type of publication: článek v odborném periodiku
Name of source: Heterocycles
Publisher name: The Japan Institute of Heterocyclic Chemistry
Place: Tokyo
Page from-to: 2527-2547
Titles:
Language Name Abstract Keywords
cze Hydantoiny a thiohydantoiny odvozené od 1,2,3,4-tetrahydroisochinolin-3-karboxylové kyseliny 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.
eng Hydantoins and Thiohydantoins Derived from 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid 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. Tic Acid, Hydantoin, Thiohydantoin, Atropoisomer, NMR Spectrum, X-Ray, Chiral HPLC

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