Modified Riemschneider Reaction of 3-Thiocyanatoquinolinediones

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F12%3A43867961" target="_blank" >RIV/70883521:28110/12:43867961 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1002/hlca.201200049" target="_blank" >http://dx.doi.org/10.1002/hlca.201200049</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/hlca.201200049" target="_blank" >10.1002/hlca.201200049</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Modified Riemschneider Reaction of 3-Thiocyanatoquinolinediones

Popis výsledku v původním jazyce

The Riemschneider reaction of 3-thiocyanatoquinoline-2,4(1H,3H)-diones with conc. H 2SO 4 was investigated. Using different reaction conditions, 13 types of reaction products were isolated. Compounds bearing a Me, Et, or Bu group at C(3) afforded mainly[1,3]thiazolo[5,4-c]quinoline-2,4- diones and 1,9b-dihydro-9b-hydroxythiazolo[5,4-c]quinoline-2,4-diones. In the case of the 3-Bu derivatives of the starting compounds, C-debutylation was also observed. If a Bn group is present at C(3), rapid C-debenzylation of the starting thiocyanates occurred, yielding [1,3]oxathiolo[4,5-c]quinoline-2,4- diones, and mixtures of mono-, di-, and trisulfides derived from 4-hydroxy-3-sulfanylquinoline-2-ones. The reaction mechanism of all of the transformations is discussed. All new compounds were characterized by IR, 1H- and 13C-NMR, and EI and ESI mass spectra, and in some cases, 15N-NMR spectra were also used to characterize new compounds.

Název v anglickém jazyce

Modified Riemschneider Reaction of 3-Thiocyanatoquinolinediones

Popis výsledku anglicky

The Riemschneider reaction of 3-thiocyanatoquinoline-2,4(1H,3H)-diones with conc. H 2SO 4 was investigated. Using different reaction conditions, 13 types of reaction products were isolated. Compounds bearing a Me, Et, or Bu group at C(3) afforded mainly[1,3]thiazolo[5,4-c]quinoline-2,4- diones and 1,9b-dihydro-9b-hydroxythiazolo[5,4-c]quinoline-2,4-diones. In the case of the 3-Bu derivatives of the starting compounds, C-debutylation was also observed. If a Bn group is present at C(3), rapid C-debenzylation of the starting thiocyanates occurred, yielding [1,3]oxathiolo[4,5-c]quinoline-2,4- diones, and mixtures of mono-, di-, and trisulfides derived from 4-hydroxy-3-sulfanylquinoline-2-ones. The reaction mechanism of all of the transformations is discussed. All new compounds were characterized by IR, 1H- and 13C-NMR, and EI and ESI mass spectra, and in some cases, 15N-NMR spectra were also used to characterize new compounds.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2012

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Helvetica Chimica Acta

ISSN

0018-019X

e-ISSN

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Svazek periodika

95

Číslo periodika v rámci svazku

8

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

21

Strana od-do

1352-1372

Kód UT WoS článku

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EID výsledku v databázi Scopus

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