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Statements

Subject Item
n2:RIV%2F00216275%3A25310%2F12%3A39894706%21RIV13-MSM-25310___
rdf:type
skos:Concept n12:Vysledek
dcterms:description
Three series of S-(1(3H)-isobenzofuranone-3-yl)isothiuronium bromides differing in substitution at the isothiuronium moiety (none, one or two methyl groups) and at the benzene ring were prepared and characterized. These salts were then treated with various bases (acetate, triethylamine, Na2CO3) to give either 1-hydroxy-3-oxo-1,3-dihydro-2H-isoindol-2-carbothioamides or the product of S to N isobenzofuranone-3-yl migration, i.e., 1,3-dimethyl-1-(3-oxo-1,3-dihydro-2-benzofuran-1-yl)thioureas. If ammonia was used in reaction with N,N'-dimethyl isothiuronium salts then 3-hydroxy-2,3-dihydro-1H-isoindol-1-ones were formed together with 1,3-dimethyl-1-(3-oxo-1,3-dihydro-2-benzofuran-1-yl)thioureas in parallel reaction with the yields increasing with ammonia concentration. The formation of isoindolones takes place in two steps with an aldehyde intermediate, which can be trapped with N,N-dimethylhydrazine. Three series of S-(1(3H)-isobenzofuranone-3-yl)isothiuronium bromides differing in substitution at the isothiuronium moiety (none, one or two methyl groups) and at the benzene ring were prepared and characterized. These salts were then treated with various bases (acetate, triethylamine, Na2CO3) to give either 1-hydroxy-3-oxo-1,3-dihydro-2H-isoindol-2-carbothioamides or the product of S to N isobenzofuranone-3-yl migration, i.e., 1,3-dimethyl-1-(3-oxo-1,3-dihydro-2-benzofuran-1-yl)thioureas. If ammonia was used in reaction with N,N'-dimethyl isothiuronium salts then 3-hydroxy-2,3-dihydro-1H-isoindol-1-ones were formed together with 1,3-dimethyl-1-(3-oxo-1,3-dihydro-2-benzofuran-1-yl)thioureas in parallel reaction with the yields increasing with ammonia concentration. The formation of isoindolones takes place in two steps with an aldehyde intermediate, which can be trapped with N,N-dimethylhydrazine.
dcterms:title
Unexpected course of rearrangement of substituted S-(1(3H)-isobenzofuranone-3-yl)isothiuronium bromides Unexpected course of rearrangement of substituted S-(1(3H)-isobenzofuranone-3-yl)isothiuronium bromides
skos:prefLabel
Unexpected course of rearrangement of substituted S-(1(3H)-isobenzofuranone-3-yl)isothiuronium bromides Unexpected course of rearrangement of substituted S-(1(3H)-isobenzofuranone-3-yl)isothiuronium bromides
skos:notation
RIV/00216275:25310/12:39894706!RIV13-MSM-25310___
n12:predkladatel
n13:orjk%3A25310
n3:aktivita
n18:P
n3:aktivity
P(EE2.3.30.0021)
n3:cisloPeriodika
47
n3:dodaniDat
n4:2013
n3:domaciTvurceVysledku
n10:4978684 n10:5804620 n10:1357727 n10:4889223
n3:druhVysledku
n17:J
n3:duvernostUdaju
n16:S
n3:entitaPredkladatele
n7:predkladatel
n3:idSjednocenehoVysledku
175963
n3:idVysledku
RIV/00216275:25310/12:39894706
n3:jazykVysledku
n8:eng
n3:klicovaSlova
Isothiuronium salt; Ring transformation; Mechanism; Rearrangement; S to N migration; CRYSTAL-STRUCTURES; S-ACYLISOTHIOUREAS; S(N)2 REACTIONS; RING TRANSFORMATION; GAS-PHASE; ACID-BASE CATALYSIS
n3:klicoveSlovo
n6:Ring%20transformation n6:Mechanism n6:GAS-PHASE n6:Rearrangement n6:Isothiuronium%20salt n6:S%20to%20N%20migration n6:CRYSTAL-STRUCTURES n6:ACID-BASE%20CATALYSIS n6:S%28N%292%20REACTIONS n6:S-ACYLISOTHIOUREAS n6:RING%20TRANSFORMATION
n3:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n3:kontrolniKodProRIV
[016967AD7871]
n3:nazevZdroje
Tetrahedron
n3:obor
n20:CC
n3:pocetDomacichTvurcuVysledku
4
n3:pocetTvurcuVysledku
4
n3:projekt
n15:EE2.3.30.0021
n3:rokUplatneniVysledku
n4:2012
n3:svazekPeriodika
68
n3:tvurceVysledku
Padělková, Zdeňka Váňa, Jiří Sedlák, Miloš Hanusek, Jiří
n3:wos
000310402400037
s:issn
0040-4020
s:numberOfPages
10
n5:doi
10.1016/j.tet.2012.09.005
n19:organizacniJednotka
25310