About: Unexpected course of rearrangement of substituted S-(1(3H)-isobenzofuranone-3-yl)isothiuronium bromides

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About: Unexpected course of rearrangement of substituted S-(1(3H)-isobenzofuranone-3-yl)isothiuronium bromides Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
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. (en)
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 (en)
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 (en)
skos:notation	RIV/00216275:25310/12:39894706!RIV13-MSM-25310___
http://linked.open...avai/riv/aktivita	P
http://linked.open...avai/riv/aktivity	P(EE2.3.30.0021)
http://linked.open...iv/cisloPeriodika	47
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Padělková, Zdeňka Sedlák, Miloš Hanusek, Jiří Váňa, Jiří
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Pardubice / Fakulta chemicko-technologická
http://linked.open...dnocenehoVysledku	175963
http://linked.open...ai/riv/idVysledku	RIV/00216275:25310/12:39894706
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/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 (en)
http://linked.open.../riv/klicoveSlovo	Mechanism GAS-PHASE CRYSTAL-STRUCTURES Rearrangement ACID-BASE CATALYSIS Isothiuronium salt RING TRANSFORMATION Ring transformation S to N migration S(N)2 REACTIONS S-ACYLISOTHIOUREAS
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[016967AD7871]
http://linked.open...i/riv/nazevZdroje	Tetrahedron
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	4 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...vavai/riv/projekt	Strenthening of Research and Development Teams at the University of Pardubice
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	68
http://linked.open...iv/tvurceVysledku	Padělková, Zdeňka Váňa, Jiří Sedlák, Miloš Hanusek, Jiří
http://linked.open...ain/vavai/riv/wos	000310402400037
issn	0040-4020
number of pages	10 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.tet.2012.09.005
http://localhost/t...ganizacniJednotka	25310

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