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Unexpected course of rearrangement of substituted S-(1(3H)-isobenzofuranone-3-yl)isothiuronium bromides
Year: 2012
Type of publication: článek v odborném periodiku
Name of source: Tetrahedron
Publisher name: Pergamon-Elsevier Science Ltd.
Place: Oxford
Page from-to: 9808-9817
Titles:
Language Name Abstract Keywords
cze Neočekávaný průběh přesmyku substituovaných S-(1(3H)-isobenzofuranon-3-yl)isothiouronium-bromidů Tři serie S-(1(3H)-isobenzofuranon-3-yl)isothiuronium-bromidů lišící se v substituci isothiuroniové části (žádný, jedna nebo dvě methyl skupiny) a na benzenovém jádře byly připraveny a charakterizovány. Tyto soli byly ponechány reagovat s různými bázemi (acetát, triethylamin, Na2CO3) za vzniku buď 1-hydroxy-3-oxo-1,3-dihydro-2H-isoindol-2-karbothioamidů nebo produktů S na N migrace isobenzofuranon-3-ylového zbytku, tj. 1,3-dimethyl-1-(3-oxo-1,3-dihydro-2-benzofuran-1-yl)thiomočovin. Pokud byl použit amoniak a N,N'-dimethyl isothiuroniová sůl, vznikal 3-hydroxy-2,3-dihydro-1H-isoindol-1-on spolu s 1,3-dimethyl-1-(3-oxo-1,3-dihydro-2-benzofuran-1-yl)thiomočovinou v paralelní reakci ve výtěžcích rostoucích s koncetrací amoniaku. Tvorba isoindolonů probíhá ve dvou krocích přes aldehydový intermediát, který lze zachytit reakcí s N,N-dimethylhydrazinem. přesmyk; S-1(3H-isobenzofuranon-3-yl)isothiouronium-bromid; S na N migrace
eng Unexpected course of rearrangement of substituted S-(1(3H)-isobenzofuranone-3-yl)isothiuronium bromides 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. ACID-BASE CATALYSIS; GAS-PHASE; RING TRANSFORMATION; S(N)2 REACTIONS; S-ACYLISOTHIOUREAS; CRYSTAL-STRUCTURES; S to N migration; Rearrangement; Mechanism; Ring transformation; Isothiuronium salt

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