Reaction of a brominated benzolactone/lactam with 4-methoxythiobenzamide and thiourea: an Eschenmoser coupling reaction, ring transformation, or dimerization?

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F15%3A39899681" target="_blank" >RIV/00216275:25310/15:39899681 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1016/j.tetlet.2015.03.052" target="_blank" >http://dx.doi.org/10.1016/j.tetlet.2015.03.052</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tetlet.2015.03.052" target="_blank" >10.1016/j.tetlet.2015.03.052</a>

Result language
angličtina
Original language name
Reaction of a brominated benzolactone/lactam with 4-methoxythiobenzamide and thiourea: an Eschenmoser coupling reaction, ring transformation, or dimerization?
Original language description
The reactions of 3-bromo-1-benzofuran-2(3H)-one (la) and 3-bromo-1,3-dihydro-2H-indo1-2-one (lb) with 4-methoxythiobenzamide and thiourea under mildly basic conditions are reported. While brominated lactone la gave the expected 5-(2-hydroxypheny1)-2-(4-methoxyphenyl)-1,3-thiazol-4-ol (2) or 2-amino-5-(2-hydroxyphenyl)-1,3-thiazol-4(5H)-one (5) products, the analogous brominated lactam lb reacted with the thioamide via an unexpected Eschenmoser coupling reaction to give (32)-3-[amino(4-methoxyphenyl)-methylidene]-1,3-dihydro-2H-indo1-2-one (3). When lactam lb was treated with thiourea, isoindigo (4) was the only isolated product. The reaction mechanisms, involving formation of alpha-thioiminium or isothiouronium salts and their base-catalyzed decomposition are also proposed.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
<a href="/en/project/EE2.3.30.0021" target="_blank" >EE2.3.30.0021: Strenthening of Research and Development Teams at the University of Pardubice</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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