Formation of 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones involving ring transformation of 2-aryl-5-(2-aminophenyl)-4-hydroxy-1,3-thiazoles
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F17%3A39910643" target="_blank" >RIV/00216275:25310/17:39910643 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1016/j.tet.2017.02.045" target="_blank" >http://dx.doi.org/10.1016/j.tet.2017.02.045</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tet.2017.02.045" target="_blank" >10.1016/j.tet.2017.02.045</a>
Alternative languages
Result language
angličtina
Original language name
Formation of 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones involving ring transformation of 2-aryl-5-(2-aminophenyl)-4-hydroxy-1,3-thiazoles
Original language description
The reaction of 3-bromooxindole with substituted (hetero)aromatic thioamides in acetonitrile was studied. At room temperature the reaction preferably gives products of ring transformation i.e. 2-aryl-5-(2-aminophenyl)-4-hydroxy-1,3-thiazoles (3b-f,h) whereas at elevated temperature products of an Eschenmoser coupling reaction, i.e. 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones (2b-f), are formed exclusively. There exist only two exceptions (4-methoxy and 2-pyridinthioamide) in which the Eschenmoser coupling reaction always takes place giving 2a and 2g. Also N-methylation of the starting 3-bromooxindole completely prevents formation of thiazoles. The prepared thiazoles 3b-f are unstable in solution and they undergo slow ring transformation to 2b-f. The rate limiting step of this rearrangement involves cleavage of an intermediary thiirane ring, which is slowed down by electron withdrawing substituents on the thioamide (rho = -1.15).
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
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Continuities
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Tetrahedron
ISSN
0040-4020
e-ISSN
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Volume of the periodical
73
Issue of the periodical within the volume
14
Country of publishing house
GB - UNITED KINGDOM
Number of pages
6
Pages from-to
1861-1866
UT code for WoS article
000396958700010
EID of the result in the Scopus database
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