Login for students

Login for employees

Publication detail

Reaction of a brominated benzolactone/lactam with 4-methoxythiobenzamide and thiourea: an Eschenmoser coupling reaction, ring transformation, or dimerization?
Authors: Kammel Richard | Tarabová Denisa | Růžičková Zdeňka | Hanusek Jiří
Year: 2015
Type of publication: článek v odborném periodiku
Name of source: Tetrahedron Letters
Publisher name: Pergamon-Elsevier Science Ltd.
Place: Oxford
Page from-to: 2548-2550
Titles:
Language Name Abstract Keywords
cze Reakce bromovaného benzolaktonu/laktamu s 4-methoxythiobenzamidem a thiomočovinou: Eschenmoserova reakce, transformace kruhu nebo dimerizace? Byly popsány reakce 3-brom-1-benzofuran-2(3H)-onu (la) a 3-brom-1,3-dihydro-2H-indol-2-onu (lb) s 4-methoxythiobenzamidem a thiomočovinou za mírně bazických podmínek. Zatímco bromovaný lakton la poskytuje očekávaný 5-(2-hydroxyfeny1)-2-(4-methoxyfenyl)-1,3-thiazol-4-ol (2) nebo 2-amino-5-(2-hydroxyfenyl)-1,3-thiazol-4(5H)-on (5), analogický bromovaný laktam lb reaguje s thioamidem neočekávanou Eschenmoserovou reakcí za vzniku (3Z)-3-[amino(4-methoxyfenyl)-methyliden]-1,3-dihydro-2H-indol-2-onu (3). Když laktam lb reaguje s thiomočovinou, tvoří se isoindigo (4). Reakční mechanismus zahrnuje tvorbu alfa-thioiminiové soli nebo isothiouroniové soli a jejich bazicky katalyzovaný přesmyk. transformace kruhu; Eschenmoserova reakce; 3-Brom-1,3-dihydro-2H-indol-2-on; 3-Brom-1-benzofuran-2(3H)-on
eng Reaction of a brominated benzolactone/lactam with 4-methoxythiobenzamide and thiourea: an Eschenmoser coupling reaction, ring transformation, or dimerization? 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. Ring transformation; Eschenmoser coupling reaction; 3-Bromo-1,3-dihydro-2H-indo1-2-one; 3-Bromo-1-benzofuran-2(3H)-one

Departments

Other Parts

Map

en.mapy.cz

Services

Popular Links

© 2023 University of Pardubice, Studentská 95, 532 10 Pardubice 2
Phone: +420 466 036 111, 466 036 112, 466 036 113
Webmaster, RSS
Data box ID: f5vj9hu
Accessibility Statement
CC BY-NC-ND 4.0Creative CommonsAttributionNonCommercialNoDerivatives