47223-94-9Relevant academic research and scientific papers
2,3-disubstituted indoline compound as well as preparation method and application thereof
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, (2020/06/24)
The invention discloses a preparation method of a 2,3-disubstituted indoline compound, as well as a preparation method and application thereof. A tert-butyl sulfonyl (Bus) protected imine-alkyne aminecompound shown as a formula I and aryl boronic acid are used as raw materials; according to the preparation method, high-regioselectivity arylation cyclization is realized under mild reaction conditions in the presence of a cheap copper catalyst, and various 2,3-disubstituted indoline compounds are conveniently prepared at medium to excellent yield, and have a wide substrate application range andgroup tolerance. The 2,3-disubstituted indoline compound can be conveniently made into various useful 2-benzyl-1H-indole compounds and indolyl methanol compounds.
Copper-catalyzed tandemcis-carbometallation/cyclization of imine-ynamides with arylboronic acids
Wang, Hao-Ran,Huang, En-He,Luo, Chen,Luo, Wen-Feng,Xu, Yin,Qian, Peng-Cheng,Zhou, Jin-Mei,Ye, Long-Wu
, p. 4832 - 4835 (2020/05/13)
An efficient copper-catalyzed tandem regioselectivecis-carbometallation/cyclization of imine-ynamides with arylboronic acids has been developed. This method leads to a facile and practical synthesis of valuable 2,3-disubstituted indolines in moderate to e
Lithiation of 1-alkoxyindole derivatives
Nakagawa, Kyoko,Kobayashi, Tetsuya,Kawasaki, Toshiya,Somei, Masanori
, p. 968 - 997 (2019/04/26)
Lithiation of 1-alkoxyindoles, 3-dimethylaminomethyl- and 3-dimethylaminoethyl-1-methoxyindole occurred regioselectively at the 2-position. The introduction of a sterically bulky group into the 2-position of 3-dimethylaminomethyl-1-methoxyindoles directed the lithiation to the 4-position.
Intramolecular addition of benzylic radicals onto ketenimines. Synthesis of 2-alkylindoles
Alajarin, Mateo,Vidal, Angel,Ortin, Maria-Mar
, p. 4282 - 4292 (2007/10/03)
The inter- and intramolecular addition of free radicals onto ketenimines is studied. All the attempts to add intermolecularly several silicon, oxygen or carbon centered radicals to N-(4-methylphenyl)-C,C-diphenyl ketenimine were unsuccessful. In contrast, the intramolecular addition of benzylic radicals, generated from xanthates, onto the central carbon of a ketenimine function with its N atom linked to the ortho position of the aromatic ring occurred under a variety of reaction conditions. These intramolecular cyclizations provide a novel radical-mediated synthesis of 2-alkylindoles.
First radical addition onto ketenimines: A novel synthesis of indoles
Alajarin, Mateo,Vidal, Angel,Ortin, Maria-Mar
, p. 3027 - 3030 (2007/10/03)
A novel radical-mediated synthesis of 2-alkyl indoles is described. The method is a nonchain process based on the intramolecular addition of benzylic radicals onto the central carbon atom of a ketenimine function, resulting in a 5-exo-dig cyclization.
A REGIOSELECTIVE LITHIATION OF 1-METHOXYMETHOXYINDOLE AT THE 2-POSITION AND ITS APPLICATION FOR THE SYNTHESIS OF 2-SUBSTITUTED INDOLES
Somei, Masanori,Kobayashi, Tetsuya
, p. 1295 - 1298 (2007/10/02)
A regioselective lithiation of 1-methoxymethoxyindole at the 2-position was achieved with n-BuLi at 0 deg C.Subsequent treatment with electrophiles afforded 2-substituted 1-methoxymethoxyindoles, which were readily converted to 2-substituted indoles.
PREPARATION OF 1-HYDROXYINDOLE DERIVATIVES AND A NEW ROUTE TO 2-SUBSTITUTED INDOLES
Kawasaki, Toshiya,Kodama, Atsushi,Nishida, Tokiko,Shimizu, Kazuhisa,Somei, Masanori
, p. 221 - 227 (2007/10/02)
An easy handling method of 1-hydroxyindole is developed.Based on the method, preparation and reaction of 1-hydroxyindole derivatives are investigated.A new regioselective lithiation of 1-methoxyindole and its application for the synthesis of 2-substituted indoles are also reported.
