The molecular and crystal stucture data for aminoderivative of (3E)-3-(2-oxo-2-phenylethylidene)-1,3-dihydro-2H-indol-2-one
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ZVEAGHINTSEVA, Marina, SUCMAN, Natalia, MAKAEV, Fliur. The molecular and crystal stucture data for aminoderivative of (3E)-3-(2-oxo-2-phenylethylidene)-1,3-dihydro-2H-indol-2-one. In: Materials Science and Condensed Matter Physics, Ed. 9, 25-28 septembrie 2018, Chișinău. Chișinău, Republica Moldova: Institutul de Fizică Aplicată, 2018, Ediția 9, p. 161.
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Materials Science and Condensed Matter Physics
Ediția 9, 2018
Conferința "International Conference on Materials Science and Condensed Matter Physics"
9, Chișinău, Moldova, 25-28 septembrie 2018

The molecular and crystal stucture data for aminoderivative of (3E)-3-(2-oxo-2-phenylethylidene)-1,3-dihydro-2H-indol-2-one

CZU: 547.7

Pag. 161-161

Zveaghintseva Marina, Sucman Natalia, Makaev Fliur
 
Institute of Chemistry
 
 
Disponibil în IBN: 6 februarie 2019


Rezumat

Oxindole moiety is widely represented in a huge amount of alkaloids and biologically active molecules [1-3]. In the last decade organic chemists, attracted by the broad pharmacological activities of compounds containing this scaffold, have developed a lot of synthetic strategies to obtain versatile derivatives. In connection with our ongoing research towards the convenient synthesis of both natural products and industrially relevant molecules [4-6], we were interested in the synthesis of the nitrogen substituted oxindoles via direct amination as key transformation. For this purpose, we carried out a delicate amination of (3E)-3-(2-oxo-2-phenylethylidene)-1,3- dihydro-2H-indol-2-one 1 by the quaternary aminotriazolium salt according to the procedure [7]. Herein, the compound, named (3Z)-3-(1-amino-2-oxo-2-phenylethylidene)-1,3-dihydro-2H-indol-2- one 2, has been isolated by column chromatography as oil. The solution in MeOH was left to crystallize slowly at room temperature then filtered off to obtained small red crystals and structure has been assigned on the basis of its elemental analysis, IR, NMR, single crystal X-Ray diffraction study.  In conclusion, we have developed a useful and versatile synthetic protocol for the preparation of amine substituted 3-alkylidene oxindole. The results obtained may be useful for synthetic organic as well combinatorial chemistry.