Synthesis of enatiomerically pure highly functionalised spiro-[indolin-3,3'-pyrrolizin]-2-ones
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BILAN, Dmitri; COJOCARI, Serghei; GORINCIOI, Elena; KRAVTSOV, Victor; MACAEV, Fliur. Synthesis of enatiomerically pure highly functionalised spiro-[indolin-3,3'-pyrrolizin]-2-ones. In: Achievements and perspectives of modern chemistry. 9-11 octombrie 2019, Chişinău. Chisinau, Republic of Moldova: Tipografia Academiei de Ştiinţe a Moldovei, 2019, p. 208. ISBN 978-9975-62-428-2.
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Achievements and perspectives of modern chemistry 2019
Conferința "International Conference "Achievements and perspectives of modern chemistry""
Chişinău, Moldova, 9-11 octombrie 2019

Synthesis of enatiomerically pure highly functionalised spiro-[indolin-3,3'-pyrrolizin]-2-ones


Pag. 208-208

Bilan Dmitri1, Cojocari Serghei1, Gorincioi Elena1, Kravtsov Victor2, Macaev Fliur1
 
1 Institute of Chemistry,
2 Institute of Applied Physics
 
Disponibil în IBN: 11 noiembrie 2019


Rezumat

Number of spiro-derivatives of isatin has biological activity and some have been isolated from natural sources. A cycloaddition reaction of unsaturated molecules with parts of the other molecule, can serve as versatile building blocks of a number of important and often novel bioactive compounds. In presentation will include methodology enhancement for generation of novel spiroindolin3,3'-pyrrolizin]-2-onesscaffolds and application to the synthesis and study of enatiomerically pure indolin-3,3'-pyrrolizin]-2-ones 4.formulaMethodology has included N-benzylisatine 1, trans-4-hydroxyproline 2 and chalcone 3. The results of the modeling and NMR study of the compounds will also be discussed. The structure of 4 has been confirmed by single crystal X-ray method. Compound crystalizes in orthorhombic non-centrosymmetric space groups P212121, thus represent pure enantiomer, a = 9.1612(6), b = 10.5824(8), c = 28.393(2) Å, V =2752.7(3) Å3. Bond distances O1-1 1.215(5) and O2-C 1.208(6)Å unambiguously indicates double bonds while O3-C 1.411(5) single one. The sum of bond angles at N1 atom equals 360.1º and shows planar configuration whereas the sum of bond angles at N2 atom equals 343.2º and indicates some degree of its pyramidality.formulaIn the crystal O3-H…O1 2.982Å hydrogen bonds unite molecules of 4 in infinite lefthanded helix along crystallographic axis a.