Stereoselective synthesis and structural study of derivatives of 2&#39;-benzoyl-1-benzyl-1&#39;-phenyl -1&#39;,2&#39;, 5&#39;,6&#39;,7&#39;,7a&#39;-hexahydrospiro [indolin-3,3&#39;-pyrrolizine]-2-one

Bilan Dmitri; Cojocari Sergiu; Barba Alic; Kravtsov Victor; Makaev Fliur

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2023-08-18 14:22

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BILAN, Dmitri, COJOCARI, Sergiu, BARBA, Alic, KRAVTSOV, Victor, MAKAEV, Fliur. Stereoselective synthesis and structural study of derivatives of 2'-benzoyl-1-benzyl-1'-phenyl -1',2', 5',6',7',7a'-hexahydrospiro [indolin-3,3'-pyrrolizine]-2-one. In: Achievements and perspectives of modern chemistry, 9-11 octombrie 2019, Chişinău. Chisinau, Republic of Moldova: Tipografia Academiei de Ştiinţe a Moldovei, 2019, p. 207. 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

Stereoselective synthesis and structural study of derivatives of 2'-benzoyl-1-benzyl-1'-phenyl -1',2', 5',6',7',7a'-hexahydrospiro [indolin-3,3'-pyrrolizine]-2-one

Pag. 207-207

Bilan Dmitri¹, Cojocari Sergiu¹, Barba Alic¹, Kravtsov Victor², Makaev Fliur¹

¹ Institute of Chemistry,
² Institute of Applied Physics

Disponibil în IBN: 11 noiembrie 2019

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Amides and amines play a central role in the control and modulation of virtually all biological processes. On the other side the inflexibility of the quaternary carbon of spirocycles locks the adjoined ring into a fixed 3-dimensional conformation such that it must receive some responsibility for its interaction with given receptors. Currently we have engaged ourselves in project aimed to define a one-pot protocol for the synthesis of highly functionalized spiro-oxindoles starting from corresponding a,b-enones, N-protected isatins andproline as well. We chose to synthesise the indolin-3 containing spirocycle, which provide a template for use in combinatorial chemistry. We have been able to demonstrate the versatility of 4a,b by derivatising the scaffold at each of its functional groups by use N-protected isatin 1, proline 2, and a,b-enones.formulaIn this report we demonstrate the stereoselectivity of [2+3] addition and crystal structure of two main products obtained by single crystal X-ray method.formulaCompounds 4a and 4b crystalize in centrosymmetric space groups, thus represent racemats. Space group and unit cell parameters for 4a are P-1, a=9.8449(7) b=12.552(1) c=12.6961(9)Å, a=115.561(8), b=97.134(6), z=101.279(7)º, V=1348.9(2)Å3 and for 4b P21/n,a=11.6456(7), b=11.6090(5), c=22.6398(9) Å, b =93.820(4)º, V=3054.0(2) Å3.

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<cfAbstr cfLangCode='EN' cfTrans='o'><p>Amides and amines play a central role in the control and modulation of virtually all biological processes. On the other side the inflexibility of the quaternary carbon of spirocycles locks the adjoined ring into a fixed 3-dimensional conformation such that it must receive some responsibility for its interaction with given receptors. Currently we have engaged ourselves in project aimed to define a one-pot protocol for the synthesis of highly functionalized spiro-oxindoles starting from corresponding a,b-enones, N-protected isatins andproline as well. We chose to synthesise the indolin-3 containing spirocycle, which provide a template for use in combinatorial chemistry. We have been able to demonstrate the versatility of 4a,b by derivatising the scaffold at each of its functional groups by use N-protected isatin 1, proline 2, and a,b-enones.</p><p>formula</p><p>In this report we demonstrate the stereoselectivity of [2+3] addition and crystal structure of two main products obtained by single crystal X-ray method.</p><p>formula</p><p>Compounds 4a and 4b crystalize in centrosymmetric space groups, thus represent racemats. Space group and unit cell parameters for 4a are P-1, a=9.8449(7) b=12.552(1) c=12.6961(9)&Aring;, a=115.561(8), b=97.134(6), z=101.279(7)&ordm;, V=1348.9(2)&Aring;3 and for 4b P21/n,a=11.6456(7), b=11.6090(5), c=22.6398(9) &Aring;, b =93.820(4)&ordm;, V=3054.0(2) &Aring;3.</p></cfAbstr>
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