Izmest'ev Alexei N, Gazieva Galina A, Sigay Natalya V, Serkov Sergei A, Karnoukhova Valentina A, Kachala Vadim V, Shashkov Alexander S, Zanin Igor E, Kravchenko Angelina N, Makhova Nina N
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, Russian Federation.
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str., 28, Moscow 119991, Russian Federation.
Beilstein J Org Chem. 2016 Oct 24;12:2240-2249. doi: 10.3762/bjoc.12.216. eCollection 2016.
An effective and highly regio- and diastereoselective one-pot method for the synthesis of new polynuclear dispiroheterocyclic systems with five stereogenic centers (dispiro[imidazo[4,5-]thiazolo[3,2-]-1,2,4-triazine-6,3'-pyrrolidine-2',3''-indoles]) comprising pyrrolidinyloxindole and imidazo[4,5-]thiazolo[3,2-]-1,2,4-triazine moieties has been developed. The method relies on a 1,3-dipolar cycloaddition of azomethine ylides generated in situ from isatin derivatives and sarcosine to 6-benzylideneimidazo[4,5-]thiazolo[3,2-]-1,2,4-triazine-2,7-diones.
已开发出一种有效且具有高度区域和非对映选择性的一锅法，用于合成具有五个立体中心的新型多核双螺杂环体系（双螺[咪唑并[4,5 - ]噻唑并[3,2 - ] - 1,2,4 - 三嗪 - 6,3'-吡咯烷 - 2',3'' - 吲哚]），该体系包含吡咯烷氧吲哚和咪唑并[4,5 - ]噻唑并[3,2 - ] - 1,2,4 - 三嗪部分。该方法基于由异吲哚酮衍生物和肌氨酸原位生成的甲亚胺叶立德与6 - 亚苄基咪唑并[4,5 - ]噻唑并[3,2 - ] - 1,2,4 - 三嗪 - 2,7 - 二酮的1,3 - 偶极环加成反应。
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