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使用L-脯氨酸功能化的锰铁氧体纳米棒作为新型多相催化剂立体选择性合成螺环吡咯烷/吡咯里西啶/吡咯并噻唑烷

Stereoselective synthesis of spirocyclic pyrrolidines/pyrrolizidines/pyrrolothiazolidines using l-proline functionalized manganese ferrite nanorods as a novel heterogeneous catalyst.

作者信息

Akhavan Malihe, Bekhradnia Ahmadreza

机构信息

Pharmaceutical Sciences Research Centre, Department of Medicinal Chemistry, Mazandaran University of Medical Sciences Sari Iran

Department of Chemistry and Biochemistry, 103CBB, Montana State University Bozeman MT 59717 USA.

出版信息

RSC Adv. 2021 Apr 20;11(24):14755-14768. doi: 10.1039/d1ra00841b. eCollection 2021 Apr 15.

Abstract

An efficient, green, one-pot, and three-component protocol has been reported for the stereoselective synthesis of a new class of spiro thiazolidines. A series of spiro-heterocycle derivatives were produced stereoselectively in high yields by the reaction of 5-arylidene thiazolidine-2,4-diones, isatin, and secondary amino acids in the presence of MnCoCuFeO@l-proline (MCCFeO@l-proline) magnetic nanorods as a novel nanocatalyst. The synthesized catalyst was fully characterized for thermal stability, magnetic properties, and other physicochemical properties numerous techniques. It was applied as an efficient and reusable catalyst for the synthesis of -isomers of spirocyclic pyrrolidine/pyrrolizidine/pyrrolothiazolidine derivatives in high yield. The regioselectivity and stereochemistry of these heterocyclic spiro-compounds were established by H, C, HMBC, HSQC, and COSY NMR spectroscopy techniques. The main attractive characteristics of the presented protocol are high yield, high level of diastereoselectivity, and easy recovery of catalyst without significant loss of its catalytic activity.

摘要

据报道,一种高效、绿色、一锅法和三组分的方法可用于立体选择性合成一类新型螺噻唑烷。在新型纳米催化剂MnCoCuFeO@l-脯氨酸(MCCFeO@l-脯氨酸)磁性纳米棒存在下,通过5-亚芳基噻唑烷-2,4-二酮、异吲哚酮和仲氨基酸的反应,一系列螺杂环衍生物以高产率立体选择性地生成。通过多种技术对合成的催化剂进行了全面表征,以确定其热稳定性、磁性和其他物理化学性质。它被用作一种高效且可重复使用的催化剂,用于高产率合成螺环吡咯烷/吡咯里西啶/吡咯噻唑烷衍生物的β-异构体。这些杂环螺化合物的区域选择性和立体化学通过1H、13C、HMBC、HSQC和COSY核磁共振光谱技术确定。所提出方法的主要吸引人的特点是高产率、高非对映选择性以及催化剂易于回收且其催化活性无明显损失。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4609/8698206/75d9a5e1d0f1/d1ra00841b-f1.jpg

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