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通过基于异吲哚酮的三组分反应合成新型螺[色烯并[2,3 - d][1,3,4]噻二唑并[3,2 - a]嘧啶]

Synthesis of novel spiro[chromeno[2,3-d][1,3,4]thiadiazolo[3,2-a] pyrimidines via an isatin-based three-component reaction.

作者信息

Khalili Maryam, Esmaeili Abbas Ali

机构信息

Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, P.O.Box 9177948974, Mashhad, Iran.

出版信息

Sci Rep. 2025 May 12;15(1):16490. doi: 10.1038/s41598-025-00461-0.

DOI:10.1038/s41598-025-00461-0
PMID:40355461
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12069610/
Abstract

This study presents an efficient and sustainable method for the synthesis of novel spiro[chromeno[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidine-10,3'-indoline]-2',9,11-trione derivatives via a three-component condensation reaction is introduced. The reaction involves dimedone, 5H-[1,3,4]thiadiazolo[3,2-a]pyrimidine-5,7(6 H)-dione, and isatin derivatives, catalyzed by the economical and highly effective Keggin heteropolyacid (H₃PW₁₂O₄₀). This protocol achieves (70-90%) yields within relatively short reaction times under mild and solvent-free conditions. Using a green, cost-effective catalyst highlights the method's practicality and potential for broader applications in synthetic organic chemistry, offering an attractive route for spiro oxindole derivative synthesis.

摘要

本研究提出了一种高效且可持续的方法,通过引入三组分缩合反应来合成新型螺[色烯并[2,3 - d][1,3,4]噻二唑并[3,2 - a]嘧啶 - 10,3'-吲哚啉]-2',9,11 - 三酮衍生物。该反应涉及达米酮、5H - [1,3,4]噻二唑并[3,2 - a]嘧啶 - 5,7(6H)-二酮和异吲哚酮衍生物,由经济高效的Keggin杂多酸(H₃PW₁₂O₄₀)催化。该方案在温和且无溶剂的条件下,在相对较短的反应时间内实现了(70 - 90%)的产率。使用绿色、经济高效的催化剂突出了该方法在合成有机化学中的实用性和更广泛应用的潜力,为螺环氧化吲哚衍生物的合成提供了一条有吸引力的途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ee91/12069610/2ee684a13146/41598_2025_461_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ee91/12069610/1390c9a3575d/41598_2025_461_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ee91/12069610/6ab1ecda9e46/41598_2025_461_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ee91/12069610/5939b308485c/41598_2025_461_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ee91/12069610/f45bac040f5e/41598_2025_461_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ee91/12069610/2ee684a13146/41598_2025_461_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ee91/12069610/1390c9a3575d/41598_2025_461_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ee91/12069610/6ab1ecda9e46/41598_2025_461_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ee91/12069610/5939b308485c/41598_2025_461_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ee91/12069610/f45bac040f5e/41598_2025_461_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ee91/12069610/2ee684a13146/41598_2025_461_Sch2_HTML.jpg

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