Tropone hydrazides in [10+2]-hetero-higher-order cycloaddition for the synthesis of tetrahydropyridazine derivatives

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-10-08 DOI:10.1002/adsc.202401033

Adam Cieśliński, Artur Przydacz, Lesław Sieroń, Anna Skrzyńska, Łukasz Albrecht

引用次数: 0

Abstract

[10+2]-Hetero-higher-order cycloaddition between tropone hydrazides (acting as 10π-components) and 3-alkylidene oxindoles (acting as 2π-components) has been established. Under Brønsted base catalysis the reaction proceeded in a fully peri- and diastereoselective manner with the stereochemical outcome governed mainly by electronic interactions. Following such a strategy, a series of structurally diverse tetrahydropyridazines were prepared in 30-70% yields. Furthermore, the potential of the obtained cycloadducts has been confirmed in selected chemoselective transformations.

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用于合成四氢哒嗪衍生物的 [10+2]-hetero-higher-order cycloaddition 中的托品酰肼

在托品酮酰肼（作为 10π 组份）和 3-亚烷基羰基吲哚（作为 2π 组份）之间建立了 [10+2]- 异高阶环加成反应。在布氏碱催化下，反应以完全对映和非对映选择性的方式进行，立体化学结果主要受电子相互作用的影响。按照这种策略，制备出了一系列结构不同的四氢哒嗪，产率为 30-70%。此外，在选定的化学选择性转化过程中，所获得的环加合物的潜力也得到了证实。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.