KSCN-mediated one-pot thiocyanation tandem cyclization of enaminones: a facile access to 2-amino/imino thiazolo fused chromone and coumarin frameworks

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2024-10-17 DOI:10.1002/ejoc.202400690
Akshay Kumawat, Sumbul Mansuri, Mary Sravani Galla, Nagula Shankaraiah
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Abstract

A rapid metal-free approach describing one-pot thiocyanation of chromone and coumarin enabling tandem cyclization via potassium thiocyanate as a sulfur surrogate was unveiled. Interestingly, this enaminone-mediated protocol facilitated straightforward access to medicinally significant 2-amino/imino thiazolo fused chromone and coumarin frameworks. This methodology provided good atom-economy, remarkable functional group tolerance, and scalability. Alongside establishing a wide substrate scope, it also provided a feasible scalability up to gram scale.
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KSCN 介导的烯氨酮一锅硫氰酸串联环化反应:轻松获得 2-氨基/亚氨基噻唑融合的铬酮和香豆素框架
该研究揭示了一种快速的无金属方法,即通过硫氰酸钾作为硫代物实现铬酮和香豆素的一锅硫氰酸化串联环化。有趣的是,这种由烯胺酮介导的方案有助于直接获得具有重要药用价值的 2-氨基/亚氨基噻唑并合铬酮和香豆素框架。这种方法具有良好的原子经济性、显著的官能团耐受性和可扩展性。在建立广泛的底物范围的同时,它还提供了高达克级的可行可扩展性。
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
期刊最新文献
A Chromium Catalytic System for the Synthesis of Aryl-Substituted 1,3,5-Triazines and Pyrimidines by Acceptorless Dehydrogenative Coupling Gilding the Lily: Studies on the Effects of Successive Loading of Light Energy‐Storing Molecules with Norbornadiene Units A Mechanistic Study of the Oxidation of Substituted Benzyl Alcohols with Trichloroisocyanuric Acid Convenient Synthesis of Dihydrobenzofuran-Fused Spirocyclopentane-1,2-Diindolinone Scaffolds KSCN-mediated one-pot thiocyanation tandem cyclization of enaminones: a facile access to 2-amino/imino thiazolo fused chromone and coumarin frameworks
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