用 α-芳香族酮类化合物合成 ISOFLAVONES 的无毡和无金属结构物

IF 2.8 4区 化学 Q1 CHEMISTRY, ORGANIC
Omkar Bains , Ashish Kumar , Raj Kamal , Ravinder Kumar , Rajesh Kumar , Tanmay Rom , Avijit Kumar Paul
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引用次数: 0

摘要

考虑到现有异黄酮合成方法的缺点,我们在此报告了一种无金属、环保的方法来合成这些天然产品。在本研究中,我们采用 α-芳基-β,β-二丁氧基酮协议合成了 8 种异黄酮衍生物 7a-7h。首先,我们对各查尔酮分子的 2'-羟基进行了保护,以消除其在反应条件下的干扰。然后,在非亲核溶剂(CH2Cl2)中用羟基(对甲苯磺酰氧基)碘苯(HTIB)试剂处理受 2'- 保护的查尔酮,使其发生 1,2-芳基迁移。通过这种迁移,相应的查耳酮通过 C-C 键形成了 α-芳基-β,β-二丁氧基酮,收率为中等到良好(55%-82%)。通过单晶 X 射线衍射数据,研究了 α-芳基-β,β-二丁氧基酮确切分子结构的模糊性。最后,α-芳基-β,β-二丁氧基酮与氢氧化钠在甲醇水溶液中发生反应,合成了异黄酮,收率为中等到良好(50-80%)。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Facile and Metal‐Free Synthesis of Isoflavones Using α‐Aryl‐β,β‐Ditosyloxy Ketones
Considering the drawbacks associated with available synthetic methodologies of isoflavones, herein we have reported a metal‐free and eco‐friendly approach to these natural products. In the present study, we have carried out the synthesis of eight isoflavone derivatives 7a7h using α‐aryl‐β,β‐ditosyloxy ketone protocol. Initially, we have protected the 2’‐hydroxy group of respective chalcone moiety in order to remove its interference under reaction conditions. The protected chalcones were then subjected to 1,2‐aryl migration by being treated with hydroxy(tosyloxy)iodobenzene (HTIB) reagent in a non‐nucleophilic solvent (CH2Cl2). This migration furnished the formation of α‐aryl‐β,β‐ditosyloxy ketones via C−C bond formation from their corresponding chalcones in moderate to good yields (55–82 %). The ambiguity regarding the exact molecular structure of the α‐aryl‐β,β‐ditosyloxy ketones was examined through the single crystal X‐ray diffraction data. At last, the synthesis of isoflavones was carried out in moderate to good yields (50–80 %) by performing the reaction of α‐aryl‐β,β‐ditosyloxy ketones with sodium hydroxide in aqueous methanol.
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来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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