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利用液辅助磨盘化学,通过布朗斯台德酸催化的机械化学多组分反应级联反应。

Brønsted acid catalyzed mechanochemical domino multicomponent reactions by employing liquid assisted grindstone chemistry.

机构信息

School of Applied Material Sciences, Centre for Applied Chemistry, Sector-30, Central University of Gujarat, Gandhinagar, 382030, India.

Department of Chemistry, Central University of Punjab, Bathinda, 151401, India.

出版信息

Sci Rep. 2023 Jan 25;13(1):1386. doi: 10.1038/s41598-023-27948-y.

Abstract

Here, we have demonstrated a metal-free energy-efficient mechanochemical approach for expedient access to a diverse set of 2-amino-3-cyano-aryl/heteroaryl-4H-chromenes, tetrahydrospiro[chromene-3,4'-indoline], 2,2'-aryl/heteroarylmethylene-bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) as well as tetrahydro-1H-xanthen-1-one by employing the reactivity of 5,5-dimethylcyclohexane-1,3-dione/cyclohexane-1,3-dione with TsOH⋅HO as Brønsted acid catalyst under water-assisted grinding conditions at ambient temperature. The ability to accomplish multiple C-C, C=C, C-O, and C-N bonds from readily available starting materials via a domino multicomponent strategy in the absence of metal-catalyst as well as volatile organic solvents with an immediate reduction in the cost of the transformation without necessitates complex operational procedures, features the significant highlights of this approach. The excellent yield of the products, broad functional group tolerances, easy set-up, column-free, scalable synthesis with ultralow catalyst loading, short reaction time, waste-free, ligand-free, and toxic-free, are other notable advantages of this approach. The greenness and sustainability of the protocol were also established by demonstrating several green metrics parameters.

摘要

在这里,我们展示了一种无金属、节能的机械化学方法,通过使用 5,5-二甲基环己烷-1,3-二酮/环己烷-1,3-二酮与 TsOH⋅HO 作为布朗斯台德酸催化剂,在水辅助研磨条件下,在环境温度下从易得的起始原料中快速有效地获得各种 2-氨基-3-氰基-芳基/杂芳基-4H-色烯、四氢螺[色烯-3,4'-吲哚]、2,2'-芳基/杂芳基亚甲基-双(3-羟基-5,5-二甲基环己-2-烯酮)以及四氢-1H-呫吨-1-酮。该方法的显著特点是能够在无需金属催化剂和挥发性有机溶剂的情况下,通过多组分级联策略,从易得的起始原料中实现多个 C-C、C=C、C-O 和 C-N 键的形成,同时降低转化成本,无需复杂的操作程序。该方法还具有产物收率高、广泛的官能团容忍性、易于设置、无柱、可规模化合成、催化剂用量低、反应时间短、无废物、无配体和无毒性等优点。该方法还通过展示几个绿色指标参数,证明了其绿色和可持续性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/874e/9876939/a57fa50b0890/41598_2023_27948_Fig1_HTML.jpg

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