Literature DB >> 23538780

BF3·OEt2-Promoted Concise Synthesis of Difluoroboron-Derivatized Curcumins from Aldehydes and 2,4-Pentanedione.

Kai Liu1, Jiangmin Chen, Jeremy Chojnacki, Shijun Zhang.   

Abstract

A concise and one-pot cascade method has been developed to achieve the synthesis of difluoroboron-derivatized curcumins (BF2C). Treatment of 2,4-pentanedione with BF3·OEt2, followed by condensation with aldehydes in the presence of tributyl borate and butylamine at 65 °C in toluene furnished the corresponding symmetric (s-BF2C) and unsymmetric difluoroboron-derivatized curcumins (us-BF2C) in good (60 - 99%) and moderate yields (23 - 42%) within 6 - 12 h, respectively.

Entities:  

Keywords:  BF3-Et2O promoted reaction; Curcumin analog; concise synthesis; difluoroboron complex

Year:  2013        PMID： 23538780      PMCID： PMC3607379          DOI： 10.1016/j.tetlet.2013.02.015

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  16 in total

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9.  Design, synthesis, and testing of difluoroboron-derivatized curcumins as near-infrared probes for in vivo detection of amyloid-beta deposits.

Authors:  Chongzhao Ran; Xiaoyin Xu; Scott B Raymond; Brian J Ferrara; Krista Neal; Brian J Bacskai; Zdravka Medarova; Anna Moore
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Review 10.  Turmeric--chemistry, technology, and quality.

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2.  Photophysical and Photoacoustic Properties of π-Extended Curcumin Dyes. Effects of the Terminal Dimethylamino Electron-donor and the Bridging Aryl Ring.

Authors:  Raymond E Borg; Maryam Hatamimoslehabadi; Stephanie Bellinger; Jeffrey La; Farha Mithila; Chandra Yelleswarapu; Jonathan Rochford
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5.  Hybrid Synthetic and Computational Study of an Optimized, Solvent-Free Approach to Curcuminoids.

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6.  Curcuminoid-BF2 complexes: Synthesis, fluorescence and optimization of BF2 group cleavage.

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  6 in total

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