- Copper-Catalyzed Ring Opening of Benzofurans and an Enantioselective Hydroamination Cascade
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A copper(II) acetate/(R)-DTBM-SEGPHOS-catalyzed ring opening of benzofurans and enantioselective hydroamination cascade with dimethoxymethylsilane (DMMS) and hydroxylamine esters is described. Starting from readily available substituted benzofurans, a series of chiral N,N-dibenzylaminophenols, which are of high interest in pharmaceutical chemistry, were obtained with excellent enantioselectivities (up to 66 % yield, 94 % ee).
- Xu-Xu, Qing-Feng,Liu, Qiang-Qiang,Zhang, Xiao,You, Shu-Li
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- Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers
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We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.
- Delcaillau, Tristan,Boehm, Philip,Morandi, Bill
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supporting information
p. 3723 - 3728
(2021/04/07)
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- PREPARATION AND CYCLIZATION OF ARYLOXYACETALDEHYDE ACETALS; A GENERAL SYNTHESIS OF 2,3-UNSUBSTITUTED BENZOFURANS
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A improved method for the preparation of 2,3-unsubstituted benzofurans is described.Specifically, the PPA catalysed cyclization of aryloxyacetaldehyde acetals to give (4-7)-substituted benzofurans has been achieved.
- Barker, Peter,Finke, Paul,Thompson, Kevan
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p. 257 - 266
(2007/10/02)
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- Bronchodilator and Antiulcer Phenoxypyrimidinones
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Series of 5-phenoxy-2(1H)-pyrimidinones, 5-phenoxy-4(3H)-pyrimidinones, and related compounds were prepared in a follow-up of a lead prepared as a potential cyclic nucleotide regulating agent.Compounds were evaluated for bronchodilator activity in histamine-challenged guinea pigs and for antiulcer activity in a cold-restraint, stressed rat ulcer model.Bronchodilator activity comparable to, or greater than, that of theophylline was found in both the 2(1H)- and 4(3H)-pyrimidinone series and was most prominent in analogues containing either an electron-withdrawing or -donating substituent in the para position of the phenoxy ring.Significant antiulcer activity was observed only in the 2(1H)-pyrimidinone series among three closely related analogues.One of these, 5-(m-methylphenoxy)-2(1H)-pyrimidinone (3), exhibited more potent antiulcer effects than the clinically useful antiulcer agent carbenoxolone, without demonstrating bronchodilator activity.
- Lipinski, C. A.,Stam, J. G.,Pereira, J. N.,Ackerman, N. R.,Hess, H.-J.
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p. 1026 - 1031
(2007/10/02)
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- 1-Alkyl-2-(phenoxymethyl)-5-nitro-imidazoles and process for their manufacture
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1-Alkyl-2-(phenoxymethyl)-5-nitro-imidazoles are described as well as a process for their manufacture. The compounds are active against trichomonads and amoebae and are especially suitable for the treatment of Fluor genitalis.
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