Synthesis and reactions of 1-hydroxy-9,9a-dihydro-1H-imidazo[1,2-a]indol-2(3H)-ones

TETRAHEDRON

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Article

Martynaitis, Vytas¹  Steponaviciute, Rasa¹  Krikstolaityte, Sonata¹  Solovjova, Joana²  Mangelinckx, Sven³  De Kimpe, Norbert³  Holzer, Wolfgang⁴  Sackus, Algirdas^1,2 

[1] Kaunas Univ Technol, Dept Organ Chem, LT-50270 Kaunas, Lithuania

[2] Kaunas Univ Technol, Inst Synthet Chem, LT-50270 Kaunas, Lithuania

[3] Univ Ghent, Fac Biosci Engn, Dept Sustainable Organ Chem & Technol, B-9000 Ghent, Belgium

[4] Univ Vienna, Dept Drug Synth, Fac Life Sci, A-1090 Vienna, Austria

关键词: Hydroxamic acids;    Indolium salts;    Imidazolidinones;    Ring opening;   

DOI  :  10.1016/j.tet.2011.03.044

来源: Elsevier

【 摘 要 】

1-Hydroxy-9,9a-dihydro-1H-imidazo[1,2-alindol-2(3H)-ones, as a new type of azaheterocyclic hydroxamic acids, have been synthesized regioselectively from 1-carbamoylmethyl- or 1-(methoxycarbonyl) methyl-2,3,3-trimethyl-3H-indolium salts by reaction with hydroxylamine in the presence of a strong base. The alkylation and reduction with sodium borohydride of these novel heterocycles have been investigated. When treated with protic acids 1-hydroxy- or 1-alkoxy-9,9a-dihydro-1H-imidazo[1,2-alindol-2(3H)-ones underwent ring opening of the imidazolidine to afford 1-[2-(hydroxyamino)-2-oxoethyl]-2,3,3-trimethyl-3H-indolium salts. The structural assignments are based on extensive H-1,C-13 and N-15 NMR spectroscopic studies and single crystal X-ray analyses. (C) 2011 Elsevier Ltd. All rights reserved.

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