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Synthesis, structure and cytotoxic activity of 2‐acetyl‐5‐trimethylsilylthiophene(furan) and their oximes
Author(s) -
Lukevics Edmunds,
Ignatovich Luba,
Sleiksha Ilze,
Muravenko Velta,
Shestakova Irina,
Belyakov Sergey,
Popelis Jury
Publication year - 2006
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1092
Subject(s) - chemistry , oxime , reagent , furan , hydrogen bond , intermolecular force , lithium (medication) , stereochemistry , medicinal chemistry , butyllithium , organic chemistry , molecule , medicine , endocrinology
Abstract 5‐Trimethylsilylderivatives of 2‐acetylthiophene and ‐furan have been regioselectively prepared by a one‐pot procedure from the corresponding 2‐acetylfuran or 2‐acetylthiophene using lithium N ‐methylpiperazide (LNMP)–butyllithium–trimethylchlorosilane–water as the sequence of reagents. The ketones obtained were converted to the corresponding oximes. The structure of 2‐acetyl‐5‐trimethylsilylthiophene oxime ( E ‐isomer) has been studied by X‐ray diffraction. Formation of centrosymmetric dimers by means of H‐bonds has been observed. The intermolecular hydrogen bond O9H…N8 length is 2.842(5) Å [H…N8 = 1.87 (6) Å, O9H…N8 = 157(4)°]. Copyright © 2006 John Wiley & Sons, Ltd.