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The alkylation of isatin-derived oximes: Spectroscopic and X-ray crystallographic structural characterization of oxime and nitrone products

✍ Scribed by Ny Sin; Brian L. Venables; Xiaohong Liu; Stella Huang; Qi Gao; Alicia Ng; Richard Dalterio; Ramkumar Rajamani; Nicholas A. Meanwell

Publisher
Journal of Heterocyclic Chemistry
Year
2009
Tongue
English
Weight
174 KB
Volume
46
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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A series of isatin oximes was alkylated with alkyl halides and under Mitsunobu conditions to generate O‐alkylated oxime ether and N‐alkylated nitrone products. Alkylation of the sodium salts of oximes 5a and 5b with alkyl iodides produced predominantly the N‐alkylated nitrones (E)‐7 while alkylation of 5a and 5b with the harder electrophiles alkyl bromides and alkyl chlorides, gave mostly the O‐alkylated products, oxime ethers (E)‐6. Interestingly, alkylation of oxime 5b under Mitsunobu conditions with isopropyl alcohol produced the N‐alkylated nitrone (E)‐7bd as the major product. However, alkylation of oxime 5c, which incorporates a sterically bulky bromine substituent at the C‐4 position of the isatin heterocycle, with 2‐bromo‐ and 2‐iodo‐propane or with isopropyl alcohol under Mitsunobu conditions gave exclusively the O‐alkylated product, oxime ether (Z)‐6cd. The oxime ether and nitrone products (E)‐6 and (E)‐7, respectively, were characterized by LC/MS, ^1^H NMR, and ^13^C NMR. In addition, the structures of oxime ether (E)‐6bd and nitrone (E)‐7ad were determined by X‐ray crystallography. J. Heterocyclic Chem., 46, 432 (2009).

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