Fast Method for Synthesis of Alkyl and Aryl-N-Methylnitrones.docVIP

Molecules 2011, 16, 6677-6683; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Fast Method for Synthesis of Alkyl and Aryl-N-Methylnitrones Serkan Yavuz 1, Hamdi Ozkan 2, Naki Colak 3 and Yilmaz Yildirir 1,* 1 Chemistry Department, Faculty of Science, Gazi University, Ankara 06500, Turkey 2 Chemistry Department, Faculty of Science, ?ank?r? Karatekin University, ?ank?r? 18100, Turkey 3 Chemistry Department, Faculty of Science and Arts, Hitit University, ?orum 19030, Turkey * Author to whom correspondence should be addressed; E-Mail: yildirir@.tr; Tel.: +90-0312-202-11-16; Fax: +90-0312-212-22-79. Received: 20 June 2011; in revised form: 18 July 2011 / Accepted: 19 July 2011 / Published: 8 August 2011 Abstract: A simple, fast, efficient and eco-friendly procedure was developed for the synthesis of alkyl and aryl-N-methylnitrones. The corresponding nitrones of aromatic aldehydes, aliphatic aldehydes and alicyclic carbonyl compounds were prepared from N-methylhydroxylamine hydrochloride and Na2CO3-Na2SO4 by simply grinding at room temperature without using solvent. Keywords: nitrone; grinding; solid-phase synthesis; solventless 1. Introduction Nitrones are important intermediates in synthetic organic chemistry because they give easily 1,3-dipolar cycloaddition reactions with alkenes, alkynes, isocyanates, isothiocyanates, phosphoranes and sulphenes compounds [1]. Especially, the 1,3-dipolar cycloaddition reactions of nitrone-olefin are interesting due to they can create three new contiguous stereogenic centers in a single step [2,3]. Intermolecular and intramolecular nitrone cycloaddition reactions are also useful methods for the formation of biologically active heterocyclic compounds [4-7]. A number of methods have been developed for the synthesis of nitrones. Among these, dehydrogenation of N,N-disubstituted hydroxy