Fast Solvent-free Alkylation of Amides and Lactams under Microwave Irradiation.docVIP

Molecules 1999, 4, 333-337 molecules ISSN 1420-3049 Fast Solvent-free Alkylation of Amides and Lactams under Microwave Irradiation Dariusz Bogdal Department of Chemistry, Politechnika Krakowska, ul. Warszawska 24, 31-155 Krakow, Poland Tel.: +48 12 634-24-25; Fax: +48 12 634-24-25; E-mail: pcbogdal@.pl Received: 11 October 1999 / Accepted: 20 October 1999 / Published: 25 November 1999 Abstract: N-Substituted amides and lactams are rapidly N-alkylated under solvent-free phase-transfer catalytic conditions using microwaves. Keywords: amides, lactams, N-alkylation, solvent-free, microwave. Introduction The N-alkylation of amides to N,N-disubstituted amides is an important transformation in organic synthesis because disubstituted amides are valuable material for the synthesis of tertiary amines [1]. On the other hand, amides are very weak bases so they must first be converted to their conjugate bases in order to be alkylated [2]. For instance, the preparation of N-substituted and N,N-disubstituted amides can be performed with their sodium salts and alkyl bromides or iodides [3]. In the past, three methods were applied to convert amides into their alkali salts and further preparation of substituted amides. In the first method, an amide and sodium were dispersed in an inert solvent followed by addition of an alkyl halide [4]. In the second, a mixture of amide, potassium hydroxide, and alkyl halide was reacted in an ethanolic solution [5], whereas third method utilised sodium hydride to form the sodium salt of an amide followed by addition of an alkyl halide [6]. All of them suffered from prolonged reaction time under rather drastic conditions. Later, it have been found that amides could be turned into their salts and directly alkylated without the preliminary step of salt formation under phase-transfer catalytic (PTC) conditions [7]. ? 1999 by MDPI (). Reproduction is permitted for noncommercial purposes.