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synthesis of substituted phenyl n-(2-hydroxybenzyl)-n-methylcarbamates取代苯的合成n -(2-hydroxybenzyl)-n-methylcarbamates.pdf

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synthesis of substituted phenyl n-(2-hydroxybenzyl)-n-methylcarbamates取代苯的合成n -(2-hydroxybenzyl)-n-methylcarbamates

Molecules 2002, 7, 200ñ205 molecules ISSN 1420-3049 Synthesis of Substituted Phenyl N-(2-hydroxybenzyl)-N-Methyl- carbamates Oldřich HrabÌk, Petr äimůnek*, JaromÌr Mindl, JaromÌr Kav·lek aDepartment of Organic Chemistry, University of Pardubice, Čs. legiÌ 565, 532 10 Pardubice, Czech Republic, Tel. +420 40 603 70 15, Fax +420 40 603 7068. ∗ Author to whom correspondence should by addressed; e-mail: p.simunek@email.cz Received: 29 June 2001; in revised form 29 January 2002 / Accepted: 30 January 2002 / Published: 28 February 2002. Abstract: Thirteen previously unreported substituted phenyl N-(2-hydroxybenzyl)-N- methylcarbamates were prepared by the reaction of substituted 2-hydroxybenzyl-N- methylamines with phenyl chlorocarbonates. They were identified by their 1H- and 13 C-NMR spectra. Keywords: Carbamates syntheses, NMR-spectra Introduction Carbamates are widely used nowadays. Apart from the use of polyurethanes in plastics they are also common components of agrochemicals [ 1] or drugs used for treatment of Alzheimerís disease [2]. Their ability to cyclise to heterocyclic compounds is widely used in organic syntheses [3]. The aim of this work is to synthesise substituted phenyl N-(2-hydroxybenzyl)-N-methylcarbamates 1 which are to be used for studying kinetics and mechanism of their intramolecular cyclization to 3-methyl-4H-1,3- benzoxazin-2(3H)-ones (Scheme 1) Molecules 2002, 7 20 1 Scheme 1 - Preparation of 3-methyl-4H-1,3-benzoxazin-2(3H)-o