synthesis of 2,4,6-tri-substituted-1,3,5-triazines合成2,4,6-tri-substituted-1 3 5-triazines.pdfVIP

Molecules 2006, 11, 81-102 molecules ISSN 1420-3049 Synthesis of 2,4,6-Tri-substituted-1,3,5-Triazines Carlos A. M. Afonso 1,*, Nuno M. T. Lourenço 2 and Andreia de A. Rosatella 2 1 CQFM, Departamento de Engenharia Química, Instituto Superior Técnico, 1049-001 Lisboa, Portugal; Fax + 351 21 8464455. 2 REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal. * Author to whom correspondence should be addressed; e-mail: carlosafonso@ist.utl.pt Received: 21 July 2005; in revised form: 8 September 2005 / Accepted: 8 September 2005 / Published: 31 January 2006 Abstract: Several specific synthetic protocols were developed for the preparation from cyanuric chloride of a range of symmetric and non-symmetric di- and tri-substituted 1,3,5-triazines containing alkyl, aromatic, hindered, chiral and achiral hydroxyalkyl, ester and imidazole groups via sequential nucleophilic substitution of the C-Cl bond by C-O, C-N and C-S bonds. Keywords: Cyanuric chloride, s-triazine, 1,3,5-triazine, melamine derivatives. Introduction 1,3,5-Triazines (or s-triazines) are a class of compounds well known for a long time, and still continue the object of considerable interest, mainly due to their applications in different fields, including the production of herbicides and polymer photostabilisers [1]. Some 1,3,5-triazines display important biological properties (Figure 1); for example hexamethylmelamine (HMM, 1) and 2-amino- 4-morphlino-s-triazine (2) are used clinically due to