synthesis and structural characterization of 1- and 2-substituted indazoles ester and carboxylic acid derivatives1的合成和结构表征,2-substituted吲唑酯和羧酸衍生物.pdf

Molecules 2006, 11, 867-889 molecules ISSN 1420-3049 Full Paper Synthesis and Structural Characterization of 1- and 2- Substituted Indazoles: Ester and Carboxylic Acid Derivatives Fátima C. Teixeira 1,*, Hélène Ramos 1, Inês F. Antunes 1, M. João M. Curto 1, 2 3 M. Teresa Duarte and Isabel Bento 1 INETI - Departamento de Tecnologia de Indústrias Químicas, Estrada do Paço do Lumiar, 22, 1649- 038 Lisboa, Portugal 2 Instituto Superior Técnico, Centro de Química Estrutural, Complexo I, Av. Rovisco Pais, 1049-001 Lisboa, Portugal 3 Instituto de Tecnologia Química e Biológica, Universidade Nova de Lisboa, Apartado 127, 2781-901 Oeiras, Portugal * Author to whom correspondence should be addressed; E-mail: fatima.teixeira@ineti.pt Received: 4 October 2006; in revised form: 30 October 2006 / Accepted: 13 November 2006 / Published: 14 November 2006 Abstract: A series of indazoles substituted at the N-1 and N-2 positions with ester- containing side chains -(CH ) CO R of different lengths (n = 0-6, 9, 10) are described. 2 n 2 Nucleophilic substitution reactions on halo esters (X(CH ) CO R) by 1H-indazole in 2 n 2 alkaline solution lead to mixtures of N-1 and N-2 isomers, in which the N-1 isomer predominates. Basic hydrolysis of the ester derivatives allowed the synthesis of the corresponding indazole carboxylic acids.