new synthetic approaches to multifunctional phenazinium salt derivatives新的合成方法多功能phenazinium盐衍生物.pdfVIP

Molecules 2003, 8, 505-519 molecules ISSN 1420-3049 Second Eurasian Meeting on Heterocyclic Chemistry “Heterocycles in Organic and Combinatorial Chemistry“ New Synthetic Approaches to Multifunctional Phenazinium Salt Derivatives Inna Yu. Garipova and Vladimir N. Silnikov* Laboratory of Organic Synthesis, Novosibirsk Institute of Bioorganic Chemistry. Lavrentev av., 8, Novosibirsk, 630090, Russia; Tel.: (+7) 3832-333762, Fax: (+7) 3832-333677. *Author to whom correspondence should be addressed; e-mail: silnik@niboch.nsc.ru Received: 13 May 2003; in revised form: / Accepted: 25 June 2003 / Published 30 June 2003 Abstract: Two different approaches are offered for the synthesis under mild conditions of disubstituted phenazinium and benzo[a]phenazinium salts. Direct nucleophilic substitutions by primary and secondary amines in quaternary phenazinium salts containing an additional positive charge in the aliphatic part of the molecule were carried out. The substitution proceeds successively in positions 2 and 7, which allows selective introduction of different substituents into the heterocycle. Direct nucleophilic substitution in quaternary 2-N-alkyl-acetamidophenazinium and 5-alkoxy-benzo[a]phenazinium salts with different amines can also serve as a convenient method for the introduction of two different substituents. Keywords: Phenazinium salts; benzo[a]phenazinium salts; nucleophilic substitutions; amines Introduction Phenazine and phenazine-like molecules have a wide spectrum of biological acti