Reactivity of 4-tert-Butyldimethylsiloxy-1,2,3,6-tetrahydropyridines with Hydrazines 英文参考文献.docVIP

Molecules 2006, 11, 929-939 molecules ISSN 1420-3049 Full Paper Reactivity of 4-tert-Butyldimethylsiloxy-1,2,3,6-tetrahydro- pyridines with Hydrazines Javier Figueroa, Esther Caballero*, Pilar Puebla, Fernando Tomé and Manuel Medarde Laboratorio de Química Orgánica y Farmacéutica, Facultad de Farmacia, Campus Miguel de Unamuno, 37007 Salamanca, Spain *Author to whom correspondence should be addressed; e-mail: escab@usal.es Received: 2 November 2006; in revised form: 29 November 2006 / Accepted: 29 November 2006 / Published: 30 November 2006 Abstract: The reactivity of 6-(nitrophenyl or trimethoxyphenyl)-4-tert-butyldimethyl- siloxy-1,2,3,6-tetrahydropyridine derivatives with hydrazines under acid conditions is described. The structure of the products isolated ? hydrazones, pyrazolines or pyridazinones ? depended on the conditions used. In addition, a systematic study of the reaction outcomes was carried out by introducing variations on the substituents of the tetrahydropyridine ring. Keywords: Siloxy-1,2,3,6-tetrahydropyridines, hydrazones, pyrazolines, pyridazinones. Introduction The Fischer reaction of piperidones with phenylhydrazines has been described for the preparation of compounds with the carboline structure. The (α, β or γ) carboline derivatives represent a large number of naturally and synthetic indole alkaloids with interesting biological and pharmaceutical activities [1]. β-Carboline-type alkaloids are the best known, owing to their antiviral, antitumor and antimicrobial activities [2, 3]. γ-Carbolines have also shown antipsychotic, antibiotic or antitumor activities [4, 5]. This Fischer reaction has been described to give the carbolines in good to moderate yields under a variety of acidic conditions. For instance, the reaction between N-methyl-4-piperidone and tolylhydrazine in glacial acetic acid gives the corresponding carboline in 60% yield; if the react