General Papers ARKIVOC 2009 (xi) 115-122
Synthesis of a bifunctional 1,2,3,4-tetrahydroquinoline derivative: 1,8-bis(9-ethyl-9H-carbazol-3-yl)-1,2,3,4,5,6,7,8-octahydroquino[ 5,6-f]quinoline-3,6-diol
Rimgaile Degutyte, Maryte Daskeviciene, Jolanta Stumbraite, and Vytautas Getautis*
Department of Organic Chemistry, Kaunas University of Technology, Radvilenu pl. 19, LT-50279 Kaunas, Lithuania E-mail:
[email protected]
Abstract
N,N`-Di(3-chloro-2-hydroxypropyl)-N,N`-di(9-ethyl-9H-carbazolyl)-2,7-diaminonaphthalene upon intramolecular cyclization gives 1,8-bis(9-ethyl-9H-carbazol-3-yl)-1,2,3,4,5,6,7,8octahydroquino[ 5,6-f]quinoline-3,6-diol.
Keywords: 1,2,3,4-Tetrahydroquinoline; epichlorohydrin; regioselective cyclization; 1,8-bis(9ethyl- 9H-carbazol-3-yl)-1,2,3,4,5,6,7,8-octahydroquino[5,6-f]quinoline-3,6-diol
Introduction
During recent years rapid developments in the chemistry of 1,2,3,4-tetrahydroquinolines have been observed1. The growing interest in them can be explained by their biological activities. Substituted tetrahydroquinolines are the core structures in many important pharmacological agents2-6, many relatively simple synthetic 1,2,3,4-tetrahydroquinolines are already in use or have been tested as potential drugs.7-9 Besides pharmaceutical applications, tetrahydroquinoline derivatives are useful as pesticides10, antioxidants11, corrosion inhibitors12, and active components of various dyes13. In addition, they also have found application in modern recording technologies.14,15 On the other hand, the carbazole core is present in the structure of some alkaloids16-18, also it is known to be included in semiconductor properties exhibiting compounds which are used in various optoelectronic applications.19,20
Here we targeted our efforts to develop a synthesis method of bifunctional 1,2,3,4tetrahydroquinoline derivative possessing 9-ethylsubstituted carbazolyl radicals that could be a promising synthon for synthesis of new biological or electroactive compounds.
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