10 - Iranian Journal of Organic Chemistry 2 (2009) 118-126...

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Iranian Journal of Organic Chemistry 2 (2009) 118-126 118 Solvent-free synthesis of 14-aryl(alkyl)-14 H -dibenzo[ a,j ]xanthene, 9-aryl(alkyl)- 3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2 H -xanthene-1,8-dione and 2-Amino- 5,6,7,8-tetrahydro-5-oxo-4-aryl-7,7-dimethyl-4 H -benzo-[ b ]-pyran derivatives using InCl 3 as catalyst Hamid Reza Tavakoli, a Hassan Zamani, a,b* Mohammad Hassan Ghorbani, a Hossein Etedali Habibabadi a a Department of Biochemistry, Islamic Azad University,Falavarjan branch, Isfahan, Iran b Faculty of Science, University of Applied Science and Technology, Iran Abstract: An efficient synthesis route to dibenzoxanthene, xanthene and benzopyran derivatives from reaction of divergent aldehydes with β -naphthol, dimedone and ethyl cyanoacetate respectively under solvent-free conditions by indium chloride as a relative inexpensive, eco-friendly, easy available, non-volatile, non-explosion, thermally robust, recyclable and easy to handle catalyst at 90°C with good to excellent yields is described. Unenhanced reaction times, simple reaction protocol and work-up, improved synthesis of these materials in the presence of this heterogeneous catalyst. Keywords: Dibenzoxanthene; Xanthene, Benzopyran; Solvent-free; Indium chloride Introduction Xanthenes and benzoxanthenes have received much attention because of their wide range of therapeutic and biological properties, such as antibacterial [1], antiviral [2], and anti-inflammatory activities [3]. These compounds have emerged as sensitizers in photodynamic therapy [4,5], and are used as leuco-dyes [6] and in laser technology [7]. Furthermore, benzoxanthenes are used as dyes [6,8], in laser technologies [9] and in fluorescent materials [10]. they are also utilized as antagonists for paralyzing action of zoxazolamine [11,12]. Thus, the synthesis of benzoxanthene derivatives currently is of great interest. 4 H -Benzo[ b ]pyrans are an important class of compounds which have received considerable attention in recent years due to their wide range of biological activities [13]. Compounds with these ring systems have diverse pharmacological activities such as anti- coagulant, anticancer, spasmolytic, diuretic, anti- ancaphylactia [14] and served as important regulators for potassium cation channel [15]. 4 H -Pyrans also constitute the structural unit of a series of natural products [16]. A number of 2-amino-4 H -pyrans are useful as photoactive materials [17]. Dibenzoxanthenes *Corresponding author. Fax: +(98) 3116270708; Tel: +(98) 3116240383 E-mail: zamani.hassan@gmail.com has been prepared by different methods. However, many of these methods suffer from certain drawbacks including longer reaction times, unsatisfactory yields, harsh reaction conditions and necessity of excess of reagents and catalysts. One of the best methods is the reaction of
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10 - Iranian Journal of Organic Chemistry 2 (2009) 118-126...

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