Zinc Chloride Catalyzed Collective Synthesis of Arylmethylene Bis(3- hydroxy-2-cyclohexene-1-ones) and 1,8-Dioxo-octahydroxanthene/acridine Derivatives

ISSN: 1875-6255 (Online)
ISSN: 1570-1786 (Print)


Volume 11, 10 Issues, 2014


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Letters in Organic Chemistry

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Zinc Chloride Catalyzed Collective Synthesis of Arylmethylene Bis(3- hydroxy-2-cyclohexene-1-ones) and 1,8-Dioxo-octahydroxanthene/acridine Derivatives

Author(s): Subramaniapillai Selva Ganesan, Jagatheeswaran Kothandapani and Asaithampi Ganesan

Affiliation: School of Chemical and Biotechnology, SASTRA University, Thanjavur-613401, Tamil Nadu, India

Abstract

Catalytic amount of ZnCl2 efficiently promoted rapid synthesis of arylmethylene bis(3-hydroxy-2-cyclohexene- 1-one) in water at room temperature in excellent yield. At elevated temperature, ZnCl2 also catalyzed one-pot synthesis of 1,8-dioxo-octahydroxanthene and 1,8-dioxo-decahydroacridine derivatives in good yield. In specific instances, unusual dissociation of dimedone from the arylmethylene bis(3-hydroxy-2-cyclohexene-1-one) was identified in the reaction medium. It was minimized/avoided by the addition of known excess dimedone to the reaction mixture in the one-pot synthesis of 1,8-dioxo-octahydroxanthene




Keywords: Acridine, green synthesis, one-pot synthesis, xanthene, zinc chloride.

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Article Details

Volume: 11
Issue Number: 9
First Page: 682
Last Page: 687
Page Count: 6
DOI: 10.2174/1570178611666140612211155
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