Ammonium Oxalate as an Efficient Catalyst for One-Pot Synthesis of Tetrahydrobenzo [a]xanthen-11-one Derivatives Under Solvent-Free Conditions

A simple and efficient procedure for the synthesis of 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives has been developed via one-pot three-component reaction of 2-naphthol, aldehydes, and dimedone in the presence of ammonium oxalate as a mild and inexpensive catalyst under solvent-free conditions. The present method is operationally simple and offers several advantages such as high yields, short reaction time, economic availability of the catalyst, and simple workup.

[1]  N. Foroughifar,et al.  Ammonium Chloride–Catalyzed One-Pot Synthesis of Tetrahydrobenzo[α]xanthen-11-one Derivatives Under Solvent-Free Conditions , 2011 .

[2]  N. Foroughifar,et al.  A Straightforward and Efficient Catalyst‐Free One‐Pot Synthesis of N‐Acyl‐1,3‐diaryl‐2‐azaphenalene Derivatives via Multicomponent Reactions. , 2010 .

[3]  Atul Kumar,et al.  Diversity oriented synthesis of benzoxanthene and benzochromene libraries via one-pot, three-component reactions and their anti-proliferative activity. , 2010, Journal of combinatorial chemistry.

[4]  M. Heravi,et al.  Sulfamic acid catalyzed solvent-free synthesis of 10-aryl-7,7-dimethyl-6,7,8,10-tetrahydro-9H-[1,3]-dioxolo [4,5- b]xanthen-9-ones and 12-aryl-9,9-dimethyl-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-ones , 2010, Molecular Diversity.

[5]  N. Foroughifar,et al.  Simple and Efficient Method for Synthesis of Novel 4-Substituted 1-Acylthiosemicarbazides via One-Pot Multicomponent Reactions , 2009 .

[6]  G. Nandi,et al.  An efficient one-pot synthesis of tetrahydrobenzo[a]xanthene-11-one and diazabenzo[a]anthracene-9,11-dione derivatives under solvent free condition , 2009 .

[7]  N. Foroughifar,et al.  A Catalytic and Green Procedure for Synthesis of 12-Aryl- or 12-Alkyl-8,9,10,12-Tetrahydrobenzo[α]xanthen-11-one Derivatives under Solvent-Free Conditions , 2009 .

[8]  J. Khurana,et al.  pTSA-catalyzed one-pot synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones in ionic liquid and neat conditions , 2009 .

[9]  Hong-juan Wang,et al.  Synthesis 12-Aryl or 12-Alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives catalyzed by dodecatungstophosphoric acid , 2009 .

[10]  W. Su,et al.  Strontium triflate catalyzed one-pot condensation of β-naphthol, aldehydes and cyclic 1,3-dicarbonyl compounds , 2008 .

[11]  M. Krishnaiah,et al.  An Efficient and Convenient Protocol for the Synthesis of Novel 12-Aryl- or 12-Alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one Derivatives , 2007 .

[12]  B. Bhowmik,et al.  Photophysics of xanthene dyes in surfactant solution. , 2005, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[13]  A. Jha,et al.  Convenient Synthesis of 12H‐Benzo[a]xanthenes from 2‐Tetralone. , 2005 .

[14]  A. Jha,et al.  Convenient synthesis of 12H-benzo[a]xanthenes from 2-tetralone , 2004 .

[15]  A. El-Brashy,et al.  Spectrophotometric determination of some fluoroquinolone antibacterials by binary complex formation with xanthene dyes. , 2004, Farmaco.

[16]  A. Fairlamb,et al.  Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents , 2003 .

[17]  Jim-Min Fang,et al.  SYNTHESIS OF XANTHENES, INDANES, AND TETRAHYDRONAPHTHALENES VIA INTRAMOLECULAR PHENYL–CARBONYL COUPLING REACTIONS , 2001 .

[18]  D. Knight,et al.  The First High-yielding Benzyne Cyclisation Using a Phenolic Nucleophile: A New Route to Xanthenes , 1998 .

[19]  R. Ion,et al.  The incorporation of various porphyrins into blood cells measured via flow cytometry, absorption and emission spectroscopy. , 1998, Acta biochimica Polonica.

[20]  C. Tsai,et al.  Potentiation of the antiviral activity of poly r(A-U) by xanthene dyes. , 1990, Cell biology international reports.

[21]  D. D. Giannini,et al.  Dibenzoxanthene derivatives and related products from .beta.-naphthol and aldehydes or acetals , 1982 .

[22]  N. Sarkar,et al.  THE CONDENSATION OF PRIMARY ALCOHOLS WITH RESORCINOL AND OTHER HYDROXY AROMATIC COMPOUNDS , 1925 .