A Facile Synthesis of N-H- and N-Substituted Acridine-1,8-diones under Sonic Condition

Synthesis of an assembly of structurally important N-H- and N-substituted acridine-1,8-diones by CAN (ceric ammonium nitrate) catalysed one-pot four-component reaction of electron-deficient and electron-rich aromatic aldehydes and aromatic amines or ammonium acetate and dimedone or cyclohexyl-1,3-diones at 26°C under sonic condition is reported. The method is clean and energy efficient as it uses a greener method and an eco-friendly catalyst.

[1]  S. Sudha,et al.  Ultrasound assisted synthesis of tetrahydrobenzo[c]xanthene-11-ones using CAN as catalyst. , 2012, Ultrasonics sonochemistry.

[2]  M. A. Pasha,et al.  Glycine catalyzed convenient synthesis of 2-amino-4H-chromenes in aqueous medium under sonic condition. , 2012, Ultrasonics sonochemistry.

[3]  M. A. Pasha,et al.  Cavitational chemistry: a mild and efficient multi-component synthesis of amidoalkyl-2-naphthols using reusable silica chloride as catalyst under sonic conditions. , 2011, Ultrasonics sonochemistry.

[4]  Yuan Gao,et al.  Microwave—prompted Reaction of Cinnamonitrile Derivatives with 5,5—Dimethyl—1,3—cyclohexanedione , 2010 .

[5]  M. Kidwai,et al.  Ceric ammonium nitrate (CAN) catalyzed synthesis of N-substituted decahydroacridine-1,8-diones in PEG , 2010 .

[6]  B. Cheng,et al.  An efficient ultrasound-promoted method for the one-pot synthesis of 7,10,11,12-tetrahydrobenzo[c]acridin-8(9H)-one derivatives. , 2010, Ultrasonics sonochemistry.

[7]  A. Pandit,et al.  Phase transformation of nanostructured titanium dioxide from anatase-to-rutile via combined ultrasound assisted sol-gel technique. , 2010, Ultrasonics sonochemistry.

[8]  Gisela C. Muscia,et al.  Only acridine derivative from Hantzsch-type one-pot three-component reactions , 2009 .

[9]  A. Janowsky,et al.  Discovery of dual function acridones as a new antimalarial chemotype , 2009, Nature.

[10]  M. R. P. Heravi An efficient synthesis of quinolines derivatives promoted by a room temperature ionic liquid at ambient conditions under ultrasound irradiation via the tandem addition/annulation reaction of o-aminoaryl ketones with alpha-methylene ketones. , 2009, Ultrasonics sonochemistry.

[11]  Guolan Dou,et al.  An Efficient Synthesis of Polyhydroacridine Derivatives by the Three-Component Reaction of Aldehydes, Amines and Dimedone in Ionic Liquid. , 2008 .

[12]  O. Fadeyi,et al.  Novel fluorinated acridone derivatives. Part 1: synthesis and evaluation as potential anticancer agents. , 2008, Bioorganic & medicinal chemistry letters.

[13]  Y. K. Rao,et al.  Amberlyst-15: An efficient reusable heterogeneous catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines , 2006 .

[14]  C. Botta,et al.  Electroluminescence from two fluorinated organic emitters embedded in polyvinylcarbazole , 2005 .

[15]  Tong‐Shuang Li,et al.  One-Pot Clean Synthesis of 1,8-Dioxo-decahydroacridines Catalyzed by p-Dodecylbenezenesulfonic Acid in Aqueous Media. , 2005 .

[16]  C. Botta,et al.  Sensitised green emission in an electrically active polymer doped with a fluorinated acridine , 2004 .

[17]  Tong‐Shuang Li,et al.  One-Pot Clean Synthesis of 1,8-Dioxo-decahydroacridines Catalyzed by p-Dodecylbenezenesulfonic Acid in Aqueous Media , 2004 .

[18]  G. Ridolfi,et al.  Synthesis and Properties of Some Derivatives of 1,2,3,4-Tetrafluoroacridine for Solid State Emitting Systems , 2003 .

[19]  F. Charmantray,et al.  Interest of acridine derivatives in the anticancer chemotherapy. , 2001, Current pharmaceutical design.

[20]  E. Davioud‐Charvet,et al.  Antimalarial, antitrypanosomal, and antileishmanial activities and cytotoxicity of bis(9-amino-6-chloro-2-methoxyacridines): influence of the linker. , 2000, Journal of medicinal chemistry.

[21]  Jean-Louis Luche,et al.  Synthetic Organic Sonochemistry , 1998 .

[22]  T. Mason Ultrasound in synthetic organic chemistry , 1998 .

[23]  D. Neckers,et al.  Applicability of decahydroacridine-1,8-dione derivatives as fluorescent probes for monitoring of polymerization processes , 1997 .

[24]  N. Martín,et al.  Synthesis and conformational study of acridine derivatives related to 1,4‐dihydropyridines , 1995 .

[25]  B. Testa,et al.  Screening of unsubstituted cyclic compounds as inhibitors of monoamine oxidases. , 1994, Biochemical pharmacology.