Solvent free, Ni-nanoparticle catalyzed greener synthesis and photophysical studies of novel 2H-indazolo[2,1-b] phthalazine-trione derivatives

A nickel nanoparticle (NPs) catalyzed one-pot three component reaction of phthalhydrazide, dimedone and aryl aldehydes under solvent free conditions has been reported. The present approach offers the advantages of simple methodology, clean and mild reaction conditions, short reaction time, low environmental impact, high yield, and excellent purity. The synthesized compounds (2H-indazolo[2,1-b] phthalazine-trione) are found to be suitable candidates for efficient fluorogenic assays to monitor bio-chemical environments.

[1]  A. Zare,et al.  Solvent-free, one-pot, four-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones using sulfuric acid-modified PEG-6000 as a green recyclable and biodegradable polymeric catalyst , 2012 .

[2]  S. Mitra,et al.  Fluorescence behavior of ethidium bromide in homogeneous solvents and in presence of bile acid hosts , 2012 .

[3]  Y. Jeong,et al.  Microwave-assisted, montmorillonite K-10 catalyzed three-component synthesis of 2H-indazolo(2,1-b)phthalazine-triones under solvent-free conditions , 2012 .

[4]  M. Saha,et al.  Pd(0) NPs: a novel and reusable catalyst for the synthesis of bis(heterocyclyl)methanes in water , 2012 .

[5]  N. Mishra,et al.  Dodecylphosphonic acid (DPA): a highly efficient catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions , 2012 .

[6]  Kidwai Mazaahir,et al.  Efficient CAN catalyzed synthesis of 1H-indazolo[1,2-b] phthalazine-1,6,11-triones: An eco-friendly protocol , 2012 .

[7]  A. Hasaninejad,et al.  Ultrasound-promoted catalyst-free one-pot four component synthesis of 2H-indazolo[2,1-b]phthalazine-triones in neutral ionic liquid 1-butyl-3-methylimidazolium bromide. , 2012, Ultrasonics sonochemistry.

[8]  R. K. Verma,et al.  Solvent-free sonochemical one-pot three-component synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11-triones and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones , 2011 .

[9]  D. Raghuvanshi,et al.  A highly efficient green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives and their photophysical studies , 2011 .

[10]  M. Saha,et al.  Facile Microwave-Promoted Knoevenagel Condensation and the Combination of Knoevenagel/ Michael addition Reaction in Aqueous Medium Containing Ionic Surfactant , 2011 .

[11]  M. Saha,et al.  Palladium(0) nanoparticles: an efficient catalyst for the one-pot synthesis of polyhydroquinolines , 2011 .

[12]  M. Ghavidel,et al.  One-pot synthesis of aliphatic and aromatic 2H-indazolo[2,1-b]phthalazine-triones catalyzed by N-halosulfonamides under solvent-free conditions , 2011 .

[13]  A. Hassankhani,et al.  A rapid, one-pot, four-component route to 2H-indazolo[2,1-b]-phthalazine-triones , 2011 .

[14]  A. Coyne,et al.  Water: nature's reaction enforcer--comparative effects for organic synthesis "in-water" and "on-water". , 2010, Chemical reviews.

[15]  J. Yadav,et al.  Phosphomolybdic Acid (PMA) - SiO2 as a Heterogeneous Solid Acid Catalyst for the One-Pot Synthesis of 2H-Indazolo[1,2-b]phthalazine-triones , 2010 .

[16]  R. Fazaeli,et al.  Heteropoly Acid in Ionic Liquid - An Efficient Catalyst for the Preparation of 2H-Indazolo(2,1-b)Phthalazine-Triones , 2010 .

[17]  J. Khurana,et al.  Efficient one-pot syntheses of 2H-indazolo[2,1-b] phthalazine-triones by catalytic H2SO4 in water–ethanol or ionic liquid , 2009 .

[18]  Rajashaker Bantu,et al.  TMSCl‐mediated one‐pot, three‐component synthesis of 2H‐indazolo[2,1‐b]phthalazine‐triones , 2009 .

[19]  H. Shaterian,et al.  Silica sulfuric acid as an efficient catalyst for the preparation of 2H-indazolo[2,1-b]phthalazine-triones , 2008 .

[20]  H. Khavasi,et al.  One-pot, three-component route to 2H-indazolo[2,1-b]phthalazine-triones , 2008 .

[21]  Ajeet Kumar,et al.  Ni-nanoparticles: An efficient green catalyst for chemo-selective oxidative coupling of thiols , 2007 .

[22]  C. Ryu,et al.  Synthesis and antifungal activity of 6-arylamino-phthalazine-5,8-diones and 6,7-bis(arylthio)-phthalazine-5,8-diones. , 2007, Bioorganic & medicinal chemistry letters.

[23]  P. Gong,et al.  Synthesis and anticancer activities of novel 1,4-disubstituted phthalazines. , 2006, Molecules.

[24]  M. El-Sayed,et al.  Chemistry and properties of nanocrystals of different shapes. , 2005, Chemical reviews.

[25]  J. Vederas,et al.  Structural variations in keto-glutamines for improved inhibition against hepatitis A virus 3C proteinase. , 2004, Bioorganic & medicinal chemistry letters.

[26]  K. Pihlaja,et al.  1H and 13C NMR Study of 1-Hydrazino-2,3-dihydro-1H-pyrazolo[1,2-a]pyridazine-5,8-diones and -1H-pyrazolo[1,2-b]phthalazine-5,10-diones and Their Ring-Chain Tautomerism , 2002 .

[27]  M. Baraldi,et al.  Synthesis and anticonvulsant activity of novel and potent 6,7-methylenedioxyphthalazin-1(2H)-ones. , 2000, Journal of medicinal chemistry.

[28]  Szu-Han Wu,et al.  Synthesis of Nickel Nanoparticles in Water-in-Oil Microemulsions , 2000 .

[29]  K. Miyazaki,et al.  4-Benzylamino-1-chloro-6-substituted phthalazines: synthesis and inhibitory activity toward phosphodiesterase 5. , 1998, Journal of medicinal chemistry.

[30]  K. Kubo,et al.  Studies on cardiotonic agents. II. Synthesis of novel phthalazine and 1,2,3-benzotriazine derivatives. , 1990, Chemical & pharmaceutical bulletin.

[31]  David Phillips,et al.  Photophysics of some common fluorescence standards , 1983 .

[32]  P. R. Bevington,et al.  Data Reduction and Error Analysis for the Physical Sciences , 1969 .