An Efficient One-Pot Synthesis of 2,3-dihydroquinazolin-4(1H)-ones in Green Media

A series of mono- and disubstituted 2,3-dihydroquinazoline-4(1H)-ones have been synthesized in good yields by one-pot reaction using isatoic anhydride, ammonium acetate or amines and aldehydes in green and mild reaction conditions. The effects of various parameters such as the solvent, catalyst amount, reaction time, and temperature were examined. The protocol is simple, efficient, and environmentally benign and the catalyst can be recovered and reused without evident loss of reactivity.

[1]  S. Ganguly,et al.  Synthesis, antiviral and cytotoxic investigation of 2-phenyl-3-substituted quinazolin-4(3H)-ones. , 2011, European review for medical and pharmacological sciences.

[2]  C. Cai,et al.  Iodine: Selectively Promote the Synthesis of Mono Substituted Quinazolin-4(3H)-ones and 2,3-Dihydroquinazolin-4(1H)-ones in One-Pot , 2010 .

[3]  N. Foroughifar,et al.  Efficient One-Pot Synthesis of Polyhydroquinoline Derivatives Using Silica Sulfuric Acid as a Heterogeneous and Reusable Catalyst Under Conventional Heating and Energy-Saving Microwave Irradiation , 2009 .

[4]  N. Foroughifar,et al.  Synthesis of a new class of azathia crown macrocycles containing two 1,2,4-triazole or two 1,3,4-thiadiazole rings as subunits , 2009 .

[5]  Hanan H. Georgey,et al.  Synthesis and Anticonvulsant Activity of Some Quinazolin-4-(3H)-one Derivatives , 2008, Molecules.

[6]  N. Lingaiah,et al.  Tetrabutylammonium bromide (TBAB) in isopropanol: An efficient, novel, neutral and recyclable catalytic system for the synthesis of 2,4,5-trisubstituted imidazoles , 2008 .

[7]  W. Su,et al.  Gallium(III) triflate-catalyzed one-pot selective synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones , 2008 .

[8]  N. Foroughifar,et al.  A Novel Efficient Four-and Five-Component, One-Pot Synthesis of 4-Semicarbazonoalkyl-2-Naphthols , 2008 .

[9]  N. Lingaiah,et al.  Catalysis by an ionic liquid: Highly efficient solvent-free synthesis of aryl-14H-dibenzo[a.j]xanthenes by molten tetrabutylammonium bromide under conventional and microwave heating , 2008 .

[10]  W. Su,et al.  Eco-friendly synthesis of 2,3 -dihydroquinazolin -4 (1H) -ones in ionic liquids or ionic liquid-water without additional catalyst , 2007 .

[11]  Christopher Hardacre,et al.  Catalysis in ionic liquids. , 2007, Chemical reviews.

[12]  S. Mallakpour,et al.  Tetrabutylammonium bromide: An efficient, green and novel media for polycondensation of 4-(4-dimethylaminophenyl)-1,2,4-triazolidine-3,5-dione with diisocyanates , 2007 .

[13]  H. Hailes Reaction solvent selection : The potential of water as a solvent for organic transformations , 2007 .

[14]  M. Dabiri,et al.  One‐Pot, Three‐Component Synthesis of 2,3‐Dihydro‐4(1H)‐quinazolinones by Montmorillonite K‐10 as an Efficient and Reusable Catalyst , 2006 .

[15]  M. Dabiri,et al.  Water‐Accelerated Synthesis of Novel Bis‐2,3‐dihydroquinazolin‐4‐(1H)‐one Derivatives. , 2006 .

[16]  M. Dabiri,et al.  Efficient Synthesis of Mono‐ and Disubstituted 2,3‐Dihydroquinazolin‐4(1H)‐ones Using KAl(SO4)2×12H2O as a Reusable Catalyst in Water and Ethanol. , 2005 .

[17]  J. Fettinger,et al.  Stannous chloride in alcohol: a one-pot conversion of 2-nitro-N-arylbenzamides to 2,3-dihydro-1H-quinazoline-4-ones. , 2005, The Journal of organic chemistry.

[18]  R. Sheldon Green solvents for sustainable organic synthesis: state of the art , 2005 .

[19]  M. Zolfigol,et al.  A Novel Method for the One-Pot Three-Component Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones , 2005 .

[20]  D. Shi,et al.  An efficient synthesis of quinazoline derivatives with the aid of low‐valent titanium reagent , 2005 .

[21]  Sushma Chauhan,et al.  Chemical and biochemical transformations in ionic liquids , 2005 .

[22]  A. Khosropour,et al.  A powerful, practical and chemoselective synthesis of 2-anilinoalkanols catalyzed by Bi(TFA)3 or Bi(OTf)3 in the presence of molten TBAB , 2004 .

[23]  G. Kukreja,et al.  Nickel Boride Mediated Reductive Desulfurization of 2-Thioxo-4(3H)-quinazolinones: A New Synthesis of Quinazolin-4(3H)-ones and 2,3-Dihydro-4(1H)-quinazolinones. , 2004 .

[24]  G. Kukreja,et al.  Nickel boride mediated reductive desulfurization of 2‐thioxo‐4(3H)‐quinazolinones: A new synthesis of quinazolin‐4(3H)‐ones and 2,3‐dihydro‐4(1H)‐quinazolinones , 2003 .

[25]  W. Su,et al.  Reductive Cyclization of Nitro and Azide Compounds with Aldehydes and Ketones Promoted by Metallic Samarium and Catalytic Amount of Iodine. , 2003 .

[26]  D. Shi,et al.  Synthesis of quinazolin-4(3H)-ones and 1,2-dihydroquinazolin-4(3H)-ones with the aid of a low-valent titanium reagent , 2003 .

[27]  B. Ranu,et al.  An efficient synthesis of pyrroles by a one-pot, three-component condensation of a carbonyl compound, an amine and a nitroalkene in a molten ammonium salt , 2003 .

[28]  M. Zolfigol,et al.  Silica sulfuric acid: an efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones , 2003 .

[29]  B. Ranu,et al.  Catalysis by an ionic liquid: efficient conjugate addition of thiols to electron deficient alkenes catalyzed by molten tetrabutylammonium bromide under solvent-free conditions , 2003 .

[30]  W. Su,et al.  Reductive Cyclization of Nitro and Azide Compounds with Aldehydes and Ketones Promoted by Metallic Samarium and Catalytic Amount of Iodine , 2002 .

[31]  L. Vaccaro,et al.  Efficient O-trimethylsilylation of alcohols and phenols with trimethylsilyl azide catalyzed by tetrabutylammonium bromide under neat conditions. , 2001, The Journal of organic chemistry.

[32]  S. Kuo,et al.  Antitumor agents. Part 204: synthesis and biological evaluation of substituted 2-aryl quinazolinones. , 2001, Bioorganic & medicinal chemistry letters.

[33]  S. Kuo,et al.  6-Alkylamino- and 2,3-dihydro-3'-methoxy-2-phenyl-4-quinazolinones and related compounds: their synthesis, cytotoxicity, and inhibition of tubulin polymerization. , 2000, Journal of medicinal chemistry.

[34]  N. Urdaneta,et al.  The Synthesis of Substituted 2-Aryl 4(3H)-Quinazolinones Using NaHSO3/DMA. Steric Effect upon the Cyclization-Dehydrogenation Step. , 2000 .

[35]  N. Urdaneta,et al.  The Synthesis of Substituted 2-Aryl 4(3H)-Quinazolinones using Nahso3/Dma. Steric Effect upon the Cyclisation-Dehydrogenation Step , 2000 .

[36]  K. Tanaka,et al.  Solvent-free organic synthesis. , 2000, Chemical reviews.

[37]  B. Roth,et al.  Novel nonpeptide CCK-B antagonists: design and development of quinazolinone derivatives as potent, selective, and orally active CCK-B antagonists. , 1998, Journal of medicinal chemistry.

[38]  G. J. Sutherland,et al.  Reactions of anthranilamide and o-aminoacetophenone with benzil and benzoin , 1969 .