Novel Three-Step Synthesis of Imidazo[1,2-c]quinazoline-5(6H)-thione Derivatives

A novel synthesis of Iimidazo[1,2-c]quinazoline-5(6H)-thione framework was developed through a three-step reaction starting from benzil. The resulting (2-nitrophenyl)-4,5-diphenyl-1H-imidazole from the reaction of benzil and different 2-nitrobenzaldehyde, reduction of nitro group and then cyclization reaction with carbon disulfide (CS2). All steps were carried out under easy and user-friendly conditions in short time without using expensive catalysts or reagents.

[1]  Elaheh Salehi,et al.  Phospho Sulfonic Acid Catalyzed Synthesis of Benzimidazole, Benzoxazole and Quinoxaline Derivatives under Green Solvent at Ambient Temperature , 2016 .

[2]  M. Mphahlele,et al.  Novel Polycarbo-Substituted Imidazo[1,2-c]quinazolines: Synthesis and Cytotoxicity Study , 2015, Molecules.

[3]  M. Taghizadeh,et al.  Regioselectivie Synthesis of New Spiro-Oxindolopyrrolidines via a Three-Component Asymmetric 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylides aAnd Chiral Menthyl Cinnamate , 2015 .

[4]  A. Shafiee,et al.  Green Synthesis of New Boron‐Containing Quinazolines: Preparation of Benzo[d][1,3,2]diazaborinin‐4(1H)‐one Derivatives. , 2014 .

[5]  O. Firuzi,et al.  2H-chromene derivatives bearing thiazolidine-2,4-dione, rhodanine or hydantoin moieties as potential anticancer agents. , 2013, European journal of medicinal chemistry.

[6]  A. Shafiee,et al.  One‐Pot, Four‐Component Synthesis of Novel Imidazo[2,1‐b]thiazol‐5‐amine Derivatives. , 2013 .

[7]  A. Shafiee,et al.  Synthesis of Novel 1,4‐Benzodiazepine‐3,5‐dione Derivatives: Reaction of 2‐Aminobenzamides under Bargellini Reaction Conditions. , 2013 .

[8]  Yanhui Shi,et al.  An efficient synthesis of 3-benzylquinazolin-4(1H)-one derivatives under catalyst-free and solvent-free conditions , 2012 .

[9]  C. Hertweck,et al.  Farinamycin, a quinazoline from Streptomyces griseus. , 2011, Journal of natural products.

[10]  Xingzhong Liu,et al.  N-hydroxypyridones, phenylhydrazones, and a quinazolinone from Isaria farinosa. , 2011, Journal of natural products.

[11]  M. Al-Omar,et al.  Design, synthesis and biological evaluation of novel quinazoline derivatives as potential antitumor agents: molecular docking study. , 2010, European journal of medicinal chemistry.

[12]  P. Langer,et al.  Synthesis of 5-Thioxo-6H-imidazo[1,2-c]quinazolines and Related Compounds Based on Cyclocondensations of 2-Isothiocyanatobenzonitrile (ITCB) with α-Aminoketones. , 2008 .

[13]  Michael Decker,et al.  Novel inhibitors of acetyl- and butyrylcholinesterase derived from the alkaloids dehydroevodiamine and rutaecarpine. , 2005, European journal of medicinal chemistry.

[14]  J. Bergman,et al.  Recent Developments in the Field of Quinazoline Chemistry , 2003 .

[15]  R. Bahekar,et al.  Synthesis, evaluation and structure-activity relationships of 5-alkyl-2,3-dihydroimidazo[1,2-c] quinazoline, 2,3-dihydroimidazo[1,2-c]quinazolin-5(6H)-thiones and their oxo-analogues as new potential bronchodilators. , 2011, Arzneimittel-Forschung.

[16]  H. Cottam,et al.  Substituted isoquinolines and quinazolines as potential antiinflammatory agents. Synthesis and biological evaluation of inhibitors of tumor necrosis factor alpha. , 1999, Journal of medicinal chemistry.

[17]  A. Kamal,et al.  Enzymatic cyclizations mediated by ultrasonically stimulated baker's yeast: synthesis of imidazo-fused heterocycles , 1990 .

[18]  R. A. Kulp,et al.  New sedative and hypotensive 3-substituted 2,4(1H,3H)-quinazolinediones. , 1965, Journal of medicinal chemistry.

[19]  H. Sachdev,et al.  Thiopegan derivatives—XXII , 1961 .

[20]  D. G. Wenzel.  Anticonvulsant activity of some uracils and related compounds. , 1955, Journal of the American Pharmaceutical Association. American Pharmaceutical Association.

[21]  E. Wagner,et al.  ISATOIC ANHYDRIDE. I. REACTIONS WITH PRIMARY AND SECONDARY AMINES AND WITH SOME AMIDES1 , 1944 .