Solvent-mediated Highly Efficient Synthesis of [1,2,4]triazolo/benzimidazoloquinazolinone Derivatives.

OBJECTIVE An efficient and catalyst-free procedure for the synthesis of [1,2,4]triazolo/benzimidazolo quinazolinones has been developed in 2,2,2-trifluoroethanol or deep eutectic solvent(DESs) as a clean reaction media. METHODS All of the obtained products are known compounds and identified by IR, 1HNMR,13CNMR, and melting points. RESULT Various products were obtained in good to excellent yields under reaction conditions. CONCLUSION We have efficiently developed a practical and catalyst-free approach for the synthesis of [1,2,4]triazolo/benzimidazolo quinazolinones employing TFE as a clean and reusable media.

[1]  P. Shanmugam,et al.  Phosphotungstic acid mediated, microwave assisted solvent-free green synthesis of highly functionalized 2ˈ-spiro and 2, 3-dihydro quinazolinone and 2-methylamino benzamide derivatives from aryl and heteroaryl 2-amino amides , 2019, Tetrahedron Letters.

[2]  B. Crousse,et al.  Friedel–Crafts alkylation reaction with fluorinated alcohols as hydrogen-bond donors and solvents , 2018, RSC Advances.

[3]  M. Heravi,et al.  H4[W12SiO40] grafted on magnetic chitosan: a green nanocatalyst for the synthesis of [1,2,4]triazolo/benzimidazolo quinazolinone derivatives , 2017 .

[4]  F. Shirini,et al.  A simple and convenient synthesis of [1,2,4]triazolo/benzimidazolo ‎quinazolinone and [1,2,4]triazolo[1,5-a]pyrimidine derivatives catalyzed by ‎DABCO-based ionic liquids , 2017, Journal of the Iranian Chemical Society.

[5]  Luís C. Branco,et al.  Deep eutectic solvents (DESs) as low-cost and green electrolytes for electrochromic devices , 2017 .

[6]  Santosh S. Undare,et al.  An efficient, one-pot three components synthesis of [1,2,4] triazoloquinazolinone derivatives using anthranilic acid as green catalyst , 2017, Research on Chemical Intermediates.

[7]  P. Mahulikar,et al.  Facile DES-mediated synthesis and antioxidant potency of benzimidazoquinazolinone motifs , 2017, Research on Chemical Intermediates.

[8]  Zhaojia Hang,et al.  Free-Radical Triggered Ordered Domino Reaction: An Approach to C-C Bond Formation via Selective Functionalization of α-Hydroxyl-(sp(3))C-H in Fluorinated Alcohols. , 2016, Organic letters.

[9]  A. Karimi,et al.  Mild Synthesis of mono-, bis- and tris 1,2-Dihydrobenzo[4,5]imidazo[1,2- a]pyrimidine Derivatives Using Alkyl Disulfamic Acid Functionalized Magnetic Nanoparticles , 2016 .

[10]  R. Nagarajan,et al.  Deep eutectic solvent mediated synthesis of quinazolinones and dihydroquinazolinones: synthesis of natural products and drugs , 2016 .

[11]  Chung‐Ming Sun,et al.  A Novel Mechanistic Study on Ultrasound-Assisted, One-Pot Synthesis of Functionalized Benzimidazo[2,1-b]quinazolin-1(1H)-ones. , 2016, ACS combinatorial science.

[12]  U. A. Kshirsagar,et al.  Recent developments in the chemistry of quinazolinone alkaloids. , 2015, Organic & biomolecular chemistry.

[13]  M. Hashim,et al.  Potential applications of deep eutectic solvents in nanotechnology: Part II , 2015, Chemical Engineering Journal.

[14]  Hongyu Cao,et al.  Deep eutectic solvent catalyzed Friedel–Crafts alkylation of electron-rich arenes with aldehydes , 2015 .

[15]  P. Liu,et al.  Recent advances in the application of deep eutectic solvents as sustainable media as well as catalysts in organic reactions , 2015 .

[16]  Samad Khaksar.  Fluorinated alcohols: A magic medium for the synthesis of heterocyclic compounds , 2015 .

[17]  M. Maghsoodlou,et al.  Nano-SiO2: a green, efficient, and reusable heterogeneous catalyst for the synthesis of quinazolinone derivatives , 2015, Journal of the Iranian Chemical Society.

[18]  M. Maghsoodlou,et al.  Catalytic systems containing p-toluenesulfonic acid monohydrate catalyzed the synthesis of triazoloquinazolinone and benzimidazoquinazolinone derivatives , 2014, Monatshefte für Chemie - Chemical Monthly.

[19]  M. Gutiérrez,et al.  Deep eutectic solvents in polymerizations: a greener alternative to conventional syntheses. , 2014, ChemSusChem.

[20]  K. Nagaiah,et al.  A simple, convenient one-pot synthesis of [1,2,4]triazolo/benzimidazolo quinazolinone derivatives by using molecular iodine , 2013 .

[21]  S. Belwal.  Green Revolution in Chemistry by Microwave Assisted Synthesis: A Review , 2013 .

[22]  Burkhard König,et al.  Low melting mixtures in organic synthesis – an alternative to ionic liquids? , 2012 .

[23]  Samad Khaksar,et al.  A facile and efficient synthesis of 2-amino-3-cyano-4H-chromenes and tetrahydrobenzo[b]pyrans using 2,2,2-trifluoroethanol as a metal-free and reusable medium , 2012 .

[24]  Samad Khaksar,et al.  A Novel One-Pot Synthesis of Quinoxaline Derivatives in Fluorinated Alcohols , 2012 .

[25]  G. Baker,et al.  Protease activation in glycerol-based deep eutectic solvents. , 2011, Journal of molecular catalysis. B, Enzymatic.

[26]  A. Heydari,et al.  Lewis acid catalyst free synthesis of benzimidazoles and formamidines in 1,1,1,3,3,3-hexafluoro-2-propanol , 2010 .

[27]  J. Qu,et al.  Friedel-Crafts alkylation of arenes with epoxides promoted by fluorinated alcohols or water. , 2010, Chemical communications.

[28]  M. Heravi,et al.  Sulfamic Acid–Catalyzed, Three-Component, One-Pot Synthesis of [1,2,4]Triazolo/Benzimidazolo Quinazolinone Derivatives , 2010 .

[29]  A. Heydari,et al.  One-step, synthesis of Hantzsch esters and polyhydroquinoline derivatives in fluoro alcohols , 2009 .

[30]  A. Heydari,et al.  Trifluoroethanol as a metal-free, homogeneous and recyclable medium for the efficient one-pot synthesis of α-amino nitriles and α-amino phosphonates , 2009 .

[31]  F. Bamoharram,et al.  A three component one-pot procedure for the synthesis of [1,2,4]triazolo/benzimidazolo-quinazolinone derivatives in the presence of H6P2W18O62 · 18H2O as a green and reusable catalyst , 2008, Molecular Diversity.

[32]  V. Alagarsamy,et al.  Synthesis and antihypertensive activity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones. , 2007, Bioorganic & medicinal chemistry.

[33]  A. Berkessel,et al.  Dramatic acceleration of olefin epoxidation in fluorinated alcohols: activation of hydrogen peroxide by multiple h-bond networks. , 2006, Journal of the American Chemical Society.

[34]  C. Kappe,et al.  Microwave-assisted three-component synthesis of 7-aryl-2-alkylthio-4,7-dihydro-1,2,4-triazolo[1,5-a]-pyrimidine-6-carboxamides and their selective reduction. , 2006, Journal of combinatorial chemistry.

[35]  V. Alagarsamy.  Synthesis and pharmacological investigation of some novel 2-methyl-3-(substituted methylamino)-(3H)-quinazolin-4-ones as histamine H1-receptor blockers. , 2004, Die Pharmazie.

[36]  B. Crousse,et al.  Fluorinated Alcohols: A New Medium for Selective and Clean Reaction , 2004 .

[37]  V. Alagarsamy,et al.  AntiHIV, Antibacterial And Antifungal Activities Of Some 2,3-Disubstituted Quinazolin-4(3H)-Ones , 2004 .

[38]  V. Alagarsamy,et al.  Synthesis, analgesic, anti-inflammatory and antibacterial activities of some novel 2-methyl-3-substituted quinazolin-4-(3H)-ones. , 2003, Biological & pharmaceutical bulletin.

[39]  H. Schmickler,et al.  Baeyer-Villiger oxidations with hydrogen peroxide in fluorinated alcohols: lactone formation by a nonclassical mechanism. , 2002, Angewandte Chemie.

[40]  V. Alagarsamy,et al.  Synthesis, analgesic, anti-inflammatory and antibacterial activities of some novel 2-phenyl-3-substituted quinazolin-4(3H) ones. , 2002, Biological & pharmaceutical bulletin.

[41]  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.

[42]  K. Gubernator,et al.  Pyrimido[1,6-a]benzimidazoles: a new class of DNA gyrase inhibitors. , 1992, Journal of medicinal chemistry.