Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 20
570
Views
72
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of New 2-Aryl Substituted 2,3-Dihydroquinazoline-4(1H)-ones Under Solvent-Free Conditions, Using Molecular Iodine as a Mild and Efficient Catalyst

, , , &
Pages 3567-3576 | Received 05 Feb 2008, Published online: 29 Sep 2008

REFERENCES

  • Farghaly , A. M. ; Soliman , R. ; Khalil , M. A. ; Bekhit , A. A. ; Bekhit , A. ; El-Din , A. Thioglycolic acid and pyrazole derivatives of 4(3H)-quinazolinone: Synthesis and antimicrobial evaluation . Boll. Chim. Farm . 2002 , 141 , 372 – 378 .
  • Parkanyi , C. ; Schmidt , D. S. Synthesis of 5-chloro-2-methyl-3-(5-methylthiazol-2-yl)-4(3H)-quinazolinone and related compounds with potential biological activity . J. Heterocycl. Chem. 2000 , 37 , 725 – 729 .
  • Hermecz , I. ; Kokosi , J. ; Podanyi , B. ; Szaz , G. Synthesis of indolyl-4(3H)-quinazolinones . Heterocycles 1994 , 37 , 903 – 914 .
  • Scovill , J. ; Blank , E. ; Konnick , M. ; Nenortas , E. ; Shapiro , T. Antitrypanosomal activities of tryptanthrins . Antimicrob. Agents Chemother. 2002 , 46 , 882 – 883 .
  • Fujimoto , H. ; Negishi , E. ; Yamaguchi , K. ; Nishi , N. ; Yamazaki , M. Isolation of new tremorgenic metabolites from an ascomycete, Corynascus setosus. Chem. Pharm. Bull. 1996, 44, 1843–1848.
  • Takahashi , C. ; Matsushita , T. ; Doi , M. ; Minoura , K. ; Shingu , T. ; Kumeda , Y. ; Numata , A. Fumiquinazolines A-G, novel metabolites of a fungus separated from a pseudolabrus marine fish . J. Chem. Soc., Perkin Trans. 1 1995 , 2345 – 2353 .
  • Hochlowski , J. E. ; Mullally , M. M. ; Spanton , S. G. ; Whitten , D. N. ; Hill , P. ; Mc Alpine , J. B. 5-Acetylardeemin, a novel heterocyclic compound which reverses multiple-drug resistance in tumor cells, 2: Isolation and elucidation of the structure of 5-N-acetylardeemin and 2 congrners . J. Antibiot. 1993 , 46 , 380 – 386 .
  • Hernandez , F. ; Buenadicha , F. L. ; Avendaño , C. ; Söllhuber , M. 1-Alkyl-2,4-dihydro-1H-yrazino[2,1-b]quinazoline-3,6-diones as glycine templates: Synthesis of fiscalin B . Tetrahedron: Asymmetry 2001 , 12 , 3387 – 3398 .
  • Penn , J. ; Mantle , P. G. ; Bilton , J. N. ; Sheppard , R. N. Glyantrypine, a novel anthranilic acid–containing metabolite of Aspergillus clavatus . J. Chem. Soc., Perkin Trans. 1 1992 , 1495 .
  • Eguchi , S. Quinazoline alkaloids and related chemistry . Top. Heterocycl. chem. 2006 , 6 , 113 – 156 , and references therein .
  • Merck Index, , 13th ed. ; Merck Publishing Group : Rahway , NJ , 2001 ; p. 5987 .
  • Kacker , I. K. ; Zaheer , S. H. Potential analgesics, part I: Synthesis of substituted 4-quinazolones . J. Indian Chem. Soc. 1951 , 28 , 344 – 346 .
  • Van Zyl , E. F. A survey of reported synthesis of methaqualone and some positional and structural isomers . Forensic Sci. Int. 2002 , 122 , 142 – 149 .
  • Connolly , D. J. ; Cusack , D. ; O'Sullivan , T. P. ; Guiry , P. J. Synthesis of quinazolinones and quinazolines . Tetrahedron 2005 , 61 , 10153 – 10202 .
  • Merck Index, , 13th ed. ; Merck Publishing Group : Rahway , NJ , 2001 ; p. 3749 .
  • Jackman , G. B. ; Petrow , V. ; Stephenson , O. Some 2,3-disubstituted 4(3H)-quinazolones and 3H-4-thioquinazolones . J. Pharm. Pharmacol. 1960 , 12 , 529 – 538 .
  • (a) Kim , K. M. ; Ryu , E. K. Unusual iodine catalyzed lactonization of gamma-methyl-gamma, deltapentenoic acids: A facile synthesis of gamma, gamma-dimethyl-gamma-butyrolactones . Tetrahedron Lett. 1996 , 37 , 1441 ; (b) Firouzabadi , H. ; Iranpoor , N. ; Hazarkhani , H. Iodine catalyzes efficient and chemoselective thioacetalization of carbonyl functions, transthioacetalization of O,O- and S,O-acetals and acylals . J. Org. Chem. 2001 , 66 , 7527 ; (c) Saeeng , R. ; Sirion , U. ; Sahakitpichan , P. ; Isobe , M. Iodine catalyzes C-glycosidation of D-glucal with silylacetylene . Tetrahedron Lett. 2003 , 44 , 6211 ; (d) Ke , B. ; Qin , Y. ; He , Q. ; Huang , Z. ; Wang , F. Preparation of bisindolylalkanes from N-tert-butanesulfinyl aldimines . Tetrahedron Lett. 2005 , 46 , 1751 – 1753 .
  • (a) Mukhopadhyay , C. ; Becker , F. F. ; Banik , B. K. A novel catalytic role of molecular iodine in the oxidation of benzylic alcohols: Microwave-assisted reaction . J. Chem. Res., Synop. 2001 , 28 – 31 ; (b) Yadav , J. S. ; Reddy , B. V. S. ; Sabitha , G. ; Reddy , G. S. K. K. Aromatization of Hantzsch 1,4-dihydropyridines with I2-MeOH . Synthesis 2000 , 1532 – 1534 ; (c) Basu , M. K. ; Samajdar , M. K. ; Becker , F. F. ; Banik , B. K. A new molecular iodine-catalyzed acetalization of carbonyl compounds . Synlett 2002 , 319 – 321 .
  • (a) Yadav , J. S. ; Reddy , B. V. S. ; Reddy , M. S. ; Prasad , A. R. Iodine as novel reagent for the 1,2-addition of trimethylsilyl cyanide to ketones including alpha,beta-unsaturated ketones . Tetrahedron Lett. 2002 , 43 , 9703 – 9706 ; (b) Bandgar , B. P. ; Shaikh , K. A. Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions . Tetrahedron Lett. 2003 , 44 , 1959 – 1961 ; (c) Banik , B. K. ; Fernandez , M. ; Alvarez , C. Iodine-catalyzed highly efficient Michael reaction of indoles under solvent-free condition . Tetrahedron Lett. 2005 , 46 , 2479 – 2482 .
  • (a) Das , B. ; Banerjee , J. ; Ramu , R. ; Pal , R. ; Ravindranath , N. ; Ramesh , C. Efficient, selective deprotection of aromatic acetates catalyzed by Amberlyst-15 or iodine . Tetrahedron Lett. 2003 , 44 , 5465 – 5468 ; (b) Yadav , J. S. ; Reddy , B. V. S. ; Shubashree , S. ; Sadashiv , K. Iodine/MeOH: A novel and efficient reagent system for thiocyanation of aromatics and heteroaromatics . Tetrahedron Lett. 2004 , 45 , 2951 – 2954 ; (c) Phukan , P. Iodine as an extremely powerful catalyst for the acetylation of alcohols under solvent-free conditions . Tetrahedron Lett. 2004 , 45 , 4785 – 4787 .
  • (a) Chu , C. ; Gao , S. ; Sastry , M. N. V. ; Yao , C. Iodine-catalyzed Michael addition of mercaptans to alpha,beta-unsaturated ketones under solvent-free conditions . Tetrahedron Lett. 2005 , 46 , 4971 – 4974 ; (b) Gao , S. ; Tzeng , T. ; Sastry , M. N. V. ; Chu , C. ; Liu , J. ; Lin , C. ; Yao , C. Iodine catalyzed conjugate addition of mercaptans to alpha,beta-unsaturated carboxylic acids under solvent-free condition . Tetrahedron Lett. 2006 , 47 , 1889 – 1893 ; (c) Lin , C. ; Hsu , J. ; Sastry , M. N. V. ; Fang , H. ; Tu , Z. ; Liu , J. ; Yao , C. I2-catalyzed Michael addition of indole and pyrrole to nitroolefins . Tetrahedron 2005 , 61 , 11751 – 11757 .
  • Yadav , J. S. ; Reddy , B. V. S. ; Reddy , M. S. Elemental iodine-catalyzed coupling of alkynylsilanes with acid chlorides: A facile synthesis of alpha, beta-acetylenic ketones . Synlett 2003 , 1722 – 1724 .
  • Yadav , J. S. ; Reddy , B. V. S. ; Rao , C. V. ; Rao , K. V. Elemental iodine catalyzed [4 + 2] cycloaddition reactions of o-quinomethanes: An efficient synthesis of trans-fused pyrano[3,2-c]benzopyrans . J. Chem. Soc., Perkin. Trans. 1 2002 , 1401 – 1404 .
  • (a) Firouzabadi , H. ; Iranpoor , N. ; Sobhani , S. A high yielding preparation of alphatrimethylsilyloxyphosphonates by silylation of alpha-hydroxyphosphonates with HMDS catalyzed by iodine . Tetrahedron Lett. 2002 , 43 , 3653 .
  • (a) Varala , R. ; Nuvula , S. ; Adapa , S. R. Molecular iodine–catalyzed facile procedure for N-boc protection of amines . J. Org. Chem. 2006 , 71 , 8283 – 82868 ; (b) Lokhande , P. D. ; Sakate , S. S. ; Taksande , K. N. ; Navghare , B. Dimethylsulfoxide-iodine catalysed deprotection of 2′-allyloxychalcones: Synthesis of flavones . Tetrahedron Lett. 2005 , 46 , 1573 – 1574 .
  • (a) Bhosale , R. S. ; Bhosale , S. V. ; Bhosale , S. V. ; Wang , T. ; Zubaidha , P. K. An efficient, high yield protocol for the one-pot synthesis of dihydropyrimidin-2(1H)-ones catalyzed by iodine . Tetrahedron Lett. 2004 , 45 , 9111 ; (b) Lee , B. S. ; Mahajan , S. ; Janda , K. D. Molecular iodine-catalyzed imine activation for three-component nucleophilic addition reactions . Synlett 2005 , 1325 ; (c) Lin , C. ; Fang , H. ; Tu , Z. ; Liu , J. ; Yao , C. Stereoselective three-component synthesis of trans-endo-decahydroquinolin-4-one derivatives from aldehydes, aniline, and acetylcyclohexene . J. Org. Chem. 2006 , 71 , 6588 .
  • Su , W. ; Yang , B. Reductive cyclization of nitro and azide compounds with aldehydes and ketones promoted by metallic samarium and catalytic amount of iodine. Aust. J. Chem. 2002, 55, 695–697.
  • Domling , A. Recent advances in isocyanide-based multicomponent chemistry . Curr. Opin. Chem. Biol. 2002 , 6 , 306 – 313 .
  • Dabiri , M. ; Salehi , P. ; Mohammadi , A. A. ; Baghbanzadeh , M. One-pot synthesis of mono- and disubstituted (3H)-quinazolin-4-ones in dry media under microwave irradiation . Synth. Commun. 2005 , 35 , 279 – 287 .
  • Salehi , P. ; Dabiri , M. ; Zolfigol , M. A. ; Baghbanzadeh , M. A novel method for the one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones . Synlett 2005 , 1155 – 1157 .
  • Salehi , P. ; Dabiri , M. ; Baghbanzadeh , M. ; Bahramnejad , M. One-pot, three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones by montmorillonite K-10 as an efficient and reusable catalyst . Synth. Commun. 2006 , 36 , 2287 – 2292 .
  • Surpur , M. P. ; Singh , P. R. ; Patil , S. B. ; Samant , S. D. Expeditious one-pot and solvent-free synthesis of dihydroquinazolin-4(1H)-ones in the presence of microwaves . Synth. Commun. 2007 , 1965 – 1970 .
  • Baghbanzadeh , M. ; Salehi , P. ; Dabiri , M. ; Kozehgary , G. Water-accelerated synthesis of novel bis-2,3-dihydroquinazolin-4(1H)-one derivatives . Synthesis 2006 , 344 – 348 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.