Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 8
630
Views
79
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of 2,3-Dihydroquinazoline-4(1H)-ones

, &
Pages 1231-1242 | Received 21 Apr 2009, Published online: 12 Mar 2010

REFERENCES

  • (a) Jiang , J. B. ; Hesson , D. P. ; Dusak , B. A. ; Dexter , D. L. ; Kang , G. J. ; Hamel , E. Synthesis and biological evaluation of 2-styrylquinazolin-4(3H)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization . J. Med. Chem. 1990 , 33 , 1721 – 1728 ; (b) Ozaki , K. ; Yamada , Y. ; Oine , T. ; Ishizuka , T. ; Iwasawa , Y. Studies on 4(1H)-quinazolinones, 5: Synthesis and anti-inflammatory activity of 4(1H)-quinazolinone derivatives . J. Med. Chem. 1985 , 28 , 568 – 576 ; (c) Wolfe , J. F. ; Rathman , T. L. ; Sleevi , M. C. ; Campbell , J. A. ; Greenwood , T. D. Synthesis and anticonvulsant activity of some new 2-substituted 3-aryl-4(3H)-quinazolinones . J. Med. Chem. 1990 , 33 , 161 – 166 ; (d) Takaya , Y. ; Tasaka , H. ; Chiba , T. ; Uwai , K. ; Tanitsu , M. ; Kim , H. ; Wataya , Y. ; Miura , M. ; Takeshita , M. ; Oshima , Y. New type of febrifugine analogues, bearing a quinolizidine moiety, show potent antimalarial activity against plasmodium malaria parasite . J. Med. Chem. 1999 , 42 , 3163 – 3166 ; (e) Bridges , A. J. ; Zhou , H. ; Cody , D. R. ; Rewcastle , G. W. ; McMichael , A. ; Showalter , H. D. H. ; Fry , D. W. ; Kraker , A. J. ; Deny , W. A. Tyrosine kinase inhibitors, 8: An unusually steep structure−activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor . J. Med. Chem. 1996 , 39 , 267 – 276 ; (f) Kurogi , Y. ; Inoue , Y. ; Tsutsumi , K. ; Nakamura , S. ; Nagao , K. ; Yoshitsugu , H. ; Tsuda , Y. Synthesis and hypolipidemic activities of novel 2-[4-[(diethoxyphosphoryl)methyl]phenyl]quinazolines and 4(3H)-quinazolinones . J. Med. Chem. 1996 , 39 , 1433 – 1437 ; (g) Sadanadam , Y. S. ; Reddy , R. M. ; Bhaskar , A. Synthesis of substituted 2,3-dihydro-1-(β-phenylethyl)-2-aryl and 2,3-diaryl-4(1H)-quinazolinones and their pharmacological activities . Eur. J. Med. Chem. 1987 , 22 , 169 – 173 ; (h) Bonola , G. ; Sianesi , E. 2,3-Dihydro-4(1H)-quinazolinone derivatives . J. Med. Chem. 1970 , 13 , 329 – 332 ; (i) Hour , M. ; Huang , L. ; Kuo , S. ; Xia , Y. ; Bastow , K. ; Nakanishi , Y. ; Hamel , E. ; Lee , K. 6-Alkylamino- and 2,3-dihydro-3′-methoxy-2-phenyl-4-quinazolinones; and related compounds: Their synthesis, cytotoxicity; and inhibition of tubulin polymerization . J. Med. Chem. 2000 , 43 , 4479 – 4487 ; (j) Gupta , R. C. ; Nath , R. ; Shanker , K. ; Bhargava , K. P. ; Kishore , K. Amoebicidal and fungicidal activity of new quinozolones . J. Indian Chem. Soc. 1979 , 56 , 219 – 220 ; (k) Na , Y. H. ; Hong , S. H. ; Lee , J. H. ; Park , W. K. ; Baek , D. J. ; Koh , H. Y. ; Cho , Y. S. ; Choo , H. ; Pae , A. N. Novel quinazolinone derivatives as 5-HT7 receptor ligands . Bioorg. Med. Chem. 2008 , 16 , 2570 – 2578 .
  • Williams , R. ; Niswender , C. M. ; Luo , Q. ; Le , U. ; Conn , P. J. ; Lindsley , C. W. Positive allosteric modulators of the metabotropic glutamate receptor subtype 4 (mGluR4), part II: Challenges in hit-to-lead. Bioorg. Med. Chem. Lett. 2009, 19, 962–966.
  • Armarego , W. L. F. Quinazolines . Adv. Heterocycl. Chem. 1979 , 24 , 1 – 62 .
  • Segarra , V. ; Crespo , M. I. ; Pujol , F. ; Belata , J. ; Domenech , T. ; Miralpeix , M. ; Palacios , J. M. ; Castro , A. ; Martinez , A. Phosphodiesterase inhibitory properties of losartan design and synthesis of new lead compounds . Bioorg. Med. Chem. Lett. 1998 , 8 , 505 – 510 .
  • Yu , Y. ; Ostresh , J. M. ; Houghten , R. A. A traceless approach for the parallel solid-phase synthesis of 2-(arylamino)quinazolinones . J. Org. Chem. 2002 , 67 , 5831 – 5834 .
  • Kamal , A. ; Ramana , K. V. ; Ankati , H. B. ; Ramana , A. V. Mild and efficient reduction of azides to amines: Synthesis of fused [2,1-b]quinazolinones . Tetrahedron Lett. 2002 , 43 , 6861 – 6863 .
  • Staiger , R. P. ; Moyer , C. L. ; Pitcher , G. R. Isatoic anhydride: Reactions with isocyanates, isothiocyanates, and Schiff's base . J. Chem. Eng. Data 1963 , 8 , 454 – 456 .
  • Akazome , M. ; Yamamoto , J. ; Kondo , T. ; Watanabe , Y. Palladium complex–catalyzed intermolecular reductive N-heterocyclization: Novel synthesis of quinazoline derivatives from 2-nitrobenzaldehyde or 2-nitrophenyl ketones with formamide . J. Organoment. Chem. 1995 , 494 , 229 – 233 .
  • Baghbanzadeh , M. ; Salehi , P. ; Dabiri , M. ; Kozehgarya , G. Water-accelerated synthesis of novel bis-2,3-dihydroquinazolin-4(1H)-one derivatives . Synthesis 2006 , 2 , 344 – 348 .
  • (a) 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 ; (b) Dabiri , M. ; Salehi , P. ; Baghbanzadeh, Zolfigol , M. A. ; Agheb , M. ; Heydari , S. Silica sulfuric acid: An efficient reusable heterogeneous catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones in water and under solvent-free conditions . Catal. Commun. 2008 , 9 , 785 – 788 .
  • Dabiri , M. ; Salehi , P. ; Otokesh , S. ; Baghbanzadeh , M. ; Kozehgarya , G. ; Mohammadi , A. A. Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using KAl(SO4)2·2H2O as a reusable catalyst in water and ethanol . Tetrahedron Lett. 2005 , 46 , 6123 – 6126 .
  • 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 .
  • Wang , L.-M. ; Hu , L. ; Shao , J.-H. ; Yu , T. ; Zhang , L. A novel catalyst zinc(II) perfluorooctanoate [Zn(PFO)2]–catalyzed three-component one-pot reaction: Synthesis of quinazolinone derivatives in aqueous micellar media . J. Fluorine Chem. 2008 , 129 , 1139 – 1145 .
  • Chen , J. X. ; Wu , D. ; He , F. ; Liu , M. C. ; Wu , H. ; Ding , J. C. ; Su , W. K. Gallium(III) triflate–catalyzed one-pot selective synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones . Tetrahedron Lett. 2008 , 49 , 3814 – 3818 .
  • Surpur , M. P. ; Single , P. R. ; Patil , S. B. ; Samat , S. D. Expeditious one-pot and solvent-free synthesis of dihydroquinazolin-4(1H)-ones in the presence of microwaves . Synth. Commun. 2007 , 37 , 1965 – 1970 .
  • (a) Chen , J. X. ; Su , W. K. ; Wu , H. Y. ; Liu , M. C. ; Jin , C. Eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-ones in ionic liquids or ionic liquid–water without additional catalyst . Green Chem. 2007 , 9 , 972 – 975 ; (b) Shaabani , A. ; Rahmati , A. ; Moghimi , R. J. Ionic liquid–promoted synthesis of 3-(2′-benzothiazolo)-2,3-dihydroquinazolin-4(1H)-ones . C. R. Chimie. 2008 , 11 , 759 – 764 .
  • (a) Shaterian , H. R. ; Shahrekipoor , F. ; Ghashang , M. Silica-supported perchloric acid (HClO4–SiO2): A highly efficient and reusable catalyst for the protection of hydroxyl groups using HMDS under mild and ambient conditions . J. Mol. Catal. A: Chem. 2007 , 272 , 142 – 151 ; (b) Shaterian , H. R. ; Yarahmadi , H. ; Ghashang , M. Silica-supported perchloric acid (HClO4–SiO2): An efficient and recyclable heterogeneous catalyst for the one-pot synthesis of amidoalkyl naphthols . Tetrahedron 2008 , 64 , 1263 – 1269 ; (c) Shaterian , H. R. ; Yarahmadi , H. A modified reaction for the preparation of amidoalkyl naphthols . Tetrahedron Lett. 2008 , 49 , 1297 – 1300 ; (d) Shaterian , H. R. ; Hosseinian , A. ; Ghashang , M. A three-component novel synthesis of 1-carbamato-alkyl-2-naphthols derivatives . Tetrahedron Lett. 2008 , 49 , 5804 – 5806 ; (e) Shaterian , H. R. ; Hosseinian , A. ; Ghashang , M. Reaction in dry media: Silica gel–supported ferric chloride–catalyzed synthesis of 1,8-dioxo-octahydroxanthene derivatives . Phosphorus, Sulfur Silicon Relat. Elem. 2008 , 183 , 3136 – 3144 ; (f) Shaterian , H. R. ; Ghashang , M. ; Feyzi , M. Silica sulfuric acid as an efficient catalyst for the preparation of 2H-indazolo[2,1-b]phthalazine-triones . Appl. Catal. A: Gen. 2008 , 345 , 128 – 133 .
  • (a) Bharadwaj , S. K. ; Hussain , S. ; Kar , M. ; Chaudhuri , M. K. Al(H2PO4)3: An efficient catalyst for nitration of organic compounds with nitric acid . Catal. Commun. 2008 , 9 , 919 – 923 ; (b) Shaterian , H. R. ; Amirzadeh , A. ; Khorami , F. ; Ghashang , M. Environmentally friendly preparation of amidoalkyl naphthols . Synth. Commun. 2008 , 38 , 2983 – 2994 ; (c) Shaterian , H. R. ; Ghashang , M. ; Tajbakhsh Riki , N. ; Asadi , M. An efficient method for the silylation of hydroxyl groups with hexamethyldisilazine (HMDS) catalyzed by aluminum tris(dihydrogen phosphate) under solvent-free and ambient conditions . Can. J. Chem. 2008 , 86 , 841 – 845 ; (d) Shaterian , H. R. ; Hosseinian , A. ; Ghashang , M. Environmentally friendly preparation of 3,4-dihydropyrimidin-2(1H)-thiones catalyzed by Al(H2PO4)3 . Phosphorus, Sulfur, Silicon Relat. Elem. 2009 , 184 , 126 – 134 .
  • This article is dedicated to Professor Ahmad Akbari, Chancellor of Sistan and Baluchestan University, who dedicates himself to the progress of science.

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.