메뉴 건너뛰기




Volumn 40, Issue 5, 2010, Pages 632-641

Facile and one-pot synthesis of 1,2-dihydroquinazolin-4(3H)-ones via tandem intramolecular pinner/dimroth rearrangement

Author keywords

Aromatic aldehyde; Aromatic o aminonitrile; Catalyst; Cyclocondensation; One pot synthesis

Indexed keywords

1,2 DIHYDROQUINAZOLIN 4(3H) ONE DERIVATIVE; ALDEHYDE; LEWIS ACID; N,N DIMETHYLFORMAMIDE; QUINAZOLINONE DERIVATIVE; UNCLASSIFIED DRUG; ZINC CHLORIDE;

EID: 76349100720     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902908822     Document Type: Article
Times cited : (33)

References (37)
  • 1
    • 33846523617 scopus 로고    scopus 로고
    • Targeted anti-mitotic therapies: Can we improve on tubulin agents? Nature reviews
    • (a) Jackson, J. R.; Patrick, D. R.; Dar, M. M.; Huang, P. S. Targeted anti-mitotic therapies: Can we improve on tubulin agents? Nature reviews. Cancer 2007, 7, 107-117;
    • (2007) Cancer , vol.7 , pp. 107-117
    • Jackson, J.R.1    Patrick, D.R.2    Dar, M.M.3    Huang, P.S.4
  • 2
    • 33847356832 scopus 로고    scopus 로고
    • Molecular-docking-guided design, synthesis, and biologic evaluation of radioiodinated quinazolinone prodrugs
    • DOI 10.1021/jm060944k
    • (b) Chen, K.; Al Aowad, A. F.; Adelstein, S. J.; Kassis, A. I. Molecular-docking-guided design, synthesis, and biologic evaluation of radioiodinated quinazolinone prodrugs. J. Med. Chem. 2007, 50 (4), 663-673; (Pubitemid 46332979)
    • (2007) Journal of Medicinal Chemistry , vol.50 , Issue.4 , pp. 663-673
    • Chen, K.1    Al Aowad, A.F.2    Adelstein, S.J.3    Kassis, A.I.4
  • 3
    • 33947264285 scopus 로고    scopus 로고
    • Evaluation of chemical, physical, and biologic properties of tumor-targeting radioiodinated quinazolinone derivative
    • (c) Wang, K.; Kirichian, A. M.; Al Aowad, A. F.; Adelstein, S. J.; Kassis, A. I. Evaluation of chemical, physical, and biologic properties of tumor-targeting radioiodinated quinazolinone derivative. Bioconjugate Chem. 2007, 18 (3), 754-764;
    • (2007) Bioconjugate Chem. , vol.18 , Issue.3 , pp. 754-764
    • Wang, K.1    Kirichian, A.M.2    Al Aowad, A.F.3    Adelstein, S.J.4    Kassis, A.I.5
  • 5
    • 0021999825 scopus 로고
    • Studies on 4(1H)-quinazolinones 5: Synthesis and anti-inflammatory activity of 4(1H)-quinazolinone derivatives
    • (e) 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 (5), 568-657;
    • (1985) J. Med. Chem. , vol.28 , Issue.5 , pp. 568-657
    • Ozaki, K.1    Yamada, Y.2    Oine, T.3    Ishizuka, T.4    Iwasawa, Y.5
  • 6
    • 0014472534 scopus 로고
    • Derivatives of dihydrobenzothiadiazine and tetrahydro-4-quinazolinone and their hydrogenolysis products: Preliminary study on their diuretic activity
    • (f) Biressi, M. D.; Cantarelli, G.; Carissimi, M.; Cattaneo, A.; Ravenna, F. Derivatives of dihydrobenzothiadiazine and tetrahydro-4-quinazolinone and their hydrogenolysis products: Preliminary study on their diuretic activity. Farmaco 1969,24, 199;
    • (1969) Farmaco , vol.24 , pp. 199
    • Biressi, M.D.1    Cantarelli, G.2    Carissimi, M.3    Cattaneo, A.4    Ravenna, F.5
  • 7
    • 76349116317 scopus 로고
    • Method to alter or control the development and/or the life cycle of various plant species
    • US Patent 4,431,440
    • (g) Bhalla, P. R.; Walworth, B. L. Method to alter or control the development and/or the life cycle of various plant species. US Patent 4,431,440, 1981;
    • (1981)
    • Bhalla, P.R.1    Walworth, B.L.2
  • 8
    • 0030048231 scopus 로고    scopus 로고
    • Antitumor 2,3-dihydro-2-(aryl)-4 (1H)-quinazolinone derivatives: Interactions with tubulin
    • (h) Hamel, E.; Lin, C. M.; Plowman, J.; Wang, H. K.; Lee, K. H.; Paull, K. D. Antitumor 2,3-dihydro-2-(aryl)-4 (1H)-quinazolinone derivatives: Interactions with tubulin. Biochem. Pharmacol. 1996, 51, 53-59.
    • (1996) Biochem. Pharmacol. , vol.51 , pp. 53-59
    • Hamel, E.1    Lin, C.M.2    Plowman, J.3    Wang, H.K.4    Lee, K.H.5    Paull, K.D.6
  • 9
    • 0035665655 scopus 로고    scopus 로고
    • Greenish-yellow electroluminescent devices using a novel dihydroquinazolinone derivative as emitting layer
    • Wang, S.; Lou, H.; Liu, Y. Q.; Yu, G.; Lu, P.; Zhu, D. B. Greenish-yellow electroluminescent devices using a novel dihydroquinazolinone derivative as emitting layer. J. Mater. Chem. 2001, 11, 2971-2973.
    • (2001) J. Mater. Chem. , vol.11 , pp. 2971-2973
    • Wang, S.1    Lou, H.2    Liu, Y.Q.3    Yu, G.4    Lu, P.5    Zhu, D.B.6
  • 10
    • 0001406449 scopus 로고
    • The synthesis of alkylketodihydroquinazolines from anthranilic nitrile
    • (a) Bogert, M. T.; Hand, W. F. The synthesis of alkylketodihydroquinazolines from anthranilic nitrile. J. Am. Chem. Soc. 1902, 24, 1031-1050;
    • (1902) J. Am. Chem. Soc. , vol.24 , pp. 1031-1050
    • Bogert, M.T.1    Hand, W.F.2
  • 11
    • 0002668497 scopus 로고
    • 3,5-Bibrom-2-aminobenzoic acid: Its nitrile and the synthesis of quinazolines from the latter
    • (b) Bogert, M. T.; Hand, W. F. 3,5-Bibrom-2-aminobenzoic acid: Its nitrile and the synthesis of quinazolines from the latter. J. Am. Chem. Soc. 1903, 25, 935-947;
    • (1903) J. Am. Chem. Soc. , Issue.25 , pp. 935-947
    • Bogert, M.T.1    Hand, W.F.2
  • 12
    • 33947471098 scopus 로고
    • The dimerization of 2-amino-5-nitrobenzonitrile
    • (c) Taylor, E. C; Knopf, R. J.; Borror, A. L. The dimerization of 2-amino-5-nitrobenzonitrile. J. Am. Chem. Soc. 1960, 82, 3152-3157;
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 3152-3157
    • Taylor, E.C.1    Knopf, R.J.2    Borror, A.L.3
  • 13
    • 0001406449 scopus 로고
    • The synthesis of alkylketodihydroquinazolines from anthranilic nitrile
    • (d) Bogert, M. T.; Hand, W. F. The synthesis of alkylketodihydroquinazolines from anthranilic nitrile. J. Am. Chem. Soc. 1902, 24, 1031-1050;
    • (1902) J. Am. Chem. Soc. , vol.24 , pp. 1031-1050
    • Bogert, M.T.1    Hand, W.F.2
  • 14
    • 37049057311 scopus 로고
    • Syntheses in the quinazolone series, part IV: The conversion of N-aroylorthanilamides into 2-arylquinazol-4-ones
    • (e) Stephen, H.; Wadge, G. Syntheses in the quinazolone series, part IV: The conversion of N-aroylorthanilamides into 2-arylquinazol-4-ones. J. Chem. Soc. 1956, 4420-4421.
    • (1956) J. Chem. Soc. , pp. 4420-4421
    • Stephen, H.1    Wadge, G.2
  • 15
    • 33847089574 scopus 로고
    • Iminoke-tene cycloaddition 2: Total syntheses of arborine, glycosminine, and rutecarpine by condensation of iminoketene with amides
    • (a) Kametani, T.; Loc, C. V.; Higa, T.; Koizumi, M.; Ihara, M.; Fukumoto, K. Iminoke-tene cycloaddition, 2: Total syntheses of arborine, glycosminine, and rutecarpine by condensation of iminoketene with amides. J. Am. Chem. Soc. 1977, 99, 2306-2309;
    • (1977) J. Am. Chem. Soc. , Issue.99 , pp. 2306-2309
    • Kametani, T.1    Loc, C.V.2    Higa, T.3    Koizumi, M.4    Ihara, M.5    Fukumoto, K.6
  • 16
    • 0030575412 scopus 로고    scopus 로고
    • Dimerization of substituted 2-aminobenzoic acids under Vilsmeier conditions: A novel route to the synthesis of 4-(3H)-quinazolinones
    • (b) Majo, V. J.; Perumal, P. T. Dimerization of substituted 2-aminobenzoic acids under Vilsmeier conditions: A novel route to the synthesis of 4-(3H)-quinazolinones. Tetrahedron Lett. 1996, 37, 5015-5018;
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5015-5018
    • Majo, V.J.1    Perumal, P.T.2
  • 17
    • 33750924793 scopus 로고    scopus 로고
    • Synthesis and application of quinazoline\-oxazoline-containing (quinazox) ligands
    • (c) Fekner, T.; Muller-Bunz, H.; Guiry, P. J. Synthesis and application of quinazoline\-oxazoline-containing (quinazox) ligands. Org. Lett. 2006, 8 (22), 5109-5112;
    • (2006) Org. Lett. , vol.8 , Issue.22 , pp. 5109-5112
    • Fekner, T.1    Muller-Bunz, H.2    Guiry, P.J.3
  • 19
    • 0024464547 scopus 로고
    • Use of new phosphonylating and coupling agents in the synthesis of oligodeoxyribonucleotides via the H-phosphonate approach
    • (a) Takeuchi, H.; Haguvara, S.; Eguchi, S. Use of new phosphonylating and coupling agents in the synthesis of oligodeoxyribonucleotides via the H-phosphonate approach. Tetrahedron Lett. 1989, 45, 6375-6378;
    • (1989) Tetrahedron Lett. , vol.45 , pp. 6375-6378
    • Takeuchi, H.1    Haguvara, S.2    Eguchi, S.3
  • 20
    • 0001695638 scopus 로고
    • Novel ring enlargement of lactams via quinazolinone annelation: A facile route to benzoanne-lated large-membered cyclic 1,5-diamines
    • (b) Takeuchi, H.; Haguvara, S.; Eguchi, S. Novel ring enlargement of lactams via quinazolinone annelation: A facile route to benzoanne-lated large-membered cyclic 1,5-diamines. J. Org. Chem. 1991, 56, 1535-1537.
    • (1991) J. Org. Chem. , vol.56 , pp. 1535-1537
    • Takeuchi, H.1    Haguvara, S.2    Eguchi, S.3
  • 22
    • 0001675757 scopus 로고
    • The chemistry of P-enaminoni-triles as versatile reagents in heterocyclic synthesis
    • (b) Erian, A. W. The chemistry of P-enaminoni-triles as versatile reagents in heterocyclic synthesis. Chem. Rev. 1993, 93, 1991-2005.
    • (1993) Chem. Rev. , vol.93 , pp. 1991-2005
    • Erian, A.W.1
  • 23
    • 0036994470 scopus 로고    scopus 로고
    • Activated nitriles in heterocyclic synthesis: Synthesis of new [1]benzopyrano[3',4':5 6]pyrano[2,3-d]pyrimidine and [1]benzopyrano[3',4':5,6] pyrano [3,2-e][1]triazolo [1,5-c]pyrimidine derivatives with promising antibacterial activity
    • Abd El-Wahab, A. H. F. Activated nitriles in heterocyclic synthesis: Synthesis of new [1]benzopyrano[3',4':5,6]pyrano[2,3-d]pyrimidine and [1]benzopyrano[3',4':5,6]pyrano [3,2-e][1]triazolo [1,5-c]pyrimidine derivatives with promising antibacterial activity. Acta Pharm. 2002, 54, 269-280.
    • (2002) Acta Pharm. , vol.54 , pp. 269-280
    • Abd El-Wahab, A.H.F.1
  • 24
    • 0035798209 scopus 로고    scopus 로고
    • A novel method of synthesis of 2 4-diamino-6-arylmethylqui-nazolines using palladium(0)-catalyzed organozinc chemistry
    • (a) Rosowsky, A.; Chen, H. A novel method of synthesis of 2,4-diamino-6-arylmethylqui-nazolines using palladium(0)-catalyzed organozinc chemistry. J. Org. Chem. 2001, 66, 7522-7526;
    • (2001) J. Org. Chem. , Issue.66 , pp. 7522-7526
    • Rosowsky, A.1    Chen, H.2
  • 25
    • 57249093602 scopus 로고    scopus 로고
    • Reaction of 3-cyano-2-amino-4, 5, 6,7-tetrahydrobenzo[6]thiophene with enaminonitriles
    • (b) Mohareb, R. M.; Al-Omran, F. A. Reaction of 3-cyano-2-amino-4,5,6,7- tetrahydrobenzo[6]thiophene with enaminonitriles. Monatsh. Chem. 2002, 133, 1443-1452;
    • (2002) Monatsh. Chem. , vol.133 , pp. 1443-1452
    • Mohareb, R.M.1    Al-Omran, F.A.2
  • 26
    • 0041317250 scopus 로고    scopus 로고
    • Ring forming reactions of imines of 2-aminoben-zaldehyde and related compounds
    • (c) Wiklund, P.; Bergman, J. Ring forming reactions of imines of 2-aminoben-zaldehyde and related compounds. Org. Biomol. Chem. 2003, 1, 367-372.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 367-372
    • Wiklund, P.1    Bergman, J.2
  • 27
    • 0345616432 scopus 로고    scopus 로고
    • Design, synthesis, and pharmacological profile of novel fused pyrazolo[4,3-d]pyridine and pyrazolo[3,4-b][1,8]naphthyridine iso-steres: A new class of potent and selective acetylcholinesterase inhibitors
    • Barreiro, E. J.; Camara, C. A.; Verli, H.; Brazil-Mas, L.; Castro, N. G.; Cintra, W. M.; Aracava, Y.; Rodrigues, C. R.; Fraga, C. A. M. Design, synthesis, and pharmacological profile of novel fused pyrazolo[4,3-d]pyridine and pyrazolo[3,4-b][1,8]naphthyridine iso-steres: A new class of potent and selective acetylcholinesterase inhibitors. J. Med. Chem. 2003, 46 (7), 1144-1152.
    • (2003) J. Med. Chem. , vol.46 , Issue.7 , pp. 1144-1152
    • Barreiro, E.J.1    Camara, C.A.2    Verli, H.3    Brazil-Mas, L.4    Castro, N.G.5    Cintra, W.M.6    Aracava, Y.7    Rodrigues, C.R.8    Fraga, C.A.M.9
  • 28
    • 0008359132 scopus 로고    scopus 로고
    • A new synthesis of aryl substituted quinazolin-4(1H)-ones
    • (a) Roth, G. A.; Tai, J. J. A new synthesis of aryl substituted quinazolin-4(1H)-ones. J. Heterocycl. Chem. 1996, 33, 2051-2053;
    • (1996) J. Heterocycl. Chem. , vol.33 , pp. 2051-2053
    • Roth, G.A.1    Tai, J.J.2
  • 29
    • 76349113394 scopus 로고    scopus 로고
    • Quinazolinone and benzoxazine derivatives as progesterone receptor modulators
    • (b) Grubs, G. S.; Zhi, L.; Jones, T. K.; Marschke, K. B.; Tegley, C. M. Quinazolinone and benzoxazine derivatives as progesterone receptor modulators. PCT Int. Appl. WO 2,000,066,560, 2000.
    • (2000) PCT Int. Appl. WO , vol.2000 , Issue.66 , pp. 560
    • Grubs, G.S.1    Zhi, L.2    Jones, T.K.3    Marschke, K.B.4    Tegley, C.M.5
  • 30
    • 0033677513 scopus 로고    scopus 로고
    • Synthesis of quinazolines using carbon dioxide (or carbon monoxide with sulfur) under mild conditions
    • DOI 10.1002/1098-1071(2000)11:6<428::AID-HC12>3.0.CO;2-Z
    • (a) Mizuno, T.; Okamoto, N.; Ho, T.; Miyata, T. Synthesis of quinazolines using carbon dioxide (or carbon monoxide with sulfur) under mild conditions. Heteroatom Chem. 2000, 11, 428-433; (Pubitemid 30957838)
    • (2000) Heteroatom Chemistry , vol.11 , Issue.6 , pp. 428-433
    • Mizuno, T.1    Okamoto, N.2    Ito, T.3    Miyata, T.4
  • 31
    • 38949133257 scopus 로고    scopus 로고
    • Synthesisofquinazolinesbythe carbonylation using carbon dis-ulfide under mild conditions
    • (b) Mizuno, T. Synthesisofquinazolinesbythe carbonylation using carbon dis-ulfide under mild conditions. Kagaku to Kogyo. 2002, 76, 431-434;
    • (2002) Kagaku to Kogyo , vol.76 , pp. 431-434
    • Mizuno, T.1
  • 32
    • 4444357002 scopus 로고    scopus 로고
    • The simple solvent-free synthesis of1H-quinazoline-2,4-diones using supercritical carbon dioxide and catalytic amount of base
    • (c) Mizuno, T.; Iwai, T.; Ishino, Y. The simple solvent-free synthesis of1H-quinazoline-2,4-diones using supercritical carbon dioxide and catalytic amount of base. Tetrahedron Lett. 2004, 45, 7073-7075.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 7073-7075
    • Mizuno, T.1    Iwai, T.2    Ishino, Y.3
  • 33
    • 4344679369 scopus 로고    scopus 로고
    • An elegant synthesis of quino[2,3-a]carbazoles and their antibacterial studies
    • Danish, I. A.; Prasad, K. J. R. An elegant synthesis of quino[2,3-a]carbazoles and their antibacterial studies. Indian J. Chem. Sect. B. 2004, 43B, 1548-1552.
    • (2004) Indian J. Chem. Sect. B. , vol.43 B , pp. 1548-1552
    • Danish, I.A.1    Prasad, K.J.R.2
  • 36
    • 0001174653 scopus 로고
    • The chemistry of imidates
    • Roger, R.; Neilson, D. The chemistry of imidates. Chem. Rev. 1961, 61, 179-211.
    • (1961) Chem. Rev. , vol.61 , pp. 179-211
    • Roger, R.1    Neilson, D.2
  • 37
    • 27944434831 scopus 로고    scopus 로고
    • Synthesis and dimroth rearrangement of 3-amino-4-(5-amino-1H-1 2,3-triazol-1-yl)-1, 2,5-oxadiazoles
    • Rozhkov, V. Y.; Batog, L. V.; Shevtsova, E. K.; Struchkova, M. I. Synthesis and dimroth rearrangement of 3-amino-4-(5-amino-1H-1,2,3-triazol-1-yl) -1,2,5-oxadiazoles. Mendeleev Commun. 2004, 14, 76-77.
    • (2004) Mendeleev Commun. , vol.14 , pp. 76-77
    • Rozhkov, V.Y.1    Batog, L.V.2    Shevtsova, E.K.3    Struchkova, M.I.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.