Efficient synthesis of bicyclo[3.3.1]nonane systems via tandem 1,3-dinucleophilic addition of 4-hydroxy-2-quinolinones to quinolinium salts

Synthetic Communications

Volumn 42, Issue 13, 2012, Pages 1941-1949

  Moghaddam, Firouz Matloubi ^a   Mirjafary, Zohreh ^a   Saeidian, Hamdollah ^a,b   Foroushani, Behzad Koushki ^a   Nourian, Saghar ^a  

^a SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

^b PAYAME NOOR UNIVERSITY   (Iran)

Author keywords

1,3 dinucleophilic addition; Benzoxazocines; quinolinium salts; quinolinones

Indexed keywords

2 BENZYL 2 (4 BROMOBENZYL) 2,8,9,14 TETRAHYDRO 1H 8,14 METHANOQUINO (4,3 DEXTRO) (3,1) BENZOXAZOCIN 1 ONE; 2 BENZYL 9 ETHYL 2,8,9,14 TETRAHYDRO 1H 8,14 METHANOQUINO (4,3 DEXTRO) (3,1) BENZOXAZOCIN 1 ONE; 2 BENZYL 9 METHYL 2,8,9,14 TETRAHYDRO 1H 8,14 METHANOQUINO (4,3 DEXTRO) (3,1) BENZOXAZOCIN 1 ONE; 2 BENZYLY 9, 12 DIMETHYL 2,8,9,14 TETRAHYDRO 1H 8,14 METHANOQUINO (4,3 DEXTRO) (3,1) BENZOXAZOCIN 1 ONE; 2,8,9 TRIMETHYL 2,8,9,14 TETRAHYDRO 1H 8,14 METHANOQUINO (4,3 DEXTRO) (3,1) BENZOXAZOCIN 1 ONE; 2,9 DIMETHYL 2,8,9,14 TETRAHYDRO 1H 8,14 METHANOQUINO (4,3 DEXTRO) (3,1) BENZOXAZOCIN 1 ONE; 2,9,12 TRIMETHYL 2,8,9,14 TETRAHYDRO 1H 8,14 METHANOQUINO (4,3 DEXTRO) (3,1) BENZOXAZOCIN 1 ONE; 4 HYDROXY 2 QUINOLINONE DERIVATIVE; 9 ALLYL 2 METHYL 2,8,9,14 TETRAHYDRO 1H 8,14 METHANOQUINO (4,3 DEXTRO) (3,1) BENZOXAZOCIN 1 ONE; 9 BENZYL 2 METHYL 2,8,9,14 TETRAHYDRO 1H 8,14 METHANOQUINO (4,3 DEXTRO) (3,1) BENZOXAZOCIN 1 ONE; 9 ETHYL 2 METHYL 2,8,9,14 TETRAHYDRO 1H 8,14 METHANOQUINO (4,3 DEXTRO) (3,1) BENZOXAZOCIN 1 ONE; ETHYL [2 METHYL 1 OXO 2,14 DIHYDRO 1H 8,14 METHANOQUINO (4,3 DEXTRO) BENZOXACIN 9 YL] ACETATE; QUINOLINIUM SALT; QUINOLINOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 84859179053     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.550703     Document Type: Article

References (18)

1. Hajdok, S.; Conrad, J.; Leutbecher, H.; Strobel, S.; Schleid, T.; Beifuss, U. The Laccase-catalyzed domino reaction between catechols and heterocyclic 1,3-dicarbonyls and the unambiguous structure elucidation of the products by NMR spectroscopy and X-ray crystal structure analysis. J. Org. Chem. 2009, 74, 7230.
2. Arya, K.; Agarwal, M. Microwave-prompted multigram synthesis, structural determination, and photo-antiproliferative activity of fluorinated 4-hydroxyquinolinones. Bioorg. Med. Chem. Lett. 2007, 17, 86.
3. Mitscher, L. A. Bacterial topoisomerase inhibitors: Quinolone and pyridone antibacterial agents. Chem. Rev. 2005, 105, 559.
4. Afonso, A.; Weinstein, J.; Gentles, M. J. Antiviral compounds and antihypertensive compounds. PCT Int. Appl. WO9204327, 1993.
5. Morsay, A. M.; Lerson, P. D. 30-(Arylmethyl)-and 30-(aryloxy)-3-phenyl-4- hydroxyquinolin-2(1H)-ones: Orally active antagonists of the glycine site on the NMDA receptor. J. Med. Chem. 1994, 37, 1402.
6. Freeman, G. A.; Andrews, III, C. W.; Hopkins, A. L.; Lowell, G. S.; Schaller, L. T.; Cowan, J. R.; Gonzales, S. S.; Koszalka, G. W.; Hazen, R. J.; Boone, L. R.; Ferris, R. G.; Creech, K. L.; Roberts, G. B.; Short, S. A.; Weaver, K.; Reynolds, D. J.; Milton, J.; Ren, J.; Stuart, D. I.; Stammers, D. K.; Chan, J. H. Design of non-nucleoside inhibitors of HIV-1 reverse transcriptase with improved drug resistance properties. J. Med. Chem. 2004, 47, 5923.
7. Smit, R. G. Identification and initial structure-activity relationships of a novel nonpeptide quinolone GnRH receptor antagonist. Bioorg. Med. Chem. Lett. 1999, 9, 2615.
8. Watters, W. H.; Ramachandran, V. N. Synthesis of pyrano[3,2-c]quinolin-5- one alkaloids: Veprisine, 7-dimethylallyloxy-N-methylflindersine, and cis-3,4-dihydroxy-7-methoxy-2,2,6-trimethyl-3,4,5,6-tetrahydro-2H-pyrano[3,2-c] quinolin-5-one. J. Chem. Res., Synop. 1997, 184.
9. Naskar, B.; Saha, P.; Paira, R.; Hazra, A.; Paira, P.; Mondal, S.; Maity, A.; Sahu, K. B.; Banerjee, S.; Mondal, N. B. Synthesis of polycyclic fused 2-quinolones in aqueous micellar system. Tetrahedron Lett. 2010, 51, 1437.
10. Majumdar, K. C.; Pal, A. K.; Taher, A.; Debnath, P. Highly effective regioselective method for the synthesis of substituted coumarin-and quinolone-annulated heterocycles using a palladium(0)-catalyzed reaction. Synthesis 2007, 1707.
11. Mishra, J. K.; Samanta, K.; Jain, M.; Dikshit, M.; Panda, G. Amino acid-based enantiomerically pure 3-substituted benzofused heterocycles: A new class of antithrombotic agents. Bioorg. Med. Chem. Lett. 2010, 20, 244.
12. Seto, S.; Tanioka, A.; Ikeda, M.; Izawa, S. 2-Substituted-4-aryl-6,7,8,9- tetrahydro-5Hpyrimido[ 4,5-b][1,5]oxazocin-5-one as a structurally new NK1 antagonist. Bioorg. Med. Chem. Lett. 2005, 15, 1485.
13. Xu, Y. J.; Liu, H.; Pan, W.; Chen, X.; Wong, W. C.; Labelle, M. Improved synthesis of functionalized 5,6-dihydro-pyrimido[4,5-b][1,4]oxazepines. Tetrahedron Lett. 2005, 46, 7523.
14. Moghaddam, F. M.; Mirjafary, Z.; Saeidian, H.; Taheri, S.; Khodabakhshi, M. R. A new and convenient approach to heterotetracyclic benzoxazocines through addition of 1,3-dicarbonyl compounds to quinolinium salts. Tetrahedron Lett. 2010, 51, 2704, and references cited therein.
15. Kersten, L.; Taylor, R. H.; Felpin, F. X. Synthesis of spiro-pyridones and spiroquinolones by sequential palladium on carbon-catalyzed allylation and ring-closing metathesis reactions. Tetrahedron Lett. 2009, 50, 506.
16. Zhang, S. L.; Huang, Z. S.; Li, Y. M.; Chan, A. S. C.; Gu, L. Q. Synthesis of zwitterionic 4-hydroxy-2(1H)-quinolinone derivatives. Tetrahedron 2008, 64, 4403.
17. Pirrung, M. C.; Blume, F. Rhodium-mediated dipolar cycloaddition of diazoquinolinediones. J. Org. Chem. 1999, 64, 3642.
18. Diaba, F.; Houerou, C. L.; Grignon, M.; Gerval, P. Organosilicon entry to the regioselective cyanomethylation of quinolinium methiodides. J. Org. Chem. 2000, 65, 907.