Synthesis and Antimicrobial Activity of 3-Cyano-4-imino-9-methoxy-4H-pyrimido [2, 1-b] pyrimido [4, 5-b] quinoline and 2-Substituted Derivatives

作者: S. P. Vartale , N. K. Halikar , Y. D. Pawar

DOI: 10.1155/2013/862651

关键词: QuinolineArylAntimicrobialCatalysisOrganic chemistryMethyleneAlcoholPhenolsChemistryMalononitrile

摘要: The 2-amino-7-methoxypyrimido[4,5-b]quinoline (1) on treatment with bis(methylthio)methylene malononitrile (2) in ethyl alcohol and catalytic amount of TEA gives 3-cyano-4-imino-9-methoxy-2-methythio-4H-pyrimido[2,1-b]pyrimido[4,5-b]quinoline (3). latter were further reacted selected N-, O-, C-nucleophiles such as aryl amines, hetryl substituted phenols, compounds containing an active methylene group.

参考文章(26)
G. M. Badger, The chemistry of heterocyclic compounds Academic Press. ,(1961)
T. H. Althuis, P. F. Moore, H. J. Hess, Development of ethyl 3,4-dihydro-4-oxopyrimido[4,5-b]quinoline-2-carboxylate, a new prototype with oral antiallergy activity. Journal of Medicinal Chemistry. ,vol. 22, pp. 44- 48 ,(1979) , 10.1021/JM00187A011
Haythem Saadeh, Ibrahim Mosleh, Mohammad Mubarak, Synthesis of novel hybrid molecules from precursors with known antiparasitic activity. Molecules. ,vol. 14, pp. 1483- 1494 ,(2009) , 10.3390/MOLECULES14041483
K. N. Dhawan, B. P. Jaju, G. P. Gupta, Validity of antagonism of different effects of reserpine as test for anti-depressant activity. Psychopharmacology. ,vol. 18, pp. 94- 98 ,(1970) , 10.1007/BF00402388
I. V. Ukrainets, Liu Yangyang, A. A. Tkach, A. V. Turov, 4-HYDROXY-2-QUINOLONES 166*. SYNTHESIS, ISOMERISM, AND ANTITUBERCULAR ACTIVITY OF 3-ARYLAMINOMETHYLENE- QUINOLINE-2,4-(1H,3H)-DIONES Chemistry of Heterocyclic Compounds. ,vol. 45, pp. 802- 808 ,(2009) , 10.1007/S10593-009-0356-X
Izzat T. Raheem, Steven N. Goodman, Eric N. Jacobsen, Catalytic asymmetric total syntheses of quinine and quinidine. Journal of the American Chemical Society. ,vol. 126, pp. 706- 707 ,(2004) , 10.1021/JA039550Y
C. H. Browning, J. B. Cohen, S. Ellingworth, R. Gulbransen, The antiseptic action of anil-pyridines and anil-quinolines The Journal of Pathology and Bacteriology. ,vol. 27, pp. 121- 122 ,(1924) , 10.1002/PATH.1700270115
G. Sivalingam, Giridhar Madras, Thermal Degradation of Poly(vinyl acetate) and Poly(epsilon-caprolactone) and Their Mixtures in Solution Industrial & Engineering Chemistry Research. ,vol. 43, pp. 1561- 1567 ,(2004) , 10.1021/IE034115Y
Maher F. El-Zohry, Abd El-Hamed N. Ahmed, Farghaly A. Omar, Mohamed A. Abd-Alla, Synthesis and antibacterial activity of certain quinoline and quinazoline derivatives containing sulfide and sulfone moieties. Journal of Chemical Technology & Biotechnology. ,vol. 53, pp. 329- 336 ,(2007) , 10.1002/JCTB.280530403
Mark P. Wentland, Suzanne C. Aldous, Monte D. Gruett, Robert B. Perni, Ronald G. Powles, Deborah W. Danz, Kristina M. Klingbeil, A.Danielle Peverly, Ronald G. Robinson, Thomas H. Corbett, James B. Rake, Susan A. Coughlin, The antitumor activity of novel pyrazoloquinoline derivatives Bioorganic & Medicinal Chemistry Letters. ,vol. 5, pp. 405- 410 ,(1995) , 10.1016/0960-894X(95)00044-T