Journal of Pharmacy Research Vol.5 Issue 5.May 2012 Sambhaji P. Vartale et al. / Journal of Pharmacy Research 2012,5(5),2672-2675 2672-2675 Research Article ISSN: 0974-6943 Available online through http://jprsolutions.info * Corresponding author. Dr.Sambhaji P. Vartale, P.G. Research Centre, Department of Chemistry, Yeshwant Mahavidyalaya, VIP Road, Nanded-431602, Maharashtra state, India. Design synthesis, reactions and pharmacological properties of some novel fused pyrimido [1, 2-a] quinolines moiety Sambhaji P. Vartale*, Nilesh K. Halikar & Yogesh D Pawar P.G. Research centre,Department of chemistry,Yeshwant Mahavidyalaya,Nanded-431602(MS)India. Received on:11-01-2012; Revised on: 17-02-2012; Accepted on:19-04-2012 ABSTRACT 2-Amino-3-cyano quinoline (1) and bis (methylthio) methylene malononitrile (2) were refluxed in N,N-dimethyl formamide (DMF) in presence of catalytic amount of anhydrous potassium carbonate to afford 3, 11-dicyano-4-imino-2-methylthio -4H-pyrimido [1, 2-a] quinoline (3). The latter was further reacted with different substituted 2-amino benzothiazole to afford 8-cyano - 15, 16 –diimino benzothiazolo [2, 3-b] pyrimido [5, 6-e] pyrimido [3, 2-a] quinoline derivatives (4a-g). All these synthesized compounds were characterized by elemental analysis and spectral data. Keyward N,N’-Dimethyl formamide, Potassium carbonate, Pyrimido benzothiazole. INTRODUCTION Numerous quinolines, pyrimidines and pyrimido-quinoline derivatives have been prepared and their pharmacologically potent pyrimido [4,5-b] quino- lines have significant therapeutic importance 1-2 . Many of these compounds have proved to be active anticancers 3-4 , anti-inflammatories 5 , antiallergics 6 and antimicrobials 7-10 . Further, the utility of quinoline derivatives in the preparation of some dyes and pigments has been reported 11 . The most suitable protocol for the synthesis of functionalized organic com- pounds would be a one pot reaction due to the fact that the synthesis can performed without the isolation of the intermediates, without discharging any functional groups in short reaction time. Hence in present investigation, we report synthesis of 3, 11-dicyano-4-imino-2-methylthio -4H-pyrimido [1, 2-a] quinoline and diimino benzothiazolo pyrimido pyrimido quinolines nucleus which have also been recognized as promising antimicrobial activity. MATERIALS AND METHODS Experimental Section Melting points were determined by in an open capillary method and are uncorrected. The chemicals and solvents used for laboratory grade and were purified. IR spectra were recorded (in KBr pallets) on Shimadzu spectropho- tometer. 1 H NMR spectra were recorded (in DMSO-d 6 ) on Avance-300 MHz spectrometer using TMS as an internal standard. The mass were recorded on EI-Shimadzu GC–MS spectrometer. Elemental analyses were performed on a Heraeus CHN-O rapid analyzer. 3, 11-Dicyano-4-imino-2-methylthio - 4H-pyrimido [1, 2- a] quinoline ( 3) A mixture of 2-anino-3-cyano-quinoline 1 (2.91g, 0.01 m mol) and bis (methylthio) methylene malononitrile 2 (1.70 g, 0.01 m mol) was refluxed in the presence of N,N’-dimethyl formamide catalytic amount of anhydrous Potassium carbonate for 4 hrs. The reaction mixture was cooled to room temperature and poured in to ice cold water. The separated solid was filtered, washed with water and recrystallized from N,N’ –dimethyl formamide-etha- nol mixture to afford compound 3. Brown powder, ( 88% yield), Mp: above 300 o C; EI-MS (m/z-RA%) : 291 8-Cyano-15,16-diimino-3( H)-benzothiazolo[2,3- b] pyrimido[5,6- e]pyrimido[3,2-a] quinoline (4a) Brown powder, (86% yield), Mp: 324-328 o C; IR (cm -1 ,KBr) : 3221 (=NH); 3212 (=NH); 1 H NMR(DMSO-d 6 ,ppm): 6.3-7.0 (m,7H,Ar-H), 7.7 (s,1H, 8-Cyano-15,16-diiminobenzothiazolo[2,3-b] pyrimido[5,6 e]pyrimido [3,2-a] quinoline and its1, 3,4, -substituted derivatives (4a-g). A mixture of 3 (0.01m mol) and independently with 2-amino 6H- benzothiazole,2-amino 6-methyl benzothiazole,2-amino 4,6 dimethyl benzothiazole,2-amino 6- methoxy benzothiazole, 2-amino 6-chloro benzothiazole, 2-amino 6-nitro benzothiazole, 2- amino 6-chloro, 7-floro benzothiazole, 2-amino 7,6 dimethyl benzothiazole (0. 01m mol) in N,N’- dimethyl formamide catalytic amount of anhydrous Potassium carbonate was refluxed for 4 hrs. The reaction mixture was cooled to room temperature and poured in to ice cold water. The separated solid product was filtered, washed with water and recrystallized from N, N’- dimethyl formamide- ethanol mixture to give pure 4a-g. : 2.4 (s, 3H, SCH 3 ), 6.3-7.8 (m, 5H, Ar-H), 8.8(s,1H,=NH), 13 C NMR (300 MHz, DMSO-d 6 , ppm) 15,80,96, 110,115.9, 115.9, 116.2, 118.7, 124.7,124.9,127.2,128.7,139.2,156.7,164.9 ; Anal. Calcd. For: C 15 H 9 N 5 S; C, 61.84; H, 3.11; N, 24.04; Found: C, 61.38; H, 2.83; N, 23.62. (M + ) ,IR (cm -1 , KBr) : 3236 (=NH), 2216(CN), 1 H NMR (DMSO-d 6, ppm) 8-Cyano-15,16-diimino-1,3-(Dimethyl)-benzothiazolo[2,3-b]pyrimido [5,6-e]pyrimido[3,2-a] quinoline (4c) Brown powder, (88% yield), Mp: 322-326 o C; IR (cm -1 ,KBr): 3241 (=NH); 3226 (=NH); 1 H NMR (DMSO-d 6 , ppm): 2.3-2.6 (s,6H,Ar-CH 3 ), 6.2-7.0 (m,6H,Ar-H), 8.4 (s,1H, CH=C quin.,); 8.5 (s,2H,=NH).EI-MS (m/z-RA%): 8-Cyano-15,16-diimino-3-(methyl)-benzothiazolo[2,3-b]pyrimido[5,6- e]pyrimido[3,2-a] quinoline (4b) Brown powder, (85% yield), Mp: above 300 o C; IR (cm -1 , KBr) : 3238 (=NH); 3216 (=NH), 1 H NMR (DMSO-d 6 ,ppm): 2.5 (s,3H,Ar-CH 3 ), 6.1- 7.1 (m,7H,Ar-H,),7.6 (s,1H, CH=C quin.,);8.9 (s,2H,=NH). EI-MS (m/z- RA%): 408 (M+1) ; Anal. Calcd. C 22 H 13 N 7 S; C, 64.85; H, 3.22; N, 24.06; Found:C,64.23; H, 2.62; N, 23.56. CH=C quin.,) ; 9.2 (s,2H,=NH), EI-MS (m/z-RA%): 393 (M + ); Anal. Calcd. C 21 H 11 N 7 S; C, 64.11; H, 2.82; N, 24.92; Found: C,63.56; H, 2.36; N, 23.47.