10.07.2015 Views

Download (4Mb) - Etheses - Saurashtra University

Download (4Mb) - Etheses - Saurashtra University

Download (4Mb) - Etheses - Saurashtra University

SHOW MORE
SHOW LESS

You also want an ePaper? Increase the reach of your titles

YUMPU automatically turns print PDFs into web optimized ePapers that Google loves.

Part-IIExperimentalwere reacted under microwave irradiation (55 min) as per procedure described for thecompound Vi. The crude product on recrystallization from methanol-chloroform mixtureyielded 2-(2-chloroethyl)-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one(Vxxii).M.P. : 156-158 o C (156-158 o C) 9 ; Yield: 83%Mol. Formula : C 12 H 13 ClN 2 OS; Mol. Wt. 268.76IR (KBr) cm -1 : 2935(γ C-H ), 1665(γ CONH ), 665(γ C-Cl ).1 H NMR (CDCl 3 )δppm : 1.90 (4H, s, CH 2 at 6 and 7), 2.81 (2H, s, CH 2 at 5), 3.02 (2H, s,CH 2 at 8), 3.23 (2H, t, CH 2 , J = 7.0), 4.02 (2H, t, CH 2 , J = 7.2),11.90 (1H, s, br, NH)23. Synthesis of 2-(2-chloroethyl)quinazolin-4(3H)-one (Vxxiii)A mixture of methylanthranilate (3.2 gm; 0.02 mole), acrylonitrile (1.21 gm; 0.022 mole)and catalytic amount of HCl (0.5 ml) were reacted under microwave irradiation (40 min)as per procedure described for the compound Vi. The crude product on recrystallizationfrom methanol-chloroform mixture yielded 2-(2-chloroethyl)quinazolin-4(3H)-one(Vxxiii).M.P. : 200-202 o C; Yield: 91%Mol. Formula : C 10 H 9 ClN 2 O; Mol. Wt. 208.64IR (KBr) cm -1 : 2979(γ C-H ), 1665(γ CONH ), 771(γ C-Cl ).1 H NMR (CDCl 3 )δppm : 3.18 (2H, t, CH 2 , J = 6.3, 7.2), 4.06 (2H, t, CH 2 at 2, J = 6.3,7.2), 7.44-8.07 (4H, m, Ar-H ).24. Synthesis of 2-(2-chloroethyl)-9-methoxy-3H-benzo[4,5]thieno[3,2-d]pyrimidin-4-one (Vxxiv)A mixture of methyl 3-amino-4-methoxybenzo[b]thiophene-2-carboxylate (Ixvi, 4.7 gm;0.02 mole), acrylonitrile (1.21 gm; 0.022 mole) and catalytic amount of HCl (0.5 ml)were reacted under microwave irradiation (75 min) as per procedure described for thecompound Vi. The crude product on recrystallization from methanol-chloroform mixtureyielded 2-(2-chloro-ethyl)-9-methoxy-3H-benzo[4,5]thieno[3,2-d]pyrimidin-4-one(Vxxiv).372

Hooray! Your file is uploaded and ready to be published.

Saved successfully!

Ooh no, something went wrong!