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Avinash Patil et al
yield a precipitate which was filtered and recrystal- (KBr/cm–1): 1635 (C=C), 1678 (C=O), 2920 (C–H
lized from ethanol and shows m.p.: 240–242°C in alkyl), 1642 (C=N), 1410 (C–N), 3320 (N–H), 716
68% yield.
Rf = 0⋅79; IR:(KBr/cm–1): 1514 (C=C), 1714
(C–S–C), 1021 (S=O), 1480 (N=N).
1H NMR (300 MHz, CDCI3) δppm: 12⋅2 (s, 1H, NH
(C=O), 2980 (C–H alkyl), 3126 (C–H Ar), 1467 benz), 12⋅5 (s, 1H, NH tetrazole), 5⋅3 (s, 2H,
(C=N), 1543 (C–N), 3153 (N–H), 740 (C–S–C), CH2SO), 6⋅9–8⋅5 (m, 8H, ArH). MS (m/z) 392[M]+;
1033 (S=O) 1261 (C–O–C).
Anal. Calcd. for C17H12N8O2S1: C, 52⋅04; H, 3⋅06;
1H NMR (300 MHz,CDCI3) δppm: 3.9 (s, 6H, N, 28⋅57. Found: C, 52⋅32; H, 3⋅31; N, 28⋅68.
OCH3), 5⋅0 (s, 2H, CH2SO), 12⋅4 (s,1H, NH), 6⋅4–
8⋅0 (m, 11H, ArH). MS (m/z) 460[M]+; Anal. Calcd. 2.2f 2-((5-Methoxy benzo[d]imidazol-2-ylsulfinyl)
for C24H20N4O4S1: C, 62⋅60; H, 4⋅34; N, 12⋅17. methyl)-3-(3,4 dimethoxy phenyl) quinazolin-4(3H)-
Found: C, 62⋅80; H, 4⋅61; N, 12⋅07. Compounds 5b– one (5f): Yield: 0⋅66g (64%); m.p.: 236–238°C;
o were obtained similarly.
Rf: 0⋅78, IR (KBr/cm–1): 1521 (C=C), 1710 (C=O),
2950 (C–H alkyl), 1610 (C=N), 1467 (C–N), 3190
2.2b 2-((1-H Benzo[d] imidazol-2-yl sulfinyl) (N–H), 780 (C–S–C), 1265 (C–O–C), 1049 (S=O).
methyl)-3-(pyridyl-2-yl) quinazolin-4(3H)- one (5b):
1H NMR (300 MHz, CDCI3) δppm: 3⋅8 (s, 9H,
Yield: 0⋅64 g (62%); m.p.: 252–254°C; Rf: 0⋅80, IR OCH3), 12⋅0 (s, 1H, NH benz), 4⋅8 (s, 2H, CH2SO),
(KBr/cm–1): 1592 (C=C), 1680 (C=O), 2950 (C–H 6⋅6–7⋅8 (m, 8H, ArH). MS (m/z) 491 [M]+; Anal.
alkyl), 1668 (C=N), 1514 (C–N), 3180 (N–H), 785 Calcd. for C25H22N4O5S1: C, 61.09; H, 4⋅48; N,
(C–S–C), 1030 (S=O).
11⋅40. Found: C, 61⋅32; H, 4⋅51; N, 11⋅30.
1H NMR (300 MHz, CDCI3) δppm: 5⋅1 (s, 2H,
CH2SO), 11⋅8 (s, 1H, NH benz), 6⋅4–8⋅4 (m,12H,
ArH). MS (m/z) 401 [M]+; Anal. Calcd. for
C21H15N5O2S1: C, 62⋅84; H, 3⋅74; N, 17⋅45. Found:
C, 62⋅92; H, 3⋅91; N, 17⋅28.
2.2g 2-((5-Methoxy benzo[d]imidazol-2-yl sulfinyl)
methyl)-3-(pyridyl-2-yl) quinazolin-4(3H)-one (5g):
Yield: 0⋅69 g (67%); m.p.: 260–261°C, Rf: 0⋅78, IR
(KBr/cm–1): 1570 (C=C), 1692 (C=O), 2940 (C–H
alkyl), 1668 (C=N), 1514 (C–N), 3200 (N–H), 780
(C–S–C), 1265 (C–O–C), 1033 (S=O).
2.2c 2-((1-H
Benzo[d]imidazol-2-yl
sulfinyl)
1H NMR (300 MHz, CDCI3) δppm: 3⋅9 (s, 3H,
OCH3), 11⋅9 (s, 1H, NH benz), 5⋅0 (s, 2H, CH2SO),
6⋅5–8⋅5 (m, 8H, ArH). MS (m/z) 431 [M]+; Anal.
Calcd. for C22H17N5O3S1: C, 61⋅25; H, 3⋅94; N,
16⋅24. Found: C, 61⋅52; H, 4⋅21; N, 16⋅38.
methyl)-3-(pyridyl-3-yl) quinazolin-4(3H)-one (5c):
Yield: 0⋅74 g (72%); m.p.: 240–242°C, Rf: 0⋅81, IR
(KBr/cm–1): 1585 (C=C), 1670 (C=O), 2945 (C–H
alkyl), 1660 (C=N), 1524 (C–N), 3210 (N–H), 782
(C–S–C), 1030 (S=O).
1H NMR(300 MHz,CDCI3) δppm: 4⋅9 (s, 2H,
CH2SO), 11⋅8 (s,1H, NH benz), 6⋅4–8⋅2 (m, 12H,
ArH). MS (m/z) 401 [M]+; Anal. Calcd. for
C21H15N5O2S1: C, 62⋅84; H, 3⋅74; N, 17⋅45. Found:
C, 62⋅72; H, 4⋅04; N, 17⋅38.
2.2h 2-((5-Methoxy benzo[d]imidazol-2-yl sulfinyl)
methyl)-3-(pyridyl-3-yl) quinazolin-4(3H)-one (5h):
Yield: 0⋅66 g (65%); m.p.: 228–230°C, Rf: 0⋅82, IR
(KBr/cm–1): 1580 (C=C), 1670 (C=O), 2952 (C–H
alkyl), 1660 (C=N), 1524 (C–N), 3210 (N–H), 782
(C–S–C), 1270 (C–O–C), 1033 (S=O).
2.2d 2-((1-H
Benzo[d]imidazol-2-yl
sulfinyl)
methyl)-3-(pyrazine-2-yl) quinazolin-4(3H)-one (5d):
Yield: 0⋅72 g (70%); m.p.: 292–294°C, Rf: 0⋅82, IR
(KBr/cm–1): 1632 (C=C), 1700 (C=O), 2940 (C–H
alkyl), 1642 (C=N), 1468 (C–N), 3250 (N–H), 742
(C–S–C), 1029 (S=O). 1H NMR (300 MHz, CDCI3)
δppm: 4⋅9 (s, 2H, CH2SO); 11⋅8 (s, 2H, NH), 6⋅4–8⋅0
(m, 12H, ArH). MS (m/z) 402 [M]+; Anal. Calcd. for
C20H14N6O2S1: C, 59⋅70; H, 3⋅48; N, 20⋅89. Found:
C,59⋅92; H, 3⋅78; N, 21⋅20.
1H NMR (300 MHz, CDCI3) δppm: 5⋅0 (s, 2H,
CH2SO), 3⋅9 (s, 3H, OCH3), 12⋅3 (s, 1H, NH benz),
6⋅6–7⋅4 (m, 8H, ArH). MS (m/z) 431 [M]+; Anal.
Calcd. for C22H17N5O3S1: C, 61⋅25; H, 3⋅94; N,
16⋅24. Found: C, 61⋅52; H, 4⋅31; N, 16–38.
2.2i 2-((5-Methoxy benzo[d]imidazol-2-yl sulfinyl)
methyl)-3-(pyrazine-2-yl) quinazolin-4(3H)-one (5i):
Yield: 0⋅74g (72%); m.p.: 286–288°C, Rf: 0⋅84, IR
(KBr/cm–1): 1644 (C=C), 1705 (C=O), 2932 (C–H
alkyl), 1652 (C=N), 1468 (C–N), 3240 (N–H), 742
(C–S–C), 1042 (S=O), 1272 (C–O–C).
2.2e 2-((1-H Benzo[d]imidazol-2-yl sulfinyl) methyl)-
3-(tetrazole-5-yl) quinazolin-4(3H)-one (5e): Yield:
056 g (54%); m.p.: above 300°C; Rf: 0⋅70, IR