(%) for [C.sub.30] [H.sub.30] [N.sub.2] O: (Mol. Wt. = 434) C, 82.91; H, 6.96; N, 6.45.
(%) for [C.sub.27] [H.sup.24] [N.sup.2] O: (Mol. Wt. = 392) C, 82.62; H, 6.16; N, 7.14.
(%) for [C.sub.27] [H.sub.28] Cl[N.sub.2] O: (Mol. Wt. = 426) C, 75.96; H, 5.46; N, 6.56.
(%) for [C.sub.28] [H.sub.26] [N.sub.2] O: (Mol. Wt. = 406) C, 82.73; H, 6.45; N, 6.89.
formula: C 17 H 13 ClN 4 O 3 S;
Mol. Wt.: 388; IR (KBr, v max /cm -1 ): 3065 (Ar C-H), 1677 (C=N), 1616 (Ar C=C), 1249 (C-O-C), 684 (C- Cl), 621 (C-S); 1 H-NMR (600 MHz, DMSO, d/ppm): 11.75 (s, 1H, CONH), 8.34 (s, 1H, H-7'''), 7.97 (d, J = 7.8 Hz, 1H, H-6'), 7.92 (d, J = 7.8 Hz, 1H, H-6'''), 7.71 (d, J = 8.4 Hz, 1H, H-3'), 7.62 (t, J = 8.4 Hz, 1H, H-5'), 7.59 (t, J = 7.8 Hz, 1H, H-4'), 7.54 (dd, J = 7.8, 1.8 Hz, 1H, H-3'''), 7.23 (dt, J = 7.8, 1.8 Hz, 1H, H-4'''), 6.90 (dt, J = 7.2, 1.8 Hz, 1H, H-5'''), 4.67 (s, 2H, H-2''); EIMS (m/z): 390 [M+2] + , 388 [M] + , 253 [C 10 H 6 ClN 2 O 2 S] + , 225 [C 9 H 6 ClN 2 OS] + , 212 [C 8 H 5 ClN 2 OS] + , 179 [C 8 H 4 ClN 2 O] + , 163 [C 8 H 7 N 2 O 2 ] + , 153 [C 7 H 4 ClNO] + , 139 [C 7 H 4 ClO] + , 137 [C 7 H 4 ClN] + , 135 [C 7 H 7 N 2 O] + ,
6'-(4-Nitrophenyl)-3'-(thiazol-2-yl)-4'-thioxo-3'-4'-dihydrospiro[indoline-3,2'-[1,3,5]-oxadiazin]-2-one (5h): [C.sub.19][H.sub.11][N.sub.5][O.sub.4][S.sub.2];
Mol. wt.: 437.45; Yield: 68%; M.P.: 253-254[degrees]C, IR (KBr): 1693 [cm.sup.-1] (C=O of isatin), 1567 [cm.sup.-1] (C=N of thiazole), 696 [cm.sup.-1] (C-S-C of thiazole), 1168 [cm.sup.-1] (C=S), 1550-1570 [cm.sup.-1]of (N=O of N[O.sub.2]).
For.: C18H16ClN3O2S; Mol. Wt.: 373.8; IR (KBr, cm-1) vmax: 3315 (N-H stretching), 3065 (C- H of aromatic ring), 1663 (C=N of Oxadiazole ring),1653 (C=O), 1559 (C=C aromatic), 1289 (C-O-C bond), 687 (C-Cl bond), 635 (C-S bond); 1H-NMR (400 MHz, CDCl3, d / ppm): 8.95 (s, 1H, -NH), 7.91 (d, J = 8.4 Hz, 2H, H-3' and H-5'), 7.47 (d, J = 8.4 Hz,2H, H-2' and H-6'), 7.15 (s, 2H, H-2''' and H-6'''), 6.73 (s,
For.: C17H14ClN3O2S; Mol. Wt.: 359.8; IR (KBr, cm-1) vmax: 3323 (N-H stretching), 3035 (C- H of aromatic ring), 1633 (C=N of Oxadiazole ring),1613 (C=O), 1523 (C=C aromatic), 1231 (C-O-C bond), 677 (C-Cl bond), 619 (C-S bond); 1H-NMR (400 MHz, CDCl3, d / ppm): 10.32 (s, 1H, -NH), 7.92 (d, J = 8.4 Hz, 2H, H-3' and H-5'), 7.46 (d, J = 8.1 Hz,2H, H-2' and H-6'), 7.39 (d, J = 7.6 Hz, 1H, H-6"'),7.24 (d, J = 7.6 Hz, 1H, H-3"'), 7.14 (br.t, J = 7.6, 1.2Hz, 1H, H-5"'), 7.11 (dt, J = 6.6, 1.0 Hz, 1H, H-4"'),4.31 (s, 2H, CH2-2''), 3.30 (s, 3H, CH3-2'''); EIMS (m/z): 361 (4%) [M+2]+, 359 (12%) [M+], 253 (17%),137 (95%), 111 (35%), 106 (67%), 91 (71%), 77 (21%), 51 (100%).
For.: C17H14ClN3O2S; Mol. Wt.: 359.8; IR (KBr, cm-1) vmax: 3343 (N-H stretching), 3065 (C- H of aromatic ring), 1671 (C=N of Oxadiazole ring),1667 (C=O), 1567 (C=C aromatic), 1280 (C-O-C bond), 676 (C-Cl bond), 631 (C-S bond ); 1H-NMR (400 MHz, CDCl3, d / ppm): 9.04 (s, 1H, -NH), 7.92 (d, J = 8.4 Hz, 2H, H-3' and H-5'), 7.47 (d, J = 8.4 Hz,2H, H-2' and H-6'), 7.36 (s, 1H, H-2'''), 7.31 (d, J = 8.0Hz, 1H, H-6'''), 7.17 (t, J = 8.0 Hz, 1H, H-5'''), 6.89 (d, J = 7.2 Hz, 1H, H-4'''), 4.00 (s, 2H, CH2-2''), 2.31 (s, 3H, CH3-3'''); EIMS (m/z): 361 (5%) [M+2]+, 359(15%) [M+], 253 (16%), 137 (97%), 111 (37%), 106(62%), 91 (69%), 77 (29%), 51 (100%).
4-[2-{(2-Bromoethyl)thiol}-1,3,4-Oxadiazol-5-yl]-1- (phenylsulfonyl)piperidine (4c): Mustard viscous liquid; Yield 77%; Molecular formula: C 15 H 18 BrN 3 O 3 S 2 ; Mol. Wt. 432; IR (KBr, cm -1 ) v max : 3035, 1577, 1631, 1328; 1 H- NMR (300 MHz, CDCl 3 Delta / ppm): 7.77 (dd, J = 6.9,1.8 Hz, 2H, H-2", 6"), 7.58-7.55 (m, 3H, H-3" to 5"), 3.71 (t, J = 2.1 Hz, 2H, H-2"'), 3.60 (t, J = 2.1 Hz, 2H, H-1"'), 2.89 (t, J = 2.1 Hz, 2H, H eq -2' and 6'), 2.63 (t, J = 2.1 Hz, 2H, H ax -2' and 6'), 2.13-1.99 (m, 1H, H-4'), 1.95-1.90 (m, 4H, H-3', 5'); EIMS m/z (%): 432 (M + , 6), 252 (11), 224 (12), 107 (100), 156 (59), 141 (21), 77 (22).
4-[2-(Propylthio)-1,3,4-Oxadiazol-5-yl]-1- (phenylsulfonyl)piperidine (4d): White granules; Yield 78%; m.p: 168-170; Molecular formula: C 16 H 21 N 3 O 3 S 2 ; Mol. Wt. 367; IR (KBr, cm -1 ) v max : 3028, 2920, 1579, 1620, 1330; 1 H- NMR (300 MHz, CDCl 3 Delta / ppm): 7.76 (dd, J = 7.8, 1.8 Hz, 2H, H-2", 6"), 7.62-7.49 (m, 3H, H-3" to 5"), 3.67 (t, J = 3.9 Hz, 2H, H eq -2' and 6'), 3.64 (t, J = 3.9 Hz, 2H, H ax -2' and 6'), 3.10 (t, J = 2.5 Hz, 2H, H-1"'), 2.13-2.00 (m, 1H, H-4'), 1.98-1.96 (m, 4H, H-3', 5'), 1.41 (sex, J = 5.7 Hz, 2H, H-2"'), 0.90 (t, J = 2.0 Hz, 3H, H-3"'); EIMS m/z (%): 367 (M + , 8), 252 (45), 224 (40), 156 (100), 141 (11), 77 (21), 41 (31); Anal.
4-[2-(Isopropylthio)-1,3,4-Oxadiazol-5-yl]-1- (phenylsulfonyl)piperidine (4e): Light yellow crystals; Yield 73%; m.p: 106- 108; Molecular formula: C 16 H 21 N 3 O 3 S 2 ; Mol. Wt. 367; IR (KBr, cm -1 ) v max : 3026, 2887, 1575, 1623, 1327; 1 H-NMR (300 MHz, CDCl 3 Delta / ppm): 7.76 (dd, J = 7.8, 1.8 Hz, 2H, H-2", 6"), 7.61-7.58 (m, 3H, H- 3" to 5"), 3.67 (t, J = 3.9 Hz, 2H, H eq -2' and 6'), 3.64 (t, J = 3.9 Hz, 2H, H ax -2' and 6'), 2.88-2.85 (m, 1H, H- 1"'), 2.11-1.98 (m, 1H, H-4'), 1.95-1.92 (m, 4H, H-3', 5'), 1.21 (s, 6H, H-2"', 3"'); EIMS m/z (%): 367 (M + , 12), 252 (35), 224 (30), 156 (40), 141 (14), 77 (31), 41(100); Anal.