Table 1: Characterization data of m-(aralkyl amido/imidoalkyl) benzoic acids 1, m-(aralkyl amido/imidoalkyl) benzoic acid hydrazides 3, 4-amino-5-mercapto-3-[(3-aralkyl amido/imidoalkyl) phenyl]-1,2,4-triazoles 5, and 5-[(3-aralkyl amido/imidoalkyl) phenyl]-1,2,4-triazolo-[3,4-b]1,3,4-thiadiazines 6.

Compound RR1m.p. (°C)Yield (%) Calculated. (found) IR (KBr, cm−1)Mass (FAB+) (m/z)  ( M + + 1 ) 1H NMR (CDCl3, δ)
CHN

1aPhthalimidoH237–2396068.32 (68.30)3.94 (3.97)4.98 (4.95)3540 (OH), 1700 (C=O acid), 1665 (C=O amide)2827.26–8.11 (m, ar-H, 8H), 4.21
(s, NCH2, 2H), 11.2 (s, OH, 1H)

1bPhthalimido methylH100–1025069.15 (69.12)4.44 (4.46)4.74 (4.70)3543 (OH), 1720 (C=O acid), 1665 (C=O amide)2967.25–8.21 (m, ar-H, 8H), 4.21 (m, NCH2, 2H), 3.91 (m, ar-CH2, 2H), 11.4 (s, OH, 1H)

1c2-Phenyl-3-methyl-quinazolin (3H)4-oneH130–1325574.58 (74.54)4.90 (4.93)7.56 (7.54)3530 (OH), 1695 (C=O acid), 1685 (C=O quinazolone moiety), 1665 (C=O amide), 1642 (C=N)3717.12–8.25 (m, ar-H, 13H), 4.23 (m, NCH2, 2H), 3.94 (m, ar-CH2, 2H), 11.2 (s, OH, 1H)

1dNicotinamidoC6H5118-1196572.28 (72.25)4.85 (4.88)8.43 (8.42)3540 (OH), 3390 (NH), 1700 (C=O acid), 1656 (C=O amide), 1656 (C=N)3337.12–8.17 (m, ar-H, 13H), 8.15 (brs, CONH, 1H), 5.56 (s, CH, 1H), 11.0 (s, OH, 1H)

3aPhthalimidoH178–1805565.08 (65.03)4.44 (4.48)14.23 (14.20)3316 (NH), 1665 (C=O amide)29610.43 (s, NH, 1H), 7.20 (brs, NH2, 2H), 7.28–8.25 (m, ar-H, 8H), 4.21 (s, NCH2, 2H),

3bPhthalimido methylH162–1645066.01 (66.00)4.89 (4.91)13.58 (13.53)3210 (NH), 1667 (C=O amide)31010.43 (s, NH, 1H), 7.20 (brs, NH2, 2H), 7.25–8.19 (m, ar-H, 8H), 4.26 (m, NCH2, 2H), 3.93 (m, ar-CH2, 2H).

3c2-Phenyl-3-methyl-quinazolin (3H)4-oneH114–1165571.86 (71.83)5.24 (5.28)14.57 (14.55)3286 (NH), 1685 (C=O quinazolone moiety), 1665 (C=O amide), 1642 (C=N)38510.52 (s, NH, 1H), 7.25 (brs, NH2, 2H), 7.42–8.29 (m, ar-H, 13H), 4.15 (m, NCH2, 2H), 3.91 (m, ar-CH2, 2H).

3dNicotinamidoC6H588–906069.35 (69.30)5.24 (5.27)16.17 (16.14)3390 (NH), 3310 (NH amido), 1669 (C=O amide), 1556 (C=N)34610.47 (s, NH, 1H), 7.23 (brs, NH2, 2H), 8.35 (brs, CONH, 1H), 7.27–8.27 (m, ar-H, 13H), 5.58 (s, CH, 1H).

5aPhthalimidoH298-2995058.11 (58.07)3.73 (3.77)19.93 (19.90)3390 (NH), 2568 (SH), 1660 (C=O amide), 1640 (C=N)35211.26 (s, SH, 1H), 7.15 (brs, NH2, 2H), 7.24–8.23 (m, ar-H, 8H), 4.21 (s, NCH2, 2H).

5bPhthalimido methylH208–2104559.16 (59.14)4.14 (4.16)19.17 (19.14)3389 (NH), 2560 (SH), 1668 (C=O amide), 1645 (C=N)36611.31 (s, SH, 1H), 7.21 (brs, NH2, 2H), 7.27–8.28 (m, ar-H, 8H), 4.24 (m, NCH2, 2H), 3.93 (m, ar-CH2, 2H).

5c2-Phenyl-3-methyl-quinazolin (3H)4-oneH146–1485565.44 (65.40)4.58 (4.61)19.08 (19.03)3396 (NH), 2565 (SH), 1685 (C=O quinazolone moiety), 1656 (C=O amide), 1642 (C=N)44111.43 (s, SH, 1H), 7.27 (brs, NH2, 2H), 7.33–8.25 (m, ar-H, 13H), 4.18 (m, NCH2, 2H), 3.96 (m, ar-CH2, 2H).

5dNicotinamidoC6H5192–1946062.67 (62.63)4.51 (4.55)20.88 (20.85)3396 (NH), 3315 (NH amido), 2568 (SH), 1665 (C=O amide), 1642 (C=N)40311.41 (s, SH, 1H), 7.22 (brs, NH2, 2H), 7.18–8.23 (m, ar-H, 13H), 8.31 (brs, CONH, 1H), 5.54 (s, CH, 1H).

6aPhthalimidoH284-2856270.57 (70.53)4.01 (4.05)13.27 (13.24)3350 (NH), 1663 (C=O amide), 1585 (C=N)52810.28 (brs, NH of thiadiazine, 1H), 6.91–8.23 (m, ar-H, 18H), 4.22 (s, NCH2, 2H).

6bPhthalimido methylH>3004570.96 (70.92)4.28 (4.30)12.93 (12.90)3356 (NH), 1660 (C=O amide), 1595 (C=N)54210.26 (brs, NH of thiadiazine, 1H), 7.12–8.21 (m, ar-H, 18H), 4.21 (m, NCH2, 2H), 3.92 (m, ar-CH2, 2H).

6c2-Phenyl-3-methyl-quinazolin (3H)4-oneH75-765074.00 (73.97)4.58 (4.61)13.63 (13.61)3360 (NH), 1680 (C=O quinazolone moiety), 1650 (C=O amide), 1585 (C=N)61710.24 (brs, NH of thiadiazine, 6.99–8.19 (m, ar-H, 23H), 4.28 (m, NCH2, 2H), 3.99 (m, ar-CH2, 2H).

6dNicotinamidoC6H5298-2995772.64 (72.61)4.53 (4.57)14.52 (14.50)3396 (NH), 1616 (C=O amide), 1556 (C=N)57910.29 (brs, NH of thiadiazine, 1H), 7.20–7.88 (m, ar-H, 23H), 8.15 (brs, CONH, 1H), 5.57 (s, CH, 1H).