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To a magnetically stirred 5 mL flask
containing o-pheny-lenediamine (0.11
g, 1 mmol) and CH2Cl2 (2 mL as solvent) was
added phenyl isothiocyanate (0.14 g, 1 mmol). After 15 min, methyl
acetylenedicarboxylate (0.08 g, 1 mmol) in toluene (5 mL) was added
to the reaction mixture and stirring continued under reflux. After
completion of the reaction (ca. 10 h; monitoring by TLC based on
the presence of intermediate 5), the solvent
was removed under reduced pressure, and the residue was washed with
cold toluene, Et2O, and EtOAc and crystallized from CH2Cl2.
Compound 4a: yield 0.19 g (70%); white
powder; mp 220 ˚C (dec.). IR (KBr): 1685 (C=N),
1663 (C=N), 1638 (C=C), 1589 and 1527 and 1473
and (C=C Ar). ¹H NMR (500.13 MHz, CDCl3): δH = 6.32
(1 H, d, ³
J
H,H = 7.7
Hz, SCHCH), 7.31 (1 H, t, ³
J
H,H = 7.5,
CH of Ar), 7.35 (1 H, t, ³
J
H,H = 7.2
Hz, CH of Ar), 7.44 (2 H, d, ³
J
H,H = 7.6
Hz, 2 CH of Ar), 7.52 (1 H, t, ³
J
H,H = 7.4
Hz, CH of Ar), 7.55 (1 H, d, ³
J
H,H = 7.8
Hz, CH of Ar), 7.60 (2 H, t, ³
J
H,H = 7.5
Hz, 2 CH of Ar), 7.66 (1 H, d, ³
J
H,H = 7.9
Hz, CH of Ar), 8.17 (1 H, d, ³
J
H,H = 7.7
Hz, SCHCH). ¹³C
NMR (125.75 MHz, CDCl3): δC = 106.01
(SCH=CH), 108.49 (CH of Ar),
119.62 (CH of Ar), 122.18 (CH of Ar), 124.90 (CH of Ar), 128.22
(2 CH of Ar), 129.17 (C
ipso
of
Ar), 129.47 (CH of Ar), 129.86 (2 CH of Ar), 132.52 (SCHCH), 134.74 (CH=CHC), 142.41 (C
ipso
of
Ar), 148 (C
ipso
of Ar), 160.38
(N=CS). MS: m/z (%) = 279 (7) [M+ + 2],
277 (6) [M+], 260 (100), 250
(10), 207 (9), 185 (9), 167 (18), 149 (49), 130 (16), 118 (9), 105
(92), 91 (55), 77 (90), 57 (48). 43 (53). Anal. Calcd for C16H11N3S (277.34):
C, 69.29; H, 4; N, 15.15. Found: C, 69.32; H, 4.2; N, 15.13.
Compunds 4e and 4e′:
yield 0.20 g (67%); white powder; mp 230 ˚C
(dec.). IR (KBr): 1676 (2 C=N), 1635 (2 C=N),
1591 (2 C=C), 1533 and 1509 and 1464 and (Ar). ¹H
NMR (500.13 MHz, CDCl3): δH = 2.43
(6 H, s, 2 Me), 2.45 (3 H, s, Me), 2.51 (3 H, s, Me), 6.27 (1 H,
d, ³
J
H,H = 7.7,
SCHCH), 6.28 (1 H, d, ³
J
H,H = 7.8
Hz, SCHCH), 7.11 (1 H, d, ³
J
H,H = 7.9
Hz, CH of Ar), 7.15 (1 H, d,³
J
H,H = 8.2
Hz, CH of Ar), 7.32 (4 H, d, ³
J
H,H = 7.3,
4 CH of Ar), 7.34 (1 H, s, CH of Ar), 7.38 (4 H, d,³
J
H,H = 8.1
Hz, 4 CH of Ar), 7.41 (1 H, d, ³
J
H,H = 8.2
Hz, CH of Ar), 7.45 (1 H, s, CH of Ar), 7.54 (1 H, d, ³
J
H,H = 8.2
Hz, CH of Ar), 8.11 (1 H, d, ³
J
H,H = 7.7Hz, SCHCH), 8.12 (1 H, d, ³
J
H,H = 7.8
Hz, SCHCH). ¹³C
NMR (125.7 MHz, CDCl3): δC = 21.37
(2 Me), 21.71 (Me), 21.75 (Me), 105.62, and 105.79 (2 SCH=CH), 108.01 and 108.59 (2 CH of Ar),
119.17 and 119.65 (2 CH of Ar), 123.28 (2 CH of Ar), 126.14 (2 CH
of Ar), 127.20 (C
ipso
of Ar),
127.87 (2 CH of Ar), 128.90 (C
ipso
of
Ar), 129.30 (C
ipso
of Ar),
130.10 (C
ipso
of Ar), 130.60
(2 CH of Ar), 132.16 and 132.23 (2 CH of Ar), 132.40 and 132.53
(2 SCHCH), 134.83 (2 CH=CHC), 139.43 (2 C
ipso
of
Ar), 140.37 and 142.41 (2 C
ipso
of
Ar), 148.04 (2 C
ipso
of Ar),
160.38 (2 N=CS). MS: m/z (%) = 290
(22), 289 (100), 274 (6), 260 (10), 246 (6), 224 (4), 208 (2), 167
(16), 149 (42), 129 (5), 111 (7), 97 (13), 83 (15), 57 (23), 43
(17). Anal. Calcd for C18H15N3S
(305. 40): C, 70.79; H, 4.95; N, 13.76. Found: C, 70.77; H, 4.97;
N, 13.74.
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King FD.
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2007,
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James SL.
Martin WP.
Smith TAD.
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2001,
42:
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