REACTIONS OF PYRROLE-1- AND PYRROLE-2-CARBODITHIOATES
551
a described under compound IIIa from 1.2 g %: C 65.84; H 5.35; N 4.56; S 19.85. C18H17NOS2.
(10 mmol) of 4,5,6,7-tetrahydroindole, 0.56 g Calculated, %: C 66. 02; H 5.23; N 4.28; S
(10 mmol) of KOH, 1.52 g (20 mmol) of carbon 19.58.
disulfide, and 0.98 g (10 mmol) of acetylene IIa we
2-(1-Thioxo-3-phenyl-5,6,7,8-tetrahydro-1H-
obtained 0.48 g (42%) of orange crystals of a mixture
[1,3]-thiasolo[3,4-a]indol-3-yl)-1-(2-furyl)ethan-1-
of Z,Z-, E,E-, and Z,E-isomers of sulfide IVa.
one (VIIIe). Along procedure a described under
Along procedure c described under compound IIIa compound IIIa from 0.12 g (1 mmol) of 4,5,6,7-
from 1.2 g (10 mmol) of 4,5,6,7-tetrahydroindole, tetrahydroindole, 0.06 g (1 mmol) of KOH, 0.15 g
0.56 g (10 mmol) of KOH, 1.52 g (20 mmol) of (2 mmol) of carbon disulfide, and 0.20 g (1 mmol) of
carbon disulfide, 0.98 g (10 mmol) of acetylene IIa,
and 1 ml of acetic acid we obtained 0.1 g (9%) of mp 158 159 C. IR spectrum, , cm : 553, 578,
acetylene was obtained 0.18 g (46%) of pyrrole VIIIe,
1
sulfide IVa and 1.5 g (51%) of pyrrole VIIa, mp 592, 630, 665, 694, 711, 762, 812, 825, 882, 903,
118 C.
953, 978, 1015, 1033, 1049, 1084, 1144, 1184,
1214, 1260, 1306, 1363, 1386, 1448, 1465, 1547,
1567, 1632, 1671, 2851, 2922, 3025, 3059, 3122.
1H NMR spectrum (CDCl3, , ppm): 1.82 m (4H,
1
IR spectrum, , cm : 561, 685, 717, 797, 809,
830, 850, 925, 959, 982, 1038, 1148, 1169, 1187,
1216, 1261, 1307, 1330, 1344, 1364, 1425, 1448,
1463, 1520, 1553, 1583, 1694, 1703, 2849, 2922,
C
5,6H2), 2.63 m (4H, C4,7H2), 3.89, 4.2 d.d (2H,
CH2CO), 6.59 d.d (1H, H4 of furan ring), 6.75 s
(1H, H3), 7.18 d.d (1H, H3 of furan ring), 7.29 m
(3H, H arom), 7.35 m (2H, H arom), 7.59 d.d (1H,
H5 of furan ring). Found, %: C 66.84; H 5.35; N
3.96; S 16.85. C22H19NO2S2. Calculated, %: C
67.15; H 4.87; N 3.56; S 16.30.
3059, 3729, 3314. 1H NMR spectrum (CDCl3,
,
ppm): 1.31 t (3H, CH3), 1.77 m (4H, C5,6H2),
2.55 m (4H, C4,7H2), 4.24 q (2H, CH2), 6.24 d.d
(1H,SCH=, J 10.8 Hz), 7.06 d (1H, H3), 8.63 d.d
(1H, CH= , J 10.8 Hz), 9.40 br.s (1H, NH).
Found, %: C 56.44; H 6.12; N 4.56; S 20.95.
C14H17NO2S2. Calculated, %: C 56.92; H 5.80;
N 4.74; S 21.71.
REFERENCES
1. Drozd, V.N., Petrov, M.L., Kuz,mina, N.Ya., and
Vyazgin, A.S., Usp. Khim., 1988, vol. 47, no. 1,
pp. 94 113.
2-Benzoylvinyl 4,5,6,7-tetrahydroindol-2-carbo-
dithioate (VIIb) and 2-(1-thioxo-5,6,7,8-tetra-
hydro-1H-[1,3]thiazolo[3,4-a]indol-3-yl)-1-phenyl-
ethanone (VIIIb). Along procedure c described
under compound IIIa from 0.12 g (1 mmol) of
4,5,6,7-tetrahydroindole, 0.06 g (1 mmol) of KOH,
0.15 g (2 mmol) of carbon disulfide, and 0.13 g
(1 mmol) of acetylene IIb was obtained 0.01 g of oily
substance containing pyrrole VIIb, and 0.15 g (47%)
of pyrrole VIIIb, mp 193 194 C.
2. Kuz,mina, N.Ya., Petrov, M.L., and Petrov, A.A.,
Zh. Org. Khim., 1984, vol. 20, no. 12, p. 2511.
3. Sobenina, L.N., Mikhaleva, A.I., Petrova, O.V.,
Toryashinova, D.S.D., and Trofimov, B.A., Zh. Org.
Khim., 1999, vol. 35, no. 10, pp. 1534 1537.
4. Drozd, V.N., Popova, O.A., Vyazgin, A.S., and
Dmitriev, D.B., Zh. Org. Khim., 1983, vol. 19, no. 4,
pp. 847 853.
1H NMR spectrum of pyrrole VIIb (CDCl3,
,
5. Trofimov, B.A. and Amosova, S.V., Divinilsul,fid i
ego proizvodnye (Divinylsulfide and Its Derivatives),
Novosibirsk: Nauka, 1983.
6 Japan Patent 71371, 1970; Ref. Zh. Khim., 1972,
5N 685.
ppm): 1.77 m (4H, C5,6H2), 2.55 m (4H, C4,7H2),
7.09 s (1H, H3), 7.25 d.d (1H, SCH=, J 9.3 Hz),
7.53 m (3H, H arom), 8.00 m (2H, H arom), 8.93
d.d (1H, COCH=, J 9.3 Hz). IR spectrum of pyrrole
1
VIIIb, , cm : 690, 740, 745, 766, 811, 827, 940,
7. Bax, A. and Subramamian, S., J. Magn. Reson.,
1986, vol. 67, no. 3, pp. 565 569.
8. Bax, A. and Summers, M.F., J. Am. Chem. Soc.,
1986, vol. 108, no. 8, pp. 2093 2094.
9. Wagner, G. and Wuthrich, K., J. Mol. Biol., 1982,
vol. 155, no. 3, pp. 347 349.
1046, 1113, 1141, 1159, 1184, 1261, 1224, 1245,
1305, 1332, 1338, 1401, 1450, 1470, 1498, 1542,
1
1579, 1595, 1673, 2851, 2928. H NMR spectrum of
pyrrole VIIIb (CDCl3, , ppm): 2.63 m (4H, C4,7H2),
1.82 m (4H, C5,6H2), 3.76 d.d (1H, CHCH2, J 10.3,
20 Hz), 3.98 d.d (1H, CHCH2, J 4.1, 20 Hz), 6.09
d.d (1H, CHCH2, J 4.1, 10.3 Hz), 6.73 s (1H, H3),
7.52 m (3H, H arom), 7.91 m (2H, H arom). Found,
10. Trofimov, B.A. and Mikhaleva, A.I., N-Vinilpirroly
(N-Vinylpyrrols), Novosibirsk: Nauka, 1984.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 37 No. 4 2001