K. Bourahla et al. / Tetrahedron Letters 48 (2007) 5785–5789
5789
1
1
1
1. Hu, B.; Molonas, M.; Ellingboe, J. Heterocycles 2002, 57,
57–870.
from AcOEt. Yellow needles, mp = 246–250 °C.
NMR (300 MHz, (CD SO) d: 6.13 (s, 2H, OCH
7.11 (m, 3H, J = 8.7 Hz, H-2, H-3, H-6, Ar); 7.54 (s, 1H,
H
8
3
)
2
2
O);
2. (a) Bazureau, J. P.; Mongin, F.; Hamelin, J.; Texier-
Boullet, F. In Microwave in Heterocyclic Chemistry, 2nd
ed.; Loupy, A., Ed.; Microwave in Organic Synthesis;
Wiley-VCH: Weinheim, Germany, 2006; pp 426–523,
Chapter 10; (b) Besson, T.; Brain, C. In Heterocyclic
Chemistry Using Microwave Assisted Approaches; Tierney,
J. P., Lidstr o¨ m, P., Eds.; Microwave Assisted Organic
Synthesis; Blackwell Publishing, 2004; Chapter 3.
1
3
@CH); 13.74 (br s, 1H, NH). C NMR (300 MHz,
0
(CD
3
)
2
SO) d: 102.1 (OCH
2
O); 109.2 (C-2 , Ar); 109.4 (C-
0
0
0
5 , Ar); 122.8 (C@CH, C-5); 126.6 (C-6 , Ar); 127.1 (C-1 ,
0
0
Ar); 131.8 (@CH); 148.2 (C-4 , Ar); 149.6 (C-3 , Ar); 169.3
(C-4, C@O); 195.3 (C-2, C@S). HRMS, m/z: 264.9864
+
found (calculated for C11
H
7
NO
3
S
2
, M requires 264.9867).
25. Sing, W. T.; Lee, C. L.; Yeo, S. L.; Lim, S. P.; Sim, M. M.
Bioorg. Med. Chem. Lett. 2001, 11, 91–94.
26. Yan, S.; Larson, G.; Wu, J. Z.; Appleby, T.; Ding, Y.;
Hamatake, R.; Hong, Z.; Yao, N. Bioorg. Med. Chem.
Lett. 2007, 17, 63–67.
1
3. (a) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A.
R. J. Comb. Chem. 2002, 4, 95; (b) Blackwell, H. E. Org.
Biomol. Chem. 2003, 1, 1251; (c) Krstenansky, J. L.;
Cotteril, I. Curr. Opin. Drug Discovery Dev. 2000, 3, 454;
(
6
d) Larhed, M.; Hallberg, A. Drug Discovery Today 2001,
, 406.
27. Gur’eva, R. F.; Savrin, S. B. Russ. Chem. Rev. 1998, 67,
209–224.
1
4. Safonov, I. G.; Heerding, D. A.; Keenan, R. M.; Price, A.
T.; Erickson-Muller, C. L.; Hopson, C. B.; Levin, J. L.;
Lord, K. A.; Tapley, P. M. Bioorg. Med. Chem. Lett. 2006,
28. Reaction in solution phase between commercial rhodanine
and benzyl bromide afforded a ratio of 4:1 for sulfur/
nitrogen alkylation, see Ref. 8.
1
6, 1212–1216.
5. Zhou, J. F.; Zhu, F. X.; Song, Y. Z.; Zhu, Y. L. Arkivoc
006, 14, 175–180.
29. Kandeel, K. A. Arkivoc 2006, 10, 1–6.
1
1
30. General procedure for the synthesis of 2-amino-5-arylidene-
1,3-thiazol-4(5H)-one 6 under solvent-free microwave irra-
diation: In a cylindrical quartz reactor (Ø = 1.8 cm) was
placed a mixture of compound 4 (10 mmoles) and cyclic
amine 5 (12 mmoles). The reactor was then introduced
2
6. (a) Vicini, P.; Geronikaki, A.; Anastasia, K.; Incerti, M.;
Zani, F. Bioorg. Med. Chem. Lett. 2006, 16, 3859–3864;
(
b) Song, Y.; Connor, D. T.; Doubleday, R.; Sorenson, R.
Ò
J.; Sercel, A.; Unangst, P. C.; Roth, B. D.; Gilbertsen, R.
B.; Chan, K.; Schrier, D. J.; Guglietta, A.; Bornemeier, D.
A.; Dyer, R. D. J. Med. Chem. 1999, 42, 1151–1160.
7. Powers, J. P.; Piper, D. E.; Li, Y.; Mayorga, V.; Anzola,
J.; Chen, J. M.; Jaen, J. C.; Lee, G.; Liu, J.; Peterson, M.
G.; Tonn, G. R.; Ye, Q. Y.; Walker, N. P. C.; Wang, Z. J.
Med. Chem. 2006, 49, 1034–1046.
8. Lohray, B. B.; Bhushan, V.; Rao, P. B.; Madhavan, G. R.;
Murali, N.; Rao, K. N.; Reddy, K. A.; Rajesh, B. M.;
Reddy, P. G.; Chakrabarti, R.; Rajagopalan, R. Bioorg.
Med. Chem. Lett. 1997, 7, 785–788.
into a Synthewave 402 Prolabo microwave reactor. The
stirred mixture was irradiated (after a ramp of 4 min from
20 to 80 °C) at 80 °C (Power level: 30%, 90 W) with
appropriate reaction time (from 20 to 60 min). After
microwave dielectric heating, the crude reaction mixture
was allowed to cool down at room temperature and
ethanol (20 mL) was added in the cylindrical quartz
reactor. The resulting insoluble product 6 was filtered
and dried under high vacuum for 2 h.
1
1
1
31. CAUTION: Owing to elimination of hydrogen sulfide
during the sulfur/nitrogen displacement reaction, the
experiments in the microwave reactor were realized under
ventilated extractor hood.
9. (a) Zhang, M.; Wang, C. D.; Yu, S. L.; Tian, Z. B.; Zhang,
L. Chem. J. Chin. Univ. 1994, 15, 1647–1650; Chem.
Abstr. 1995, 122, 213992z; (b) Alloum, A. B.; Bakkas, S.;
Bougrin, K.; Soufiaoui, M. New. J. Chem. 1998, 22, 809–
32. Selected spectral data for (5Z)-5-(1,3-benzodioxol-5-yl-
methylene)-2-morpholin-4-yl-1,3-thiazol-4(5H)-one
(6a):
8
12.
0. Dijksman, D. J.; Newbold, G. T. R. J. Chem. Soc. 1951,
213–1218.
Yield = 96% from EtOH. Yellow needles, mp = 250–
252 °C. H NMR (300 MHz, (CD ) SO) d: 3.73 (m, 4H,
3 2
1
2
2
2
2
2
1
CH
2
N); 3.90 (m, 2H, CH
2
O); 6.10 (s, 2H, CH
2
O); 7.04 (d,
0
0
1. Yadav, L. D. S.; Tripathi, R. K.; Dwivedi, R.; Singh, H. J.
Agric. Food Chem. 1992, 40, 1700–1702.
2. Commarmot, R.; Didenot, R.; Gardais, J. F. Fr Demande
1H, J = 8.1 Hz, H-6 , Ar); 7.15 (d, 1H, J = 8 Hz, H-5 ,
0
Ar); 7.17 (d, 1H, J = 7.9 Hz, H-6 , Ar); 7.58 (s, 1H, @CH).
1
3
C NMR (75 MHz, (CD
3
)
2
SO) d: 66.06 (CH
2
N); 74.40
0
0
2
5560529, 1985, Chem. Abstr. 1986, 105, 17442.
(CH O); 102.2 (CH O); 109.1 (C-2 , Ar); 109.4 (C-5 , Ar);
113.9 (C@CH, C-4); 125.1 (C-6 , Ar); 126.9 (C-1 , Ar);
2
2
0
0
3. Temperature measured by an IR captor: Prolabo, French
Patent 622 410, 14669 Fr, 1991.
4. Selected spectral data of (5Z)-5-(1,3-benzodioxol-5-ylmeth-
ylene)-2-thioxo-1,3-thiazolidin-4-one (4a): Yield = 65%
0
0
130.6 (@CH); 148.6 (C-4 , Ar); 149.2 (C-3 , Ar); 174.9 (C-
5, C@O). HRMS, m/z: 318.0688 found (calculated for
+
C H N O S, M requires 318.0674).
1
5
14
2
4