S. Cheng, D. D. Comer / Tetrahedron Letters 43 (2002) 1179–1181
1181
Table 2. Thiols used for Michael addition step
K.-S.; Pan, J.-F.; Chen, K. Tetrahedron Lett. 2000, 41,
6815; (f) Castelli, V.v. A.; Cort, A. D.; Mandolini, L.;
Reinhoudt, D. N.; Schiaffino, L. Chem. Euro. J. 2000, 6,
1193; (g) Kobayashi, S.; Ogawa, C.; Kawamura, M.;
Sugiura, M. Synlett 2001, 983.
7. (a) Sternberg, J. A.; Geffken, D.; Adams, J. B., Jr.;
Postages, R.; Sternberg, C. G.; Campbell, C. L.; Moberg,
W. K. Pest. Manag. Sci. 2001, 57, 143; (b) Sternberg, J.
A.; Geffken, D.; Adams, J. B., Jr.; Postages, R.; Stern-
berg, C. G.; Campbell, C. L.; Moberg, W. K. ACS Symp.
Ser. 1998, 686, 216.
8. (a) Feuer, H.; Rubinstein, H. J. Am. Chem. Soc. 1958, 80,
5873; (b) Feuer, H.; Asunskis, J. P. J. Org. Chem. 1962,
27, 4684.
9. (a) Igarashi, Y.; Watanabe, S. J. Chem. Soc. Jpn. 1990,
11, 1284; (b) Shih, H.; Rankin, G. O. J. Heterocyclic
Chem. 1977, 14, 349; (c) Briere, J.; Charpentier, P.;
Dupas, G.; Queguiner, G.; Bourguignon, J. Tetrahedron
1997, 53, 2075.
10. Pelletier, S. W.; Venkov, A. P.; Finer-Moore, J.; Mody,
N. V. Tetrahedron Lett. 1980, 21, 809.
11. Example procedure: N-anilinomaleimide(2a): Maleic any-
hydride (5.0 g, 51.0 mmol) was dissolved in anhydrous
THF (100 mL) and phenylhydrazine (5.5 g, 5.0 mL, 51.0
mmol) was added in an N2 atmosphere. The yellow
solution was stirred for 2 h at room temperature. Thionyl
chloride (7.3 g, 4.5 mL, 61.2 mmol) was then added to
the mixture over 2 min. The reaction was then heated to
65°C over 30 min and stirred for an additional 30 min at
65°C. The resulting brown mixture was allowed to cool
and concentrated in vacuo to give a dark-brown oily
solid. Minimal dry EtOH was added to create a thick
suspension. The solid was vacuum filtered and washed
twice with dry EtOH. The resulting orange crystalline
solid was dried overnight in vacuo to yield N-anilino-
maleimide(2a) (6.0 g, 63%, >95% pure by LC/MS), mp
145–148, 13C NMR (DMSO-d6, 300 MHz) l 113.284,
1
119.698, 121.046, 129.115, 140.838, 143.698, 167.014; H
NMR (DMSO-d6, 300 MHz) l 6.55 (d, 1H, J=3.0 Hz),
6.89–6.86 (m, 1H), 7.28–7.24 (m, 4H), 7.79 (d, 1H, J=3.0
Hz); C10H8N2O2=188.19; MS: [M+H]+=189.
References
12. Example procedure: 3-phenylsulfanyl-1-phenylamino-
pyrrolidine-2,5-dione (1,R1,R2=Ph): N-Anilinomaleim-
ide(I) (0.037 g, 0.2 mmol) was dissolved in distilled
DMF (1 mL) and benzenethiol (0.066 g, 0.6 mmol) was
added. Neutral alumina (0.110 g) was added and the
mixture was stirred at 80°C for 1 h. Mixture was allowed
to cool and was filtered through a 0.2 micron filter to
remove the alumina. The resulting solution was then
directly injected onto a reverse phase HPLC purification
system and purified. Pure fractions were collected and
concentrated in vacuo to yield 3-phenylsulfanyl-1-phenyl-
amino-pyrrolidine-2,5-dione (1,R1,R2=Ph) as a white solid
1. Posner, G. H. Angew. Chem., Int. Ed. Engl. 1978, 17, 487.
2. Posner, G. H.; Rogers, D. G. J. Am. Chem. Soc. 1977,
99, 8208.
3. Posner, G. H.; Gurria, G. M.; Bublak, K. A. J. Org.
Chem. 1977, 42, 3173.
4. Ranu, B. C.; Bhar, S. Tetrahedron 1992, 48, 1327.
5. Macphail, A. T.; Oran, K. D.; Furokawa, H.; Piantadosi,
C. Tetrahedron Lett. 1973, 14, 4641.
6. (a) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am.
Chem. Soc. 1998, 120, 4043; (b) Saito, M.; Nakajima, M.;
Hashimoto, S. Tetrahedron 2000, 56, 9589; (c) Kou-
locheri, S. D.; Magiatis, P.; Skaltounis, A.-L.; Haroutou-
nian, S. A. Tetrahedron 2000, 56, 6135; (d) Kamimura,
A.; Kawahara, F.; Omata, Y.; Murakami, N.; Morita,
R.; Otake, H.; Mitsudera, H.; Shirai, M.; Kakehi, A.
Tetrahedron Lett. 2001, 42, 8497; (e) Lin, C.-H.; Yang,
1
(0.039 g, 66%, 99% pure by LC/MS), H NMR (CDCl3,
300 MHz) l 2.78 (dd, 1H, J=4.3 Hz and J=4.1 Hz),
3.23 (dd, 1H, J=9.2 Hz and J=9.1 Hz), 4.05 (dd, 1H,
J=9.1 Hz and J=4.2 Hz), 6.53–7.53 (m, 10H);
C16H14N2O2S=298.37; MS: [M+H]+=299.