Efficient synthesis of 4-ethenylidene-2-oxazolidinones via palladium-catalyzed aminocyclization of 2-butyn-1,4-diol biscarbamates

Tetrahedron Letters

Volumn 38, Issue 22, 1997, Pages 3963-3966

  Kimura, Masanari ^a   Wakamiya, Yoshinori ^a   Horino, Yoshikazu ^a   Tamaru, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 ETHENYLIDENE 2 OXAZOLIDINONE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 0030995589     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00790-9     Document Type: Article

References (10)

1. (a) Tamaru, Y.; Kimura, M.; Tanaka, S.; Kure, S.; Yoshida, Z. Bull. Chem. Soc. Jpn. 1994, 67, 2838.
2. (b) Kimura, M.; Kure, S.; Yoshida, Z.; Tanaka, S.; Fugami, K.; Tamaru, Y. Tetrahedron Lett. 1990, 31, 4887.
3. Ohe, K.; Ishihara, T.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1990, 112, 9646.
4. 3, 100 MHz) δ 21.8, 63.9, 92.6, 103.8, 128.3, 129.9, 134.1, 146.1, 150.3, 192.0. Anal: C, H, N, S.
5. Tsuji, J.; Mandai, T. Angew. Chem. Int. Ed. Engl. 1995, 34, 2589.
6. 3, 400 MHz) δ 1.83 (br s, 3 H), 2.45 (s, 3 H), 2.90 (dm, J = 18.0 Hz, 1 H), 3.05 (dm, J = 18.0 Hz, 1 H), 4.12 (d, J = 9.2 Hz, 1 H), 4.33 (d, J = 9.2 Hz, 1 H), 4.74 (m, 1 H), 5.35 (br d, J = 2.6 Hz, 1 H), 5.55 (br d, J = 2.6 Hz, 1 H), 7.34 (d, J = 8.4 Hz, 2 H), 8.04 (d, J = 8.4 Hz, 2 H). Anal: C, H, N, S.
7. (a) Padwa, A.; Meske, M.; Murphree, S. S.; Watterson, S. H.; Ni, Z. J. Am. Chem. Soc. 1995, 117, 7071.
8. (b) Toda, F.; Tanaka, K.; Sano, I.; Isozaki, T. Angew. Chem. Int. Ed. Engl. 1994, 33, 1757.
9. (c) Narasaka, K.; Hayashi, Y.; Shimazu, H.; Niihara, S. ibid. 1992, 114, 8869.
10. (d) Dolbier, W. R. Jr. Acc. Chem. Res. 1991, 24, 63.