A new and general route to N-unsubstituted azomethine ylides from N-(silylmethyl)thioureas: Cycloaddition of synthetic equivalents of nonstabilized aminonitrile ylides

Chemistry Letters

Volumn , Issue 9, 1997, Pages 945-946

  Tsuge, Otohiko ^a   Hatta, Taizo ^a   Kakura, Yoshikazu ^a   Tashiro, Hideki ^a   Maeda, Hironori ^a   Kakehi, Akikazu ^b  

^a SOJO UNIVERSITY   (Japan)

^b SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031327643     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.945     Document Type: Article

References (14)

1. O. Tsuge and S. Kanemasa, "Advances in Heterocyclic Chemistry," ed by A. R. Katritzky, Academic Press (1989), Vol. 45, pp 231.
2. The desilylative route to azomethine ylides has been reviewed: a) E. Vedejs and F. G. West, Chem. Rev., 86, 941 (1986).
3. b) Y. Terao, M. Aono, and K. Achiwa, Heterocyles, 27, 981 (1988).
4. O. Tsuge, S. Kanemasa, A. Hatada, and K. Matsuda, Chem. Lett., 1984, 801; Bull. Chem. Soc. Jpn., 59, 2537 (1986).
5. O. Tsuge, S. Kanemasa, A. Hatada, and K. Matsuda, Chem. Lett., 1984, 801; Bull. Chem. Soc. Jpn., 59, 2537 (1986).
6. O. Tsuge, S. Kanemasa, T. Yamada, and K. Matsuda, J. Org. Chem., 52, 2523 (1987).
7. O. Tsuge, S. Kanemasa, and K. Matsuda, J. Org. Chem., 51, 1997 (1986).
8. O. Tsuge, S. Kanemasa, and K. Matsuda, Chem. Lett., 1985, 1411.
9. It has been reported that the reaction of 1-methyl-2-[(methyl-thio(trimethylsilylimino)methylimino]-1,2-dihydropyridine with carbonyl compounds in the presence of fluoride ion afforded the formal [3+2] cycloadducts of the aminonitrile ylide (S. Kohra, K. Ueda, and Y. Tominaga, Chem. Pharm. Bull., 43, 204 (1995).
10. O. Tsuge, S. Kanemasa, and K. Matsuda, J. Org. Chem., 49, 2688 (1984).
11. The structures of all the new compounds in this paper were fully characterized by the spectroscopic and elementary analysis.
12. No 1:2 adducts (7b-7d) were obtained from the reaction of the corresponding 1:1 adducl (5) with 4 in the presence or absence of CsF in refluxing DME. The reaction pathway for the formation of 7 is not clear.
13. 3, R=0.045, Rw=0.051.
14. Position of double bond in each cycloadduct has been found to depend upon the electronic nature and the steric size of the substituents (lit. 5). The double bond in pyrrolines presumably migrate to the thermodynamically most stable location.