Reaction of 3-aralkylsulfonyl-2-(N-cyanoimino)-thiazolidines with oxygen nucleophiles

Heterocycles

Volumn 42, Issue 1, 1996, Pages 265-272

  Tanaka, Tetsuaki ^a   Nakamoto, Yumi ^a   Maekawa, Kaori ^a   Watanabe, Mayumi ^a   Nishihara, Chihiro ^a   Iwata, Chuzo ^a   Uchida, Shuji ^b  

^a OSAKA UNIVERSITY   (Japan)

^b SETSUNAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343058716     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s16     Document Type: Article

References (11)

1. R. Neidlein and H. Reuter, Arch. Pharm., 1972, 305, 731.
2. C. Iwata, M. Watanabe, S. Okamoto, M. Fujimoto, M. Sakae, M. Katsurada, and T. Imanishi, Heterocycles, 1988, 27, 323.
3. C. Iwata, M. Fujimoto, M. Watanabe, T. Kawakami, N. Maeda, T. Imanishi, and T. Tanaka, Heterocycles, 1991, 32, 2471.
4. C. Iwata, M. Fujimoto, M. Watanabe, T. Kawakami, Y. Nakamoto, M. Sakae, M. Katsurada, T. Imanishi, and T. Tanaka, J. Chem. Soc., Chem. Commun., 1992, 1379.
5. C. Iwata, M. Fujimoto, S. Okamoto, C. Nishihara, M. Sakae, M. Katsurada, M. Watanabe, T. Kawakami, T. Tanaka, and T. Imanishi, Heterocycles, 1990, 31, 1601. Recently, a similar triazole formation was observed by Pätzel et al: M. Pätzel, A. Schulz, J. Liebscher, W. Richter, and M. Richter, J. Heterocycl. Chem., 1992, 29, 1209.
6. C. Iwata, M. Fujimoto, S. Okamoto, C. Nishihara, M. Sakae, M. Katsurada, M. Watanabe, T. Kawakami, T. Tanaka, and T. Imanishi, Heterocycles, 1990, 31, 1601. Recently, a similar triazole formation was observed by Pätzel et al: M. Pätzel, A. Schulz, J. Liebscher, W. Richter, and M. Richter, J. Heterocycl. Chem., 1992, 29, 1209.
7. T. Tanaka, M. Watanabe, Y. Nakamoto, K. Okuno, K. Maekawa, and C. Iwata, J. Chem. Soc., Chem. Commun., 1994, 2301.
8. C. Iwata, M. Watanabe, S. Okamoto, M. Fujimoto, M. Sakae, M. Katsurada, and T. Imanishi, Synthesis, 1988, 261.
9. Although the formation of alkyl sulfonates was not confirmed experimentally, we proved independently that NCT anion prepared from NCT (1a) and NaH in DMF was alkylated by ethyl methanesulfonate to give 3-ethyl-NCT (1c: R=Et) in good yield.
10. D. N. Jones, "Comprehensive Organic Chemistry," Vol. 3, ed. by D. H. R. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979, p. 347.
11. A. P. Kozikowsky and Y.-Y. Chen, J. Org. Chem., 1981, 46, 5248.