Addition of silyl enol ethers to imidazoles and thiazoles in the presence of alkyl chloroformate

Chemical Communications

Volumn , Issue 10, 1996, Pages 1217-1218

  Itoh, Takashi ^a   Miyazaki, Michiko ^a   Hasegawa, Hiroshi ^b   Nagata, Kazuhiro ^a   Ohsawa, Akio ^a  

^a SHOWA UNIVERSITY   (Japan)

^b SSP CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000482181     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960001217     Document Type: Article

References (19)

1. T. Itoh, H. Hasegawa, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron Lett., 1992, 33, 5399; T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya and A. Ohsawa, Heterocycles, 1994, 37, 709; T. Itoh, H. Hasegawa, K. Nagata and A. Ohsawa, J. Org. Chem., 1994, 59, 1319; T. Itoh, H. Hasegawa, K. Nagata and A. Ohsawa, Synlett, 1994, 557; T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya, M. Okada and A. Ohsawa, Chem. Pharm. Bull., 1994, 42, 1768; T. Itoh, H. Hasegawa, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron, 1994, 50, 13 089.
2. T. Itoh, H. Hasegawa, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron Lett., 1992, 33, 5399; T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya and A. Ohsawa, Heterocycles, 1994, 37, 709; T. Itoh, H. Hasegawa, K. Nagata and A. Ohsawa, J. Org. Chem., 1994, 59, 1319; T. Itoh, H. Hasegawa, K. Nagata and A. Ohsawa, Synlett, 1994, 557; T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya, M. Okada and A. Ohsawa, Chem. Pharm. Bull., 1994, 42, 1768; T. Itoh, H. Hasegawa, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron, 1994, 50, 13 089.
3. T. Itoh, H. Hasegawa, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron Lett., 1992, 33, 5399; T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya and A. Ohsawa, Heterocycles, 1994, 37, 709; T. Itoh, H. Hasegawa, K. Nagata and A. Ohsawa, J. Org. Chem., 1994, 59, 1319; T. Itoh, H. Hasegawa, K. Nagata and A. Ohsawa, Synlett, 1994, 557; T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya, M. Okada and A. Ohsawa, Chem. Pharm. Bull., 1994, 42, 1768; T. Itoh, H. Hasegawa, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron, 1994, 50, 13 089.
4. T. Itoh, H. Hasegawa, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron Lett., 1992, 33, 5399; T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya and A. Ohsawa, Heterocycles, 1994, 37, 709; T. Itoh, H. Hasegawa, K. Nagata and A. Ohsawa, J. Org. Chem., 1994, 59, 1319; T. Itoh, H. Hasegawa, K. Nagata and A. Ohsawa, Synlett, 1994, 557; T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya, M. Okada and A. Ohsawa, Chem. Pharm. Bull., 1994, 42, 1768; T. Itoh, H. Hasegawa, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron, 1994, 50, 13 089.
5. T. Itoh, H. Hasegawa, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron Lett., 1992, 33, 5399; T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya and A. Ohsawa, Heterocycles, 1994, 37, 709; T. Itoh, H. Hasegawa, K. Nagata and A. Ohsawa, J. Org. Chem., 1994, 59, 1319; T. Itoh, H. Hasegawa, K. Nagata and A. Ohsawa, Synlett, 1994, 557; T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya, M. Okada and A. Ohsawa, Chem. Pharm. Bull., 1994, 42, 1768; T. Itoh, H. Hasegawa, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron, 1994, 50, 13 089.
6. T. Itoh, H. Hasegawa, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron Lett., 1992, 33, 5399; T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya and A. Ohsawa, Heterocycles, 1994, 37, 709; T. Itoh, H. Hasegawa, K. Nagata and A. Ohsawa, J. Org. Chem., 1994, 59, 1319; T. Itoh, H. Hasegawa, K. Nagata and A. Ohsawa, Synlett, 1994, 557; T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya, M. Okada and A. Ohsawa, Chem. Pharm. Bull., 1994, 42, 1768; T. Itoh, H. Hasegawa, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron, 1994, 50, 13 089.
7. The chemistry of N-alkoxycarbonylpyridinium salts has been studied by several groups. See: R. Yamaguchi, T. Hamasaki, T. Sasaki, T. Ohta, K. Utimoto, S. Kozima and H. Takaya, J. Org. Chem., 1993, 58, 1136; D. L. Comins and S. O'Connor, Advances in Heterocyclic Chemistry, vol. 44. ed. A. R. Katritizky, Academic Press, San Diego, 1988, pp. 199-267, and references cited therein.
8. The chemistry of N-alkoxycarbonylpyridinium salts has been studied by several groups. See: R. Yamaguchi, T. Hamasaki, T. Sasaki, T. Ohta, K. Utimoto, S. Kozima and H. Takaya, J. Org. Chem., 1993, 58, 1136; D. L. Comins and S. O'Connor, Advances in Heterocyclic Chemistry, vol. 44. ed. A. R. Katritizky, Academic Press, San Diego, 1988, pp. 199-267, and references cited therein.
9. Recently, in situ formation of allyltin was shown to be useful for our reaction system. J.-Y. Zhou, Z.-G. Chen and S.-H. Wu, Synlett, 1995, 1117.
10. It was reported that benzyltributyltin reacts selectively with N-alkoxycarbonyl pyridinium salts at the C-4 positions; see: R. Yamaguchi, M. Moriyasu and M. Kawanishi, Tetrahedron Lett., 1986, 27, 211. Ethyl(tributylstannyl)acetate was shown to be a versatile reagent for the carboethoxymethylation of functionalized pyridines; see T. G. Murali Dhar and C. Gluchowski, Tetrahedron Lett., 1994, 35, 989. These reagents showed poor reactivity towards other heterocycles such as imidazole, thiazole and pyridazine.
11. It was reported that benzyltributyltin reacts selectively with N-alkoxycarbonyl pyridinium salts at the C-4 positions; see: R. Yamaguchi, M. Moriyasu and M. Kawanishi, Tetrahedron Lett., 1986, 27, 211. Ethyl(tributylstannyl)acetate was shown to be a versatile reagent for the carboethoxymethylation of functionalized pyridines; see T. G. Murali Dhar and C. Gluchowski, Tetrahedron Lett., 1994, 35, 989. These reagents showed poor reactivity towards other heterocycles such as imidazole, thiazole and pyridazine.
12. The 1,3-di(acyl)midazolium salt reacted with 1-acylimidazole to give a bisimidazole derivative in good yield. See: E. Regel, Liebigs Ann. Chem., 1977, 159.
13. J. A. M. Bastiaansen, Synthesis. 1978, 633; B. C. Uff, D. L. W. Burford and Y.-P. Ho, J. Chem. Res. (S), 1989, 386. Y. H. R. Jois and H. W. Gibson, J. Org. Chem., 1991, 56, 865; Y. H. R. Jois, M. A. G. Berg, J. S. Merola and H. W. Gibson, Tetrahedron Lett., 1991, 32, 2997.
14. J. A. M. Bastiaansen, Synthesis. 1978, 633; B. C. Uff, D. L. W. Burford and Y.-P. Ho, J. Chem. Res. (S), 1989, 386. Y. H. R. Jois and H. W. Gibson, J. Org. Chem., 1991, 56, 865; Y. H. R. Jois, M. A. G. Berg, J. S. Merola and H. W. Gibson, Tetrahedron Lett., 1991, 32, 2997.
15. J. A. M. Bastiaansen, Synthesis. 1978, 633; B. C. Uff, D. L. W. Burford and Y.-P. Ho, J. Chem. Res. (S), 1989, 386. Y. H. R. Jois and H. W. Gibson, J. Org. Chem., 1991, 56, 865; Y. H. R. Jois, M. A. G. Berg, J. S. Merola and H. W. Gibson, Tetrahedron Lett., 1991, 32, 2997.
16. J. A. M. Bastiaansen, Synthesis. 1978, 633; B. C. Uff, D. L. W. Burford and Y.-P. Ho, J. Chem. Res. (S), 1989, 386. Y. H. R. Jois and H. W. Gibson, J. Org. Chem., 1991, 56, 865; Y. H. R. Jois, M. A. G. Berg, J. S. Merola and H. W. Gibson, Tetrahedron Lett., 1991, 32, 2997.
17. To the best of our knowledge, there is only one report concerning reactivity of N-alkoxycarhonyl quaternary salts of azoles. Dondoni et al. reported the reaction of N-ethoxycarbonylthiazolium salts with organometallic reagents such as alkyllithium, Grignard reagents and ketene silyl acetals, but the reaction was performed as a stepwise procedure. See: A. Dondoni, T. Dall'Occo, G. Fantin, M. Fogagnolo and A. Medici, Tetrahedron Lett.. 1984, 25, 3633; For the applications of the addition of metallo enolates to the six-membered azaaromatics, see: D. L. Comins and H. Hong, J. Org. Chem., 1993, 58, 5035, and references cited therein.
18. To the best of our knowledge, there is only one report concerning reactivity of N-alkoxycarhonyl quaternary salts of azoles. Dondoni et al. reported the reaction of N-ethoxycarbonylthiazolium salts with organometallic reagents such as alkyllithium, Grignard reagents and ketene silyl acetals, but the reaction was performed as a stepwise procedure. See: A. Dondoni, T. Dall'Occo, G. Fantin, M. Fogagnolo and A. Medici, Tetrahedron Lett.. 1984, 25, 3633; For the applications of the addition of metallo enolates to the six-membered azaaromatics, see: D. L. Comins and H. Hong, J. Org. Chem., 1993, 58, 5035, and references cited therein.
19. K. Akiba, Y. Nishihara and M. Wada, Tetrahedron Lett., 1983, 24, 5269.