Generation and diels-alder reactions of t-butyl 2H-azirine-3-carboxylate

Tetrahedron Letters

Volumn 39, Issue 41, 1998, Pages 7579-7582

  Alves, Maria José ^a   Gilchrist, Thomas L ^b  

^a UNIVERSITY OF MINHO   (Portugal)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; TERT BUTYL 2H AZIRINE CARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

EID: 0032497610     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01617-7     Document Type: Article

References (21)

1. 1 Alves, M.J.; Gilchrist, T.L. J. Chem. Soc., Perkin Trans. 1, 1998, 299-303.
2. 2 Anderson, D.J.; Hassner, A. Synthesis, 1975, 483-495.
3. 3 Smolinsky, G.; Pryde, C.A. J. Org. Chem., 1968, 33, 2411-2416; Bestmann, H.J.; Kunstmann, R. Chem. Ber., 1969, 102, 1816-1832: Shin, C.; Yonezawa, Y.; Suzuki, K.; Yoshimura, J. Bull. Chem. Soc. Jpn., 1978, 51, 2614-2617; L'abbe, G.; Dekerk, J.P.; Van Stappen, P. Bull. Soc. Chim. Belg., 1981, 90, 1073-1074; Knittel, D. Synthesis, 1985, 186-188; Hickey, D.M.B.; Moody, C.J.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1986, 1119-1122; Watanabe, T.; Takahashi, H.; Kamakura, H.; Sakaguchi, S.; Osaki, M.; Toyama, S.; Mizuma, Y.; Ueda, I.; Murakami, Y. Chem. Pharm. Bull. 1991, 39, 3145-3152.
4. 3 Smolinsky, G.; Pryde, C.A. J. Org. Chem., 1968, 33, 2411-2416; Bestmann, H.J.; Kunstmann, R. Chem. Ber., 1969, 102, 1816-1832: Shin, C.; Yonezawa, Y.; Suzuki, K.; Yoshimura, J. Bull. Chem. Soc. Jpn., 1978, 51, 2614-2617; L'abbe, G.; Dekerk, J.P.; Van Stappen, P. Bull. Soc. Chim. Belg., 1981, 90, 1073-1074; Knittel, D. Synthesis, 1985, 186-188; Hickey, D.M.B.; Moody, C.J.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1986, 1119-1122; Watanabe, T.; Takahashi, H.; Kamakura, H.; Sakaguchi, S.; Osaki, M.; Toyama, S.; Mizuma, Y.; Ueda, I.; Murakami, Y. Chem. Pharm. Bull. 1991, 39, 3145-3152.
5. 3 Smolinsky, G.; Pryde, C.A. J. Org. Chem., 1968, 33, 2411-2416; Bestmann, H.J.; Kunstmann, R. Chem. Ber., 1969, 102, 1816-1832: Shin, C.; Yonezawa, Y.; Suzuki, K.; Yoshimura, J. Bull. Chem. Soc. Jpn., 1978, 51, 2614-2617; L'abbe, G.; Dekerk, J.P.; Van Stappen, P. Bull. Soc. Chim. Belg., 1981, 90, 1073-1074; Knittel, D. Synthesis, 1985, 186-188; Hickey, D.M.B.; Moody, C.J.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1986, 1119-1122; Watanabe, T.; Takahashi, H.; Kamakura, H.; Sakaguchi, S.; Osaki, M.; Toyama, S.; Mizuma, Y.; Ueda, I.; Murakami, Y. Chem. Pharm. Bull. 1991, 39, 3145-3152.
6. 3 Smolinsky, G.; Pryde, C.A. J. Org. Chem., 1968, 33, 2411-2416; Bestmann, H.J.; Kunstmann, R. Chem. Ber., 1969, 102, 1816-1832: Shin, C.; Yonezawa, Y.; Suzuki, K.; Yoshimura, J. Bull. Chem. Soc. Jpn., 1978, 51, 2614-2617; L'abbe, G.; Dekerk, J.P.; Van Stappen, P. Bull. Soc. Chim. Belg., 1981, 90, 1073-1074; Knittel, D. Synthesis, 1985, 186-188; Hickey, D.M.B.; Moody, C.J.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1986, 1119-1122; Watanabe, T.; Takahashi, H.; Kamakura, H.; Sakaguchi, S.; Osaki, M.; Toyama, S.; Mizuma, Y.; Ueda, I.; Murakami, Y. Chem. Pharm. Bull. 1991, 39, 3145-3152.
7. 3 Smolinsky, G.; Pryde, C.A. J. Org. Chem., 1968, 33, 2411-2416; Bestmann, H.J.; Kunstmann, R. Chem. Ber., 1969, 102, 1816-1832: Shin, C.; Yonezawa, Y.; Suzuki, K.; Yoshimura, J. Bull. Chem. Soc. Jpn., 1978, 51, 2614-2617; L'abbe, G.; Dekerk, J.P.; Van Stappen, P. Bull. Soc. Chim. Belg., 1981, 90, 1073-1074; Knittel, D. Synthesis, 1985, 186-188; Hickey, D.M.B.; Moody, C.J.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1986, 1119-1122; Watanabe, T.; Takahashi, H.; Kamakura, H.; Sakaguchi, S.; Osaki, M.; Toyama, S.; Mizuma, Y.; Ueda, I.; Murakami, Y. Chem. Pharm. Bull. 1991, 39, 3145-3152.
8. 3 Smolinsky, G.; Pryde, C.A. J. Org. Chem., 1968, 33, 2411-2416; Bestmann, H.J.; Kunstmann, R. Chem. Ber., 1969, 102, 1816-1832: Shin, C.; Yonezawa, Y.; Suzuki, K.; Yoshimura, J. Bull. Chem. Soc. Jpn., 1978, 51, 2614-2617; L'abbe, G.; Dekerk, J.P.; Van Stappen, P. Bull. Soc. Chim. Belg., 1981, 90, 1073-1074; Knittel, D. Synthesis, 1985, 186-188; Hickey, D.M.B.; Moody, C.J.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1986, 1119-1122; Watanabe, T.; Takahashi, H.; Kamakura, H.; Sakaguchi, S.; Osaki, M.; Toyama, S.; Mizuma, Y.; Ueda, I.; Murakami, Y. Chem. Pharm. Bull. 1991, 39, 3145-3152.
9. 3 Smolinsky, G.; Pryde, C.A. J. Org. Chem., 1968, 33, 2411-2416; Bestmann, H.J.; Kunstmann, R. Chem. Ber., 1969, 102, 1816-1832: Shin, C.; Yonezawa, Y.; Suzuki, K.; Yoshimura, J. Bull. Chem. Soc. Jpn., 1978, 51, 2614-2617; L'abbe, G.; Dekerk, J.P.; Van Stappen, P. Bull. Soc. Chim. Belg., 1981, 90, 1073-1074; Knittel, D. Synthesis, 1985, 186-188; Hickey, D.M.B.; Moody, C.J.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1, 1986, 1119-1122; Watanabe, T.; Takahashi, H.; Kamakura, H.; Sakaguchi, S.; Osaki, M.; Toyama, S.; Mizuma, Y.; Ueda, I.; Murakami, Y. Chem. Pharm. Bull. 1991, 39, 3145-3152.
10. 4 Hassner, A.; Fowler, F.W. J. Org. Chem., 1968, 33, 2686-2691.
11. 5 Kakimoto, M-.a.; Kai, M.; Kondo, K. Chem. Lett., 1982, 525-526; Ghosh, S.K.; Verma, R.; Ghosh, U.; Mamdapur, V.R. Bull. Chem. Soc. Jpn., 1996, 69, 1705-1711.
12. 5 Kakimoto, M-.a.; Kai, M.; Kondo, K. Chem. Lett., 1982, 525-526; Ghosh, S.K.; Verma, R.; Ghosh, U.; Mamdapur, V.R. Bull. Chem. Soc. Jpn., 1996, 69, 1705-1711.
13. 3) 1.53 (9 H, s), 5.26 (1 H, s) and 5.71 (1 H, s).
14. 7 A dilute (44 millimolar) solution in heptane was used. In more concentrated solutions there are significant amounts of a by-product, which has been identified as di-t-butyl pyrrole-2,5-dicarboxylate. This is probably formed by dimerisation of the azide through 1,3-dipolar cycloaddition, followed by loss of nitrogen from a 1,2,3-triazole: (equation presented)
15. 8 The azirine was identified by NMR: δ 1.56 (9 H, s) and 1.93 (2 H, s).
16. 3) 0.21 (9 H, s), 1.48 (9 H, S), 1.98 (2 H, s, 2 H-7), 2.47 (1 H, d, J 18.0, H-5), 2.66 (1 H, d, J 18.0, H-5), 3.51 (3 H, s), 4.48 (1 H, br s, H-3) and 4.91 (1 H, s, H-2).
17. 10 Bernet, B.; Murty, A.R.C.B.; Vasella, A. Helv. Chim. Acta, 1990, 73, 940-958; Paulsen, H.; Matzke, M.; Orthen, B.; Nuck, R.; Reutter, W. Liebigs Ann. Chem., 1990, 953-963.
18. 10 Bernet, B.; Murty, A.R.C.B.; Vasella, A. Helv. Chim. Acta, 1990, 73, 940-958; Paulsen, H.; Matzke, M.; Orthen, B.; Nuck, R.; Reutter, W. Liebigs Ann. Chem., 1990, 953-963.
19. 1) and 189.99 (C-5).
20. 12 Gupta, R.C.; Larsen, D.S.; Stoodley, R.J.; Slawin, A.M.Z.; Williams, D.J. J. Chem. Soc., Perkin Trans. I, 1989, 739-749.
21. 3) 0.19 (9 H, s), 1.49 (9 H, s), 1.52 (3 H, s), 1.88 (1 H, s, H-7), 1.92 (1 H, s, H-7), 2.00, 2.03, 2.05 and 2.08 (each 3 H, s), 2.52 (1 H, d, J 17.9, H-5), 2.76 (1 H, d, J 17.9, H-5), 3.75 (1 H, ddd, J 9.4, 4.9 and 2.4, H-5′), 4.13 (1 H, dd, J 12.1 and 2.4, H-6′), 4.25 (1 H, dd, J 12.1 and 4.9, H-6′), 5.01 (1 H, dd, J 9.6 and 8.1, H-2′), 5.11 (1 H, approx. t, 79.8, H-3′), 5.24 (1 H, t, J 9.4, H-4′), 5.26 (1 H, d, J 8.1, H-1′) and 5.27 (1 H, s, H-2).