Inter- and intramolecular Diels-Alder reactions using a highly reactive 1-aza-1,3-butadiene, ethyl (E)-3-(1,3-benzothiazol-2-yl)-3-cyanopropenoate

Tetrahedron

Volumn 52, Issue 3, 1996, Pages 733-742

  Sakamoto, Masanori ^a   Nagano, Mayumi ^a   Suzuki, Yoko ^a   Satoh, Kumiko ^a   Tamura, Osamu ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

BETULACEAE; STAPHYLOCOCCUS PHAGE 3A;

EID: 0030047761     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01033-5     Document Type: Article

References (21)

1. For reviews, Boger D. L. and Weinreb S. M., Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, San Diego, 1987; Boger D. L., in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon Press, Oxford, 1991, vol. 5, pp. 451-512.
2. For reviews, Boger D. L. and Weinreb S. M., Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, San Diego, 1987; Boger D. L., in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon Press, Oxford, 1991, vol. 5, pp. 451-512.
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13. (a) Sakamoto, M.; Nozaka, A.; Shimamoto, M.; Ozaki, H.; Suzuki, Y.; Yoshioka, S.; Nagano, M.; Okamura, K.; Date, T.; Tamura, O. Chem. Pharm. Bull., 1994, 42, 1367-1369.
14. (b) Idem, J. Chem. Soc., Perkin Trans. 1, 1995, 1759-1770.
15. Part of this work has been the subject of a preliminary communication. Sakamoto, M.; Nagano, M.; Suzuki, Y.; Tamura, O., Chem. Pharm. Bull., in press.
16. In contrast to the reaction of 2 with 3d (entry 4), reaction of 1a (Y = H) with 3d takes 24 h at 120°C under neat condition. Reactivity of diene (2) introduced ester group at diene 4-position is apparently much higher than that of 1a. Brief AM1 calculation of s-cis conformation of 1a (Y = H) and 2 supports this difference of reactivities. Thus, the calculation shows that the diene (2) has lower LUMO (-1.6 eV) than 1a (Y = H) (-1.2 eV). In addition, the magnitude of C4 coefficient of 2 (0.47) is larger than that of 1a (0.44). These values in the calculation of 2 are favorable for regio-selective diene-LUMO controlled (inverse type) Diels-Alder reaction with high regioselectivity. Accordingly, diene (2) smoothly reacts with electron-rich dienophiles (3a-e) (HOMO: between -9.5 and -8.5 eV). For discussions on reactivity of 1-aza-1,3-butadiene using computation, see ref. 4b and 6b. For AM1, see, Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
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19. (c) Tamura, O.; Okabe, T.; Yamaguchi, T.; Gotanda, K.; Noe, K.; Sakamoto, M. Tetrahedron, 1995, 51, 107-118.
20. (d) Tamura, O.; Okabe, T.; Yamaguchi, T.; Kotani, J.; Gotanda, K.; Sakamoto, M. Tetrahedron, 1995, 51, 119-128.
21. Otera, J.; Dan-oh, N.; Nozaki, H. J. Org. Chem., 1991, 56, 5307-5311.