Regiocontrolled benzannulation of diaryl(gem-dichlorocyclopropyl)methanols for the synthesis of 'unsymmetrically' substituted α-arylnaphthalenes

Tetrahedron Letters

Volumn 38, Issue 41, 1997, Pages 7195-7198

  Nishii, Yoshinori ^a   Yoshida, Taichi ^a   Tanabe, Yoo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHALENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030666815     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01713-9     Document Type: Article

References (20)

1. For recent representative studies: (a) Katritzky, A. R.; Zhang, G.; Xie, L. J. Org. Chem. 1997, 62, 721.
2. (b) Kobayashi, K.; Uneda, T.; Takada, K.; Tanaka, H.; Kitamura, T.; Morikawa, O.; Konishi, H. J. Org. Chem. 1997, 62, 664.
3. (c) Cotelle, P.; Catteau, J-P. Tetrahedron Lett. 1997, 38, 2969.
4. (d) Charlton, J. L.; Oleschuk, C. J.; Chee, G-L. J. Org. Chem. 1996, 61, 3452.
5. (a) Tanabe, Y.; Seko, S.; Nishii, Y.; Yoshida, T.; Utsumi, N.; Suzukamo, G. J. Chem. Soc., Perkin Trans. 1, 1996, 2157.
6. (b) Nishii, Y.; Tanabe, Y. J. Chem. Soc., Perkin Trans. 1, 1997, 477.
7. For reviews: (a) Ward, R. S. Chem. Soc. Rev., 1982, 11, 75.
8. (b) Ward, R. S. Natural Product Report, 1995, 12, 183.
9. (c) Ohmizu, H.; Iwasaki, T. J. Synth. Org. Chem. Jpn., 1995, 53, 593.
10. 1H NMR δ 7.20-7.24 (2H, m), 7.26-7.34 (3H, m). (Formula presented)
11. 3) δ 2.18 (3H, s), 2.62 (3H, s), 7.29-7.32 (2H, m), 7.51-7.52 (1H, m), 8.34 (1H, d, J = 8.5 Hz).
12. 3) δ 2.18 (3H, s), 2.62 (3H, s), 7.21-7.22 (1H, m), 7.42-7.46 (1H, m), 7.47-7.51 (2H, m).
13. 3) δ 1.85 (3H, s), 1.89 (3H, s), 7.10-7.30 (2H, m), 7.40-7.60 (3H, m).
14. 3) δ 2.05 (3H, s), 6.65 (1H, s), 7.10-7.20 (2H, m), 7.23-7.60 (3H, m).
15. 3) δ 1.16 (3H, s), 1.27 (1H, d, J = 7.3 Hz), 2.41 (3H, s), 2.52 (1H, d, J = 7.3 Hz), 2.60-2.85 (1H, br, OH), 7.25 (2H, d, J = 8.0 Hz), 7.42 (2H, d, J = 8.0 Hz). 1d′: colorless crystals; mp 44-49 °C; δ 1.19(3H, s), 1.28 (1H, d, J = 7.3 Hz), 2.34 (3H, s), 2.52 (1H, d, J = 7.3 Hz), 2.72-2.84 (1H, br, OH), 7.05 (2H, d, J = 8.4 Hz), 7.09 (2H, d, J = 8.4 Hz). 1e: colorless crystals; mp 71-75 °C; δ 1.16 (3H, s), 1.30 (1H, d, J = 7.3 Hz), 2.51 (1H, d, J = 7.3 Hz), 2.70-3.00 (1H, br, OH), 7.41 (2H, d, J = 8.5 Hz), 7.47 (2H, d, J = 8.5 Hz). 1e′: colorless crystals; mp 98-102 °C; δ 1.19 (3H, s), 1.28 (1H, d, J = 7.3 Hz), 2.49 (1H, d, J = 7.3 Hz), 2.78-2.86 (1H, br, OH), 7.11 (2H, d, J = 9.0 Hz), 7.24 (2H, d, J = 9.0 Hz).
16. 3) δ 2.21 (3H, s), 2.46 (3H, s), 7.13 (2H, d, J = 7.5 Hz), 7.31 (2H, d, J = 7.5 Hz), 7.54 (1H, s). 2d/B: a colorless oil; δ 2.16 (3H, s), 2.36 (3H, s), 7.15 (1H, s), 7.34 (1H, d, J = 8.9 Hz), 7.45 (1H, s), 8.15 (1H, d, J = 8.9 Hz). On the reaction using 1d and 1d′, following by-products were detected: i) 1,1-dichloro-2,2-dihydro-3-methyl-4-(p-tolyl)-5,6,7,8-tetradeuterionaphthalene (48%), δ 2.04 (3H, s), 2.31 (3H, s), 3.69 (2H, s), 7.08-7.15 (4H, m); iii) 1,1-dichloro-2,2-dihydro-3,7-dimethyl-4-(pentadeuteriophenyl)naphthalene (20%), δ 2.02 (3H, s), 2.32 (3H, s), 3.73 (2H, s), 7.00-7.12 (3H, m); and iv) 4,4-dichloro-2-methyl-1-(pentadeuteriophenyl)-1-(p-tolyl)-1,3-butadiene (42%), δ 2.08 (3H, s), 2.36 (3H, s), 6.55 (1H, s), 7.03-7.14 (4H, m). 2e/A: a colorless oil; δ 2.20 (3H, s), 7.18 (2H, d, J = 8.5 Hz), 7.48 (2H, d, J = 8.5 Hz), 7.53 (1H, s). 2e/B: a colorless oil; δ 2.19 (3H, s), 7.37 (1H, d, J = 2.0 Hz), 7.45 (1H, dd, J = 2.0 Hz, J = 9.5 Hz), 7.52 (1H, s), 8.20 (1H, d, J = 9.5 Hz). On the reaction using 1e and 1e′, following by-products were detected: ii) See Ref. 11; and iv) 4,4-dichloro-1-(4-chlorophenyl)-2-methyl-1-(pentadeuteriophenyl)-1,3-butadiene (42%), δ 2.01 (3H, s), 6.48 (1H, s), 7.03 (2H, d, J = 8.3 Hz), 7.24 (2H, d, J = 8.3 Hz).
17. 3) δ 2.05 (3H, s), 6.48 (1H, s), 7.04 (2H, d, J = 8.6 Hz), 7.24 (2H, d, J = 8.6 Hz). We suppose that the formation of this product is due to the inherent low reactivity of 4-chlorophenyl.
18. Even 3,4-dimethoxyphenyl group is considerably more reactive than 3,4-methylenedioxyphenyl group: Sha, C-K.; Young, J-J.; Yeh, C-P.; Chang, S-C.; Wang, S-L. J. Org. Chem. 1991, 56, 2694.
19. -1.
20. 2 Tetrahedron Letters, Vol. 38, No. 41, pp. 7199-7202, 1997