Isochroman-3-ones ones via site-selective ring opening of benzocyclobutenones promoted by lithium tetramethylpiperidide and reaction with aromatic aldehydes

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 8985-8988

  Matsumoto, Takashi ^a   Hamura, Toshiyuki ^a   Kuriyama, Yokusu ^a   Suzuki, Keisuke ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CYCLOBUTANONE DERIVATIVE; LITHIUM DERIVATIVE;

ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS;

EID: 0030782588     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10369-0     Document Type: Article

References (16)

1. Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Matsumoto, T.; Suzuki, K. Synlett 1995, 177-179. Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 3377-3380.
2. Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Matsumoto, T.; Suzuki, K. Synlett 1995, 177-179. Hosoya, T.; Hasegawa, T.; Kuriyama, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 3377-3380.
3. For previous attempts along these lines, see: Bertelli, D. J.; Crews, P. J. Am. Chem. Soc. 1968, 90, 3889-3990. All attempts at effecting the enolization of 1 failed: Slow addition of 1 to an excess of lithium amide brought about the self-aldol product. For a leading book dealing with the chemistry of benzocylobutadiene derivatives, see: Cava, M. P.; Mitchel M. J. Cyclobutadiene and Related Compounds; Academic: New York, 1967.
4. For previous attempts along these lines, see: Bertelli, D. J.; Crews, P. J. Am. Chem. Soc. 1968, 90, 3889-3990. All attempts at effecting the enolization of 1 failed: Slow addition of 1 to an excess of lithium amide brought about the self-aldol product. For a leading book dealing with the chemistry of benzocylobutadiene derivatives, see: Cava, M. P.; Mitchel M. J. Cyclobutadiene and Related Compounds; Academic: New York, 1967.
5. (a) Cava, M. P.; Muth, K. J. Am. Chem. Soc. 1960, 82, 652-654.
6. (b) Amupitan, J. O.; Stansfield, F. J. J. Chem. Soc., Perkin Trans. 1 1974, 1949-1951.
7. (c) Stevens, R. V.; Bisacchi, G. S. J. Org. Chem. 1982, 47, 2393-2396.
8. (d) Gregoire, B.; Carre, M.-C.; Caubere, P. J. Org. Chem. 1986, 51, 1419-1427.
9. For recent reviews on cyclobutene ring opening reactions, see: Durst, T.; Breau, L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 675-697. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 315-399. Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873-2889.
10. For recent reviews on cyclobutene ring opening reactions, see: Durst, T.; Breau, L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 675-697. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 315-399. Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873-2889.
11. For recent reviews on cyclobutene ring opening reactions, see: Durst, T.; Breau, L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 675-697. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 315-399. Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873-2889.
12. 2H spectrum showed the absence of the aldehyde peak, and such a situation persisted even after further addition of the aldehyde in small portions (up to 3 equiv. to Li-TMP), suggesting the adduct is never be of a simple 1:1 stoichiometry. Upon addition of water, the aldehyde signal appeared at the expected position. Prolonged exposure of the aldehyde with Li-TMP, in a separate run, brought about a Cannizzaro-type reaction, giving amide 10 and alcohol 11. (FORMULA PRESENTED)
13. Selected examples on the isochroman-3-one synthesis: (a) Oppolzer, W. Heterocycles 1980, 14, 1615-1630.
14. (b) Shishido, K.; Shitara, E.; Fukumoto, K. J. Am. Chem. Soc. 1985, 107, 5810-5812.
15. (c) Khanapure, S. P.; Biehl, E. R. J. Org. Chem. 1987, 52, 1333-1337.
16. (d) Isobe, K.; Takeda, N.; Mohri, K.; Tsuda, Y. Chem. Pharm. Bull. 1989, 37, 3390-3392.