Annulated ring-systems by Domino-Heck-aldol-condensation and Domino-Heck-Michael-addition processes

Tetrahedron Letters

Volumn 37, Issue 5, 1996, Pages 619-622

  Dyker, Gerald ^a   Grundt, Peter ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030052924     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02270-8     Document Type: Article

References (10)

1. J. B. Melpolder, R. F. Heck, J. Org. Chem. 1976, 42, 265-272.
2. A. J. Chalk, S. A. Magennis, J. Org. Chem. 1976, 41, 273-278, 1206-1209.
3. R. C. Larock, W.-Y. Leung, S. Stolz-Dunn, Tetrahedron Lett. 1989, 30, 6629-6632.
4. W. Smadja, S. Czernecki, G. Ville, C. Georgoulis, Organometallics 1987, 7, 166-169.
5. S.-K. Kang, K.-Y. Jung, C.-H. Park, E.-Y. Namkoong, Tetrahedron Lett. 1995, 36, 6287-6290.
6. Byproducts resulting from intermolecular Aldol-type condensations under similar reaction conditions have been reported: Y. Tamaru, Y. Yamada, Z.-I. Yoshida, J. Org. Chem. 1978, 43, 3396-3398; for a domino process to phthalimidines involving Heck reaction and Michael addition: N. Barr, J. P. Bartley, P. W. Clark, P. Dunstan, S. F. Dyke, J. Organomet. Chem. 1986, 302, 117-126.
7. Byproducts resulting from intermolecular Aldol-type condensations under similar reaction conditions have been reported: Y. Tamaru, Y. Yamada, Z.-I. Yoshida, J. Org. Chem. 1978, 43, 3396-3398; for a domino process to phthalimidines involving Heck reaction and Michael addition: N. Barr, J. P. Bartley, P. W. Clark, P. Dunstan, S. F. Dyke, J. Organomet. Chem. 1986, 302, 117-126.
8. For a review on sequential transformations: L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. Eng. 1993, 32, 131-163.
9. For a review on sequential transformations: L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. Eng. 1993, 32, 131-163.
10. 3, TMS): δ = 21.35 ppm (t), 28.24 (t), 30.32 (q), 35.40 (d), 47.55 (d), 48.40 (t), 124.54 (d), 125.35 (d), 126.12 (d), 126.40 (d), 126.48 (d), 127.48 (d), 127.86 (d), 128.65 (d), 128.73 (d), 129.16 (d), 130.38 (s), 132.69 (d), 134.07 (s), 135.17 (s), 135.81 (s), 140.27 (s), 206.56 (s), 207.23 (s).