On reaction of enamides with acetyl nitrate

Tetrahedron Letters

Volumn 37, Issue 12, 1996, Pages 2079-2082

  Morzycki, Jacek W ^a   Wilczewska, Agnieszka Z ^a   ŁOtowski, Zenon ^a  

^a UNIVERSITY OF BIALYSTOK   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

NITRO DERIVATIVE;

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

EID: 0029872990     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00197-9     Document Type: Article

References (22)

1. Bordwell, F. G.; Garbish, Jr., E. W. J. Am. Chem. Soc. 1960, 82, 3588.
2. Dampawan, P.; Zajac, Jr., W. W. Synthesis 1983, 545.
3. Morzycki, J. W. Polish J. Chem. 1995, 69, 321.
4. Singh, H.; Jindal, D. P.; Yadav, M. R.; Kumar, M. Prog. Med. Chem. 1991, 28, 233.
5. Bakshi, R. K.; Patel, G. F.; Rasmusson, G. H.; Baginsky, W. F.; Cimis, G.; Ellsworth, K.; Chang, B.; Bull, H.; Tolman, R. L.; Harris, G. S. J. Med Chem. 1994, 37, 3871.
6. Haffner, C. Tetrahedron Lett. 1995, 36, 4039.
7. Shoppee, C. W.; Killick, R. W.; Kruger, G. J. Chem. Soc. 1962, 2275.
8. Jacobs, T. L.; Brownfield, R. B. J. Am. Chem. Soc. 1960, 82, 4033.
9. All new compounds exhibited spectroscopic (IR, NMR and MS) and analytical (combustion analysis or high resolution mass spectrum) data in accord with the assigned structure.
10. 13C-NMR, δ 169.5, 150.9, 123.8; m/z 430 (42%), 413 (28%), 398 (38%), 395 (100), 383 (21%).
11. 7α-H 4.65 ppm). These values are most consistent with axial-equatorial and diaxial coupling, respectively. This assignment is corroborated by the down-field shift of C-19 protons in the 7β-OH epimer (δ 1.36 versus 1.30 in the 7α-OH epimer).
12. 13C-NMR, δ 169.8, 154.4, 127.1; m/z 446 (21%), 428 (100), 414 (14%), 411 (21%).
13. 13C-NMR, δ 169.5, 149.9, 135.6; m/z 460 (28%), 443 (30%), 414 (100%).
14. 13C-NMR, δ 205.4, 173.0, 85.1; m/z 417 (1%), 399 (29%), 384 (12%), 262 (64%), 127 (100).
15. 13C-NMR, δ 208.2, 171.1, 91.5; m/z 431 (<1%), 262 (5%), 141 (100%).
16. Back, T. G.; Ibrahim, N. Tetrahedron Lett. 1979, 4931.
17. Back, T. G.; Chau, J. H.-L.; Dyck, B. P.; Gladstone, P. L. Can. J. Chem. 1991, 69, 1482.
18. 13C-NMR, δ 171.9, 152.0, 123.2; m/z 430 (91%), 413 (100%), 398 (15%), 384 (46%).
19. 13C-NMR, δ 198.3, 169.5, 168.5, 97.9; m/z 461 (11%), 416 (29%), 399 (100%), 372 (99%).
20. 13C-NMR, δ 170.6, 157.6, 139.1, 124.2, 118.7; m/z 473 (100%), 458 (5%), 443 (7%), 427 (6%).
21. 13C-NMR, δ 169.6, 166.8, 149.8, 125.9, 113.8; m/z 577 (1%), 545 (1.5%), 503 (23%), 500 (28%), 487 (100%), 458 (36%).
22. Molecular modeling was performed with HyperChem ™ Release 3 from Hypercube, Inc. Minimizations employed the MM+ force field and the Polak-Ribiere (conjugate gradient) algorithm.