Fused-ring nitrogen and sulfur heterocycles by a tandem SN2-Michael addition reaction

Journal of Heterocyclic Chemistry

Volumn 39, Issue 5, 2002, Pages 1049-1054

  Bunce, Richard A ^a   Kotturi, Sharadsrikar V ^a   Peeples, Christopher J ^a   Holt, Elizabeth M ^a  

^a OKLAHOMA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ACRYLIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; NITROGEN; SULFUR;

ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; CYCLIZATION; ISOMER; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0036745999     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570390531     Document Type: Article

References (46)

1. R. A. Bunce, C. J. Peeples and P. B. Jones, J. Org. Chem., 57, 1727 (1992).
2. [a] A. R. Pinder, Nat. Prod. Reports, 1, 225 (1984);
3. [b] A. R. Pinder, Nat. Prod. Reports, 3, 171 (1986);
4. [c] A. R. Pinder, Nat. Prod. Reports, 4, 527 (1987);
5. [d] A. R. Pinder, Nat. Prod. Reports, 6, 67 (1989);
6. [e] A. O. Plunkett, Nat. Prod. Reports, 11, 581 (1994).
7. Simlpe N heterocyclic ketones: [a] J. C. Craig, S.-Y. C. Lee and S. K. Roy, J. Org. Chem., 43, 347 (1978); [b] I. R. C. Bick, J. W. Gillard and H.-M. Leow, Aust. J. Chem., 32, 2523 (1979); [c] C. E. Turner, M. A. Elsohly, L. Hanus and H. N. Elsohly, Phytochemistry, 20, 1403 (1981); [d] J. A. Lamberton, Y. A. Geewananda, P. Gunawardana and I. R. C. Bick, J. Nat. Prod., 46, 235 (1983); [e] D. H. G. Medina, M. Pusset, J. Pusset and H.-P. Husson, J. Nat. Prod., 46, 398 (1983); [f] T. Langenskïld and M. Lounasmaa, Heterocycles, 20, 671 (1983); [g] R. Ghirlando, A. S. Howard, R. B. Katz and J. P. Michael, Tetrahedron, 40, 2879 (1984); [h] K. Irie, K. Aoe, T. Tanaka and S. Saito, J. Chem. Soc. Chem. Commun., 633 (1985); [i] J. J. Tufariello and J. M. Puglis, Tetrahedron Lett., 27, 1265 (1986); [j] J. F. Stevens, H. Hart, H. Hendriks and T. M. Malingŕ, Phytochemistry, 31, 3917 (1992); [k] H. Neuhoefer, L. Witte, M. Gorunovic and F. C. Czygan, Pharmazie, 48, 389 (1993); [l] J. H. Kim, H. Hart and J. F. Stevens, Phytochemistry, 41, 1319 (1996); [m] A. B. Pomilio, M. D. Gonźlez and C. C. Eceizabarrena, Phytochemistry, 41, 1393 (1996).
8. Simpe N heterocyclic ketones: [a] J. C. Craig, S.-Y. C. Lee and S. K. Roy, J. Org. Chem., 43, 347 (1978); [b] I. R. C. Bick, J. W. Gillard and H.-M. Leow, Aust. J. Chem., 32, 2523 (1979); [c] C. E. Turner, M. A. Elsohly, L. Hanus and H. N. Elsohly, Phytochemistry, 20, 1403 (1981); [d] J. A. Lamberton, Y. A. Geewananda, P. Gunawardana and I. R. C. Bick, J. Nat. Prod., 46, 235 (1983); [e] D. H. G. Medina, M. Pusset, J. Pusset and H.-P. Husson, J. Nat. Prod., 46, 398 (1983); [f] T. Langenskïld and M. Lounasmaa, Heterocycles, 20, 671 (1983); [g] R. Ghirlando, A. S. Howard, R. B. Katz and J. P. Michael, Tetrahedron, 40, 2879 (1984); [h] K. Irie, K. Aoe, T. Tanaka and S. Saito, J. Chem. Soc. Chem. Commun., 633 (1985); [i] J. J. Tufariello and J. M. Puglis, Tetrahedron Lett., 27, 1265 (1986); [j] J. F. Stevens, H. Hart, H. Hendriks and T. M. Malingŕ, Phytochemistry, 31, 3917 (1992); [k] H. Neuhoefer, L. Witte, M. Gorunovic and F. C. Czygan, Pharmazie, 48, 389 (1993); [l] J. H. Kim, H. Hart and J. F. Stevens, Phytochemistry, 41, 1319 (1996); [m] A. B. Pomilio, M. D. Gonźlez and C. C. Eceizabarrena, Phytochemistry, 41, 1393 (1996).
9. Simpe N heterocyclic ketones: [a] J. C. Craig, S.-Y. C. Lee and S. K. Roy, J. Org. Chem., 43, 347 (1978); [b] I. R. C. Bick, J. W. Gillard and H.-M. Leow, Aust. J. Chem., 32, 2523 (1979); [c] C. E. Turner, M. A. Elsohly, L. Hanus and H. N. Elsohly, Phytochemistry, 20, 1403 (1981); [d] J. A. Lamberton, Y. A. Geewananda, P. Gunawardana and I. R. C. Bick, J. Nat. Prod., 46, 235 (1983); [e] D. H. G. Medina, M. Pusset, J. Pusset and H.-P. Husson, J. Nat. Prod., 46, 398 (1983); [f] T. Langenskïld and M. Lounasmaa, Heterocycles, 20, 671 (1983); [g] R. Ghirlando, A. S. Howard, R. B. Katz and J. P. Michael, Tetrahedron, 40, 2879 (1984); [h] K. Irie, K. Aoe, T. Tanaka and S. Saito, J. Chem. Soc. Chem. Commun., 633 (1985); [i] J. J. Tufariello and J. M. Puglis, Tetrahedron Lett., 27, 1265 (1986); [j] J. F. Stevens, H. Hart, H. Hendriks and T. M. Malingŕ, Phytochemistry, 31, 3917 (1992); [k] H. Neuhoefer, L. Witte, M. Gorunovic and F. C. Czygan, Pharmazie, 48, 389 (1993); [l] J. H. Kim, H. Hart and J. F. Stevens, Phytochemistry, 41, 1319 (1996); [m] A. B. Pomilio, M. D. Gonźlez and C. C. Eceizabarrena, Phytochemistry, 41, 1393 (1996).
10. Simpe N heterocyclic ketones: [a] J. C. Craig, S.-Y. C. Lee and S. K. Roy, J. Org. Chem., 43, 347 (1978); [b] I. R. C. Bick, J. W. Gillard and H.-M. Leow, Aust. J. Chem., 32, 2523 (1979); [c] C. E. Turner, M. A. Elsohly, L. Hanus and H. N. Elsohly, Phytochemistry, 20, 1403 (1981); [d] J. A. Lamberton, Y. A. Geewananda, P. Gunawardana and I. R. C. Bick, J. Nat. Prod., 46, 235 (1983); [e] D. H. G. Medina, M. Pusset, J. Pusset and H.-P. Husson, J. Nat. Prod., 46, 398 (1983); [f] T. Langenskïld and M. Lounasmaa, Heterocycles, 20, 671 (1983); [g] R. Ghirlando, A. S. Howard, R. B. Katz and J. P. Michael, Tetrahedron, 40, 2879 (1984); [h] K. Irie, K. Aoe, T. Tanaka and S. Saito, J. Chem. Soc. Chem. Commun., 633 (1985); [i] J. J. Tufariello and J. M. Puglis, Tetrahedron Lett., 27, 1265 (1986); [j] J. F. Stevens, H. Hart, H. Hendriks and T. M. Malingŕ, Phytochemistry, 31, 3917 (1992); [k] H. Neuhoefer, L. Witte, M. Gorunovic and F. C. Czygan, Pharmazie, 48, 389 (1993); [l] J. H. Kim, H. Hart and J. F. Stevens, Phytochemistry, 41, 1319 (1996); [m] A. B. Pomilio, M. D. Gonźlez and C. C. Eceizabarrena, Phytochemistry, 41, 1393 (1996).
11. Simpe N heterocyclic ketones: [a] J. C. Craig, S.-Y. C. Lee and S. K. Roy, J. Org. Chem., 43, 347 (1978); [b] I. R. C. Bick, J. W. Gillard and H.-M. Leow, Aust. J. Chem., 32, 2523 (1979); [c] C. E. Turner, M. A. Elsohly, L. Hanus and H. N. Elsohly, Phytochemistry, 20, 1403 (1981); [d] J. A. Lamberton, Y. A. Geewananda, P. Gunawardana and I. R. C. Bick, J. Nat. Prod., 46, 235 (1983); [e] D. H. G. Medina, M. Pusset, J. Pusset and H.-P. Husson, J. Nat. Prod., 46, 398 (1983); [f] T. Langenskïld and M. Lounasmaa, Heterocycles, 20, 671 (1983); [g] R. Ghirlando, A. S. Howard, R. B. Katz and J. P. Michael, Tetrahedron, 40, 2879 (1984); [h] K. Irie, K. Aoe, T. Tanaka and S. Saito, J. Chem. Soc. Chem. Commun., 633 (1985); [i] J. J. Tufariello and J. M. Puglis, Tetrahedron Lett., 27, 1265 (1986); [j] J. F. Stevens, H. Hart, H. Hendriks and T. M. Malingŕ, Phytochemistry, 31, 3917 (1992); [k] H. Neuhoefer, L. Witte, M. Gorunovic and F. C. Czygan, Pharmazie, 48, 389 (1993); [l] J. H. Kim, H. Hart and J. F. Stevens, Phytochemistry, 41, 1319 (1996); [m] A. B. Pomilio, M. D. Gonźlez and C. C. Eceizabarrena, Phytochemistry, 41, 1393 (1996).
12. Simpe N heterocyclic ketones: [a] J. C. Craig, S.-Y. C. Lee and S. K. Roy, J. Org. Chem., 43, 347 (1978); [b] I. R. C. Bick, J. W. Gillard and H.-M. Leow, Aust. J. Chem., 32, 2523 (1979); [c] C. E. Turner, M. A. Elsohly, L. Hanus and H. N. Elsohly, Phytochemistry, 20, 1403 (1981); [d] J. A. Lamberton, Y. A. Geewananda, P. Gunawardana and I. R. C. Bick, J. Nat. Prod., 46, 235 (1983); [e] D. H. G. Medina, M. Pusset, J. Pusset and H.-P. Husson, J. Nat. Prod., 46, 398 (1983); [f] T. Langenskïld and M. Lounasmaa, Heterocycles, 20, 671 (1983); [g] R. Ghirlando, A. S. Howard, R. B. Katz and J. P. Michael, Tetrahedron, 40, 2879 (1984); [h] K. Irie, K. Aoe, T. Tanaka and S. Saito, J. Chem. Soc. Chem. Commun., 633 (1985); [i] J. J. Tufariello and J. M. Puglis, Tetrahedron Lett., 27, 1265 (1986); [j] J. F. Stevens, H. Hart, H. Hendriks and T. M. Malingŕ, Phytochemistry, 31, 3917 (1992); [k] H. Neuhoefer, L. Witte, M. Gorunovic and F. C. Czygan, Pharmazie, 48, 389 (1993); [l] J. H. Kim, H. Hart and J. F. Stevens, Phytochemistry, 41, 1319 (1996); [m] A. B. Pomilio, M. D. Gonźlez and C. C. Eceizabarrena, Phytochemistry, 41, 1393 (1996).
13. Simpe N heterocyclic ketones: [a] J. C. Craig, S.-Y. C. Lee and S. K. Roy, J. Org. Chem., 43, 347 (1978); [b] I. R. C. Bick, J. W. Gillard and H.-M. Leow, Aust. J. Chem., 32, 2523 (1979); [c] C. E. Turner, M. A. Elsohly, L. Hanus and H. N. Elsohly, Phytochemistry, 20, 1403 (1981); [d] J. A. Lamberton, Y. A. Geewananda, P. Gunawardana and I. R. C. Bick, J. Nat. Prod., 46, 235 (1983); [e] D. H. G. Medina, M. Pusset, J. Pusset and H.-P. Husson, J. Nat. Prod., 46, 398 (1983); [f] T. Langenskïld and M. Lounasmaa, Heterocycles, 20, 671 (1983); [g] R. Ghirlando, A. S. Howard, R. B. Katz and J. P. Michael, Tetrahedron, 40, 2879 (1984); [h] K. Irie, K. Aoe, T. Tanaka and S. Saito, J. Chem. Soc. Chem. Commun., 633 (1985); [i] J. J. Tufariello and J. M. Puglis, Tetrahedron Lett., 27, 1265 (1986); [j] J. F. Stevens, H. Hart, H. Hendriks and T. M. Malingŕ, Phytochemistry, 31, 3917 (1992); [k] H. Neuhoefer, L. Witte, M. Gorunovic and F. C. Czygan, Pharmazie, 48, 389 (1993); [l] J. H. Kim, H. Hart and J. F. Stevens, Phytochemistry, 41, 1319 (1996); [m] A. B. Pomilio, M. D. Gonźlez and C. C. Eceizabarrena, Phytochemistry, 41, 1393 (1996).
14. Simpe N heterocyclic ketones: [a] J. C. Craig, S.-Y. C. Lee and S. K. Roy, J. Org. Chem., 43, 347 (1978); [b] I. R. C. Bick, J. W. Gillard and H.-M. Leow, Aust. J. Chem., 32, 2523 (1979); [c] C. E. Turner, M. A. Elsohly, L. Hanus and H. N. Elsohly, Phytochemistry, 20, 1403 (1981); [d] J. A. Lamberton, Y. A. Geewananda, P. Gunawardana and I. R. C. Bick, J. Nat. Prod., 46, 235 (1983); [e] D. H. G. Medina, M. Pusset, J. Pusset and H.-P. Husson, J. Nat. Prod., 46, 398 (1983); [f] T. Langenskïld and M. Lounasmaa, Heterocycles, 20, 671 (1983); [g] R. Ghirlando, A. S. Howard, R. B. Katz and J. P. Michael, Tetrahedron, 40, 2879 (1984); [h] K. Irie, K. Aoe, T. Tanaka and S. Saito, J. Chem. Soc. Chem. Commun., 633 (1985); [i] J. J. Tufariello and J. M. Puglis, Tetrahedron Lett., 27, 1265 (1986); [j] J. F. Stevens, H. Hart, H. Hendriks and T. M. Malingŕ, Phytochemistry, 31, 3917 (1992); [k] H. Neuhoefer, L. Witte, M. Gorunovic and F. C. Czygan, Pharmazie, 48, 389 (1993); [l] J. H. Kim, H. Hart and J. F. Stevens, Phytochemistry, 41, 1319 (1996); [m] A. B. Pomilio, M. D. Gonźlez and C. C. Eceizabarrena, Phytochemistry, 41, 1393 (1996).
15. Simpe N heterocyclic ketones: [a] J. C. Craig, S.-Y. C. Lee and S. K. Roy, J. Org. Chem., 43, 347 (1978); [b] I. R. C. Bick, J. W. Gillard and H.-M. Leow, Aust. J. Chem., 32, 2523 (1979); [c] C. E. Turner, M. A. Elsohly, L. Hanus and H. N. Elsohly, Phytochemistry, 20, 1403 (1981); [d] J. A. Lamberton, Y. A. Geewananda, P. Gunawardana and I. R. C. Bick, J. Nat. Prod., 46, 235 (1983); [e] D. H. G. Medina, M. Pusset, J. Pusset and H.-P. Husson, J. Nat. Prod., 46, 398 (1983); [f] T. Langenskïld and M. Lounasmaa, Heterocycles, 20, 671 (1983); [g] R. Ghirlando, A. S. Howard, R. B. Katz and J. P. Michael, Tetrahedron, 40, 2879 (1984); [h] K. Irie, K. Aoe, T. Tanaka and S. Saito, J. Chem. Soc. Chem. Commun., 633 (1985); [i] J. J. Tufariello and J. M. Puglis, Tetrahedron Lett., 27, 1265 (1986); [j] J. F. Stevens, H. Hart, H. Hendriks and T. M. Malingŕ, Phytochemistry, 31, 3917 (1992); [k] H. Neuhoefer, L. Witte, M. Gorunovic and F. C. Czygan, Pharmazie, 48, 389 (1993); [l] J. H. Kim, H. Hart and J. F. Stevens, Phytochemistry, 41, 1319 (1996); [m] A. B. Pomilio, M. D. Gonźlez and C. C. Eceizabarrena, Phytochemistry, 41, 1393 (1996).
16. Simpe N heterocyclic ketones: [a] J. C. Craig, S.-Y. C. Lee and S. K. Roy, J. Org. Chem., 43, 347 (1978); [b] I. R. C. Bick, J. W. Gillard and H.-M. Leow, Aust. J. Chem., 32, 2523 (1979); [c] C. E. Turner, M. A. Elsohly, L. Hanus and H. N. Elsohly, Phytochemistry, 20, 1403 (1981); [d] J. A. Lamberton, Y. A. Geewananda, P. Gunawardana and I. R. C. Bick, J. Nat. Prod., 46, 235 (1983); [e] D. H. G. Medina, M. Pusset, J. Pusset and H.-P. Husson, J. Nat. Prod., 46, 398 (1983); [f] T. Langenskïld and M. Lounasmaa, Heterocycles, 20, 671 (1983); [g] R. Ghirlando, A. S. Howard, R. B. Katz and J. P. Michael, Tetrahedron, 40, 2879 (1984); [h] K. Irie, K. Aoe, T. Tanaka and S. Saito, J. Chem. Soc. Chem. Commun., 633 (1985); [i] J. J. Tufariello and J. M. Puglis, Tetrahedron Lett., 27, 1265 (1986); [j] J. F. Stevens, H. Hart, H. Hendriks and T. M. Malingŕ, Phytochemistry, 31, 3917 (1992); [k] H. Neuhoefer, L. Witte, M. Gorunovic and F. C. Czygan, Pharmazie, 48, 389 (1993); [l] J. H. Kim, H. Hart and J. F. Stevens, Phytochemistry, 41, 1319 (1996); [m] A. B. Pomilio, M. D. Gonźlez and C. C. Eceizabarrena, Phytochemistry, 41, 1393 (1996).
17. Simpe N heterocyclic ketones: [a] J. C. Craig, S.-Y. C. Lee and S. K. Roy, J. Org. Chem., 43, 347 (1978); [b] I. R. C. Bick, J. W. Gillard and H.-M. Leow, Aust. J. Chem., 32, 2523 (1979); [c] C. E. Turner, M. A. Elsohly, L. Hanus and H. N. Elsohly, Phytochemistry, 20, 1403 (1981); [d] J. A. Lamberton, Y. A. Geewananda, P. Gunawardana and I. R. C. Bick, J. Nat. Prod., 46, 235 (1983); [e] D. H. G. Medina, M. Pusset, J. Pusset and H.-P. Husson, J. Nat. Prod., 46, 398 (1983); [f] T. Langenskïld and M. Lounasmaa, Heterocycles, 20, 671 (1983); [g] R. Ghirlando, A. S. Howard, R. B. Katz and J. P. Michael, Tetrahedron, 40, 2879 (1984); [h] K. Irie, K. Aoe, T. Tanaka and S. Saito, J. Chem. Soc. Chem. Commun., 633 (1985); [i] J. J. Tufariello and J. M. Puglis, Tetrahedron Lett., 27, 1265 (1986); [j] J. F. Stevens, H. Hart, H. Hendriks and T. M. Malingŕ, Phytochemistry, 31, 3917 (1992); [k] H. Neuhoefer, L. Witte, M. Gorunovic and F. C. Czygan, Pharmazie, 48, 389 (1993); [l] J. H. Kim, H. Hart and J. F. Stevens, Phytochemistry, 41, 1319 (1996); [m] A. B. Pomilio, M. D. Gonźlez and C. C. Eceizabarrena, Phytochemistry, 41, 1393 (1996).
18. Simpe N heterocyclic ketones: [a] J. C. Craig, S.-Y. C. Lee and S. K. Roy, J. Org. Chem., 43, 347 (1978); [b] I. R. C. Bick, J. W. Gillard and H.-M. Leow, Aust. J. Chem., 32, 2523 (1979); [c] C. E. Turner, M. A. Elsohly, L. Hanus and H. N. Elsohly, Phytochemistry, 20, 1403 (1981); [d] J. A. Lamberton, Y. A. Geewananda, P. Gunawardana and I. R. C. Bick, J. Nat. Prod., 46, 235 (1983); [e] D. H. G. Medina, M. Pusset, J. Pusset and H.-P. Husson, J. Nat. Prod., 46, 398 (1983); [f] T. Langenskïld and M. Lounasmaa, Heterocycles, 20, 671 (1983); [g] R. Ghirlando, A. S. Howard, R. B. Katz and J. P. Michael, Tetrahedron, 40, 2879 (1984); [h] K. Irie, K. Aoe, T. Tanaka and S. Saito, J. Chem. Soc. Chem. Commun., 633 (1985); [i] J. J. Tufariello and J. M. Puglis, Tetrahedron Lett., 27, 1265 (1986); [j] J. F. Stevens, H. Hart, H. Hendriks and T. M. Malingŕ, Phytochemistry, 31, 3917 (1992); [k] H. Neuhoefer, L. Witte, M. Gorunovic and F. C. Czygan, Pharmazie, 48, 389 (1993); [l] J. H. Kim, H. Hart and J. F. Stevens, Phytochemistry, 41, 1319 (1996); [m] A. B. Pomilio, M. D. Gonźlez and C. C. Eceizabarrena, Phytochemistry, 41, 1393 (1996).
19. Simpe N heterocyclic ketones: [a] J. C. Craig, S.-Y. C. Lee and S. K. Roy, J. Org. Chem., 43, 347 (1978); [b] I. R. C. Bick, J. W. Gillard and H.-M. Leow, Aust. J. Chem., 32, 2523 (1979); [c] C. E. Turner, M. A. Elsohly, L. Hanus and H. N. Elsohly, Phytochemistry, 20, 1403 (1981); [d] J. A. Lamberton, Y. A. Geewananda, P. Gunawardana and I. R. C. Bick, J. Nat. Prod., 46, 235 (1983); [e] D. H. G. Medina, M. Pusset, J. Pusset and H.-P. Husson, J. Nat. Prod., 46, 398 (1983); [f] T. Langenskïld and M. Lounasmaa, Heterocycles, 20, 671 (1983); [g] R. Ghirlando, A. S. Howard, R. B. Katz and J. P. Michael, Tetrahedron, 40, 2879 (1984); [h] K. Irie, K. Aoe, T. Tanaka and S. Saito, J. Chem. Soc. Chem. Commun., 633 (1985); [i] J. J. Tufariello and J. M. Puglis, Tetrahedron Lett., 27, 1265 (1986); [j] J. F. Stevens, H. Hart, H. Hendriks and T. M. Malingŕ, Phytochemistry, 31, 3917 (1992); [k] H. Neuhoefer, L. Witte, M. Gorunovic and F. C. Czygan, Pharmazie, 48, 389 (1993); [l] J. H. Kim, H. Hart and J. F. Stevens, Phytochemistry, 41, 1319 (1996); [m] A. B. Pomilio, M. D. Gonźlez and C. C. Eceizabarrena, Phytochemistry, 41, 1393 (1996).
20. Simple N, O and S heterocyclic esters: [a] I. Felner-Caboga and K. Schenker, German Patent 2,100,422 (1971); Chem. Abstr., 75, 129657x (1971); [b] E. Vedejs, M. J. Mullins, J. M. Renga and S. P. Singer, Tetrahedron Lett., 519 (1978); [c] T. Nikiforov, S. Stanchev, B. Milenkov and V. Dimitrov, Synth. Commun., 20, 1977 (1990); [d] R. A. Bunce and M. J. Bennett, Synth. Commun., 23, 1009 (1993).
21. Simple N, O and S heterocyclic esters: [a] I. Felner-Caboga and K. Schenker, German Patent 2,100,422 (1971); Chem. Abstr., 75, 129657x (1971); [b] E. Vedejs, M. J. Mullins, J. M. Renga and S. P. Singer, Tetrahedron Lett., 519 (1978); [c] T. Nikiforov, S. Stanchev, B. Milenkov and V. Dimitrov, Synth. Commun., 20, 1977 (1990); [d] R. A. Bunce and M. J. Bennett, Synth. Commun., 23, 1009 (1993).
22. Simple N, O and S heterocyclic esters: [a] I. Felner-Caboga and K. Schenker, German Patent 2,100,422 (1971); Chem. Abstr., 75, 129657x (1971); [b] E. Vedejs, M. J. Mullins, J. M. Renga and S. P. Singer, Tetrahedron Lett., 519 (1978); [c] T. Nikiforov, S. Stanchev, B. Milenkov and V. Dimitrov, Synth. Commun., 20, 1977 (1990); [d] R. A. Bunce and M. J. Bennett, Synth. Commun., 23, 1009 (1993).
23. Simple N, O and S heterocyclic esters: [a] I. Felner-Caboga and K. Schenker, German Patent 2,100,422 (1971); Chem. Abstr., 75, 129657x (1971); [b] E. Vedejs, M. J. Mullins, J. M. Renga and S. P. Singer, Tetrahedron Lett., 519 (1978); [c] T. Nikiforov, S. Stanchev, B. Milenkov and V. Dimitrov, Synth. Commun., 20, 1977 (1990); [d] R. A. Bunce and M. J. Bennett, Synth. Commun., 23, 1009 (1993).
24. Fused-ring N heterocycles: [a] C. J. Blankley, European Patent 58,567 (1982); Chem. Abstr., 98, 54484c (1983); [b] R. K. Boeckman, Jr., J. P. Sabatucci, S. W. Goldstein, D. M. Springer and P. E Jackson, J. Org. Chem., 51, 3740 (1986); [c] J. D. Elliott, R. G. Franz, M. A. Lago and A. Gao, U.S Patent 5,736,564 (1998); Chem. Abstr., 128, 270534z (1998); See ref. 2a.
25. Fused-ring N heterocycles: [a] C. J. Blankley, European Patent 58,567 (1982); Chem. Abstr., 98, 54484c (1983); [b] R. K. Boeckman, Jr., J. P. Sabatucci, S. W. Goldstein, D. M. Springer and P. E Jackson, J. Org. Chem., 51, 3740 (1986); [c] J. D. Elliott, R. G. Franz, M. A. Lago and A. Gao, U.S Patent 5,736,564 (1998); Chem. Abstr., 128, 270534z (1998); See ref. 2a.
26. Fused-ring N heterocycles: [a] C. J. Blankley, European Patent 58,567 (1982); Chem. Abstr., 98, 54484c (1983); [b] R. K. Boeckman, Jr., J. P. Sabatucci, S. W. Goldstein, D. M. Springer and P. E Jackson, J. Org. Chem., 51, 3740 (1986); [c] J. D. Elliott, R. G. Franz, M. A. Lago and A. Gao, U.S Patent 5,736,564 (1998); Chem. Abstr., 128, 270534z (1998); See ref. 2a.
27. Fused-ring N heterocycles: [a] C. J. Blankley, European Patent 58,567 (1982); Chem. Abstr., 98, 54484c (1983); [b] R. K. Boeckman, Jr., J. P. Sabatucci, S. W. Goldstein, D. M. Springer and P. E Jackson, J. Org. Chem., 51, 3740 (1986); [c] J. D. Elliott, R. G. Franz, M. A. Lago and A. Gao, U.S Patent 5,736,564 (1998); Chem. Abstr., 128, 270534z (1998); See ref. 2a.
28. J. M. Photis and L. A. Paquette, Organic Syntheses, Wiley: New York, NY, Coll. Vol. VI, 1988, pp 482-488.
29. The trans-1,2-cyclohexanedimethanol was prepared from diethyl trans-1,2,3,6-tetrahydrophthalate by (1) hydrogenation over 5% palladium-on-carbon followed by (2) reduction with lithium aluminum hydride. Diethyl trans-1,2,3,6-tetrahydrophthalate was prepared using the method described in T. E. Sample, Jr. and L. F. Hatch, Organic Syntheses, Wiley, New York, NY, Coll. Vol. VI, 1988, pp 454-458.
30. E. J. Corey and A. Palani, Tetrahedron Lett., 36, 3485 (1995).
31. D. B. Dess and J. C. Martin, J. Am. Chem. Soc., 113, 7277 (1991).
32. A. Maercker, Org. React., 14, 270 (1965).
33. R. K. Crossland and K. L. Servis, J. Org. Chem., 35, 3195 (1970).
34. A. J. Speziale, Organic Syntheses, Wiley, New York, NY, Coll. Vol. IV, 1963, pp 401-403.
35. J. E. Baldwin, J. Chem. Soc., Chem. Commun., 734 (1976).
36. [a] A. E. Derome, Modem NMR Techniques for Chemistry Research, Elsevier Science, New York, NY, 1987, pp 227-230;
37. [b] T. D. W. Claridge, High-Resolution NMR Techniques in Organic Chemistry, Elsevier Science, New York, NY, 1999, pp 158, 188 and 197-199.
38. D. Neuhaus, M. P. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, VCH, New York, NY, 1989, pp 253-306.
39. [a] D. N. Brattesani and C. H. Heathcock, J. Org. Chem., 40, 2165 (1975);
40. [b] C. H. Heathcock, K. M. Smith and T. A. Blumenkopf, J. Am. Chem. Soc., 108, 5022 (1986);
41. [c] B. Chenera, C.-P. Chuang, D. J. Hart and C.-S. Lai, J. Org. Chem., 57, 2018 (1992);
42. [d] R. A. Bunce and C. R. Harris, Synth. Commun., 26, 1969 (1996).
43. W. C. Stille, M. Kahn and A. Mitra, J. Org. Chem., 43, 2923 (1978).
44. XSCANS Users Manual; Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA (1991).
45. G. M. Sheldrick, Acta Cryst., A46, 467 (1990).
46. G. M. Sheldrick, SHELXL97 Program for the Refinement of Crystal Structures; University of Gottingen, Germany (1997).