Reactions of α,β-unsaturated thioamides with diazo compounds

Helvetica Chimica Acta

Volumn 89, Issue 11, 2006, Pages 2815-2824

  Egli, Daniel H ^a   Linden, Anthony ^a   Heimgartner, Heinz ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTALLINE PRODUCTS; DERIVATIZATION; MONOSUBSTITUTED THIOAMIDE; REGIOISOMERS;

ADDITION REACTIONS; ISOMERS; REACTION KINETICS; SATURATION (MATERIALS COMPOSITION); X RAY CRYSTALLOGRAPHY;

NITROGEN COMPOUNDS;

1 (2 CHLOROBENZOYL) N,N DIETHYL 4,5 DIHYDRO 4 METHYL 3 PHENYL 1H PYRAZOLE 5 CARBOTHIOAMIDE; 1 (2 CHLOROBENZOYL) N,N DIETHYL 4,5 DIHYDRO 4 METHYL 5 PHENYL 1H PYRAZOLE 3 CARBOTHIOAMIDE; 2 CHLOROBENZOYL CHLORIDE; 4,5 DIHYDRO 1H PYRAZOLE 3 CARBOTHIOAMIDE; AZO COMPOUND; BENZENE DERIVATIVE; DIAZOACETIC ACID ETHYL ESTER; DIAZOCYCLOHEXANE; ETHYL 4 (DIETHYLTHIOCARBAMOYL) 4,5 DIHYDRO 5 METHYL 1H PYRAZOLE 3 CARBOXYLATE; N METHYLPROP 2 ENETHIOAMIDE; N,N DIETHYL 4 METHYL 1,2 DIAZASPIRO[4.5]DEC 2 ENE 3 CARBOTHIOAMIDE; N,N DIETHYL 4,5 DIHYDRO 4 METHYL 1H PYRAZOLE 3 CARBOTHIOAMIDE; N,N DIETHYL 4,5 DIHYDRO 4 METHYL 3 PHENYL 1H PYRAZOLE 5 CARBOTHIOAMIDE; N,N DIETHYL 4,5 DIHYDRO 4 METHYL 3H PYRAZOLE 3 CARBOTHIOAMIDE; N,N DIETHYL 4,5 DIHYDRO 4 METHYL 5 PHENYL 1H PYRAZOLE 3 CARBOTHIOAMIDE; PHENYLDIAZOMETHANE; THIOAMIDE;

AMINO TERMINAL SEQUENCE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLOADDITION; DERIVATIZATION; DIPOLE; INFRARED SPECTROSCOPY; ISOMERISM; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 33845367553     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200690252     Document Type: Article

References (31)

1. G. Mlostoń, H. Heimgartner, Pol. J. Chem. 2000, 74, 1503.
2. G. Mlostoń, H. Heimgartner, in 'The Chemistry of Heterocyclic Compounds, Vol. 59, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products', Eds. A. Padwa and W. H. Pearson, John Wiley & Sons, New York, 2002, p. 315.
3. R. Huisgen, E. Langhals, Tetrahedron Lett. 1989, 30, 5369;
4. R. Huisgen, L. Fišera, H. Giera, R. Sustmann, J. Am. Chem. Soc. 1995, 117, 9671;
5. R. Huisgen, X. Li, H. Giera, E. Langhals, Helv. Chim. Acta 2001, 84, 981.
6. R. Huisgen, E. Langhals, Heteroatom Chem. 2006, 17, 433.
7. R. Sustmann, Pure Appl. Chem. 1974, 40, 569.
8. J. Geittner, R. Huisgen, R. Sustmann, Tetrahedron Lett. 1977, 10, 881.
9. A. M. S. El-Sharif, R. Ketcham, E. Schaumann, Phosphorus, Sulfur Silicon Relat. Elem. 1989, 46, 83.
10. M. Kägi, A. Linden, G. Mlostoń, H. Heimgartner, Helv. Chim. Acta 1998, 81, 285.
11. B. Kelmendi, G. Mloston, H. Heimgartner, Heterocycles 2000, 52, 475.
12. D. H. Egli, A. Linden, H. Heimgartner, Helv. Chim. Acta 2006, 89, 1910.
13. D. H. Egli, A. Linden, H. Heimgartner, Helv. Chim. Acta 2006, in press.
14. H. Alper, D. A. Brandes, Organometallics 1991, 10, 2457.
15. C. K. Johnson, ORTEPII, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
16. F. Arndt, Org. Synth. 1935, 15, 3.
17. T. L. Holton, H. Shechter, J. Org. Chem. 1995, 60, 4725.
18. D. S. Wulfman, S. Yousefian, J. M. White, Synth. Commun. 1988, 18, 2349.
19. Y. Tamura, M. Kagotani, Z. Yoshida, Tetrahedron Lett. 1981, 22, 3409.
20. R. Hooft, KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
21. Z. Otwinowski, W. Minor, in 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallography', Part A, Eds. C. W. Carter Jr., R. M. Sweet, Academic Press, New York, 1997, p. 307.
22. R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33.
23. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435.
24. H. D. Flack, G. Bernardinelli, Acta Crystallogr., Sect. A 1999, 55, 908;
25. H. D. Flack, G. Bernardinelli, J. Appl. Crystallogr. 2000, 33, 1143.
26. a) E. N. Maslen, A. G. Fox, M. A. O'Keefe, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C, Table 6.1.1.1, p. 477;
27. b) D. C. Creagh, W. J. McAuley, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C, Table 4.2.6.8, p. 219;
28. c) D. C. Creagh, J. H. Hubbell, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C, Table 4.2.4.3, p. 200.
29. R. F. Stewart, E. R. Davidson, W. T. Simpson, J. Chem. Phys. 1965, 42, 3175.
30. J. A. Ibers, W. C. Hamilton, Acta Crystallogr. 1964, 17, 781.
31. G. M. Sheldrick, SHELXL97, Program for the Refinement of Crystal Structures, University of Göttigen, Germany, 1997.