1,3-Dipolar cycloaddition reactions of organic azides with morpholinobuta-1,3-dienes and with an α-ethynyl-enamine

Helvetica Chimica Acta

Volumn 88, Issue 7, 2005, Pages 1813-1825

  Brunner, Martina ^a   Maas, Gerhard ^a   Klärner, Frank Gerrit ^b  

^a UNIVERSITY OF ULM   (Germany)

^b UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PRESSURE EFFECTS; REACTION KINETICS; SUBSTITUTION REACTIONS;

CYCLOADDITION REACTIONS; ELECTROPHILIC AZIDES; ENAMINES; ORGANIC AZIDES;

NITROGEN COMPOUNDS;

1 AMINO 1,3 DIENE; 1 PHENYL 5 (PHENYLETHYNYL) 1H 1,2,3 TRIAZOLE; 1,3 BUTADIENE; 2 AMINO 1,3 DIENE; 2 AMINOBUT 1 EN 3 YNE; 2 MORPHOLINOBUTA 1,3 DIENE; 4 (1 METHYLENE 3 PHENYLPROP 2 YNYL)MORPHOLINE; 4 (1 MORPHOLINO 2 PHENYLETHENYL) 1H 1,2,3 TRIAZOLE; 4,5 DIHYDRO 5 MORPHOLINO 1H 1,2,3 TRIAZOLE DERIVATIVE; 5 (2 PHENOXY 2 PHENYLETHENYL) 1H 1,2,3 TRIAZOLE; AZIDE; ENAMINE; MORPHOLINE DERIVATIVE; PHENOL; TERT BUTYL ALCOHOL; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATION; CYCLOADDITION; HYPERBARISM; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 23044442704     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200590142     Document Type: Article

References (37)

1. W. Lwowski, in '1,3-Dipolar Cycloaddition Chemistry', Ed. A. Padwa, Wiley, New York 1984, Vol. 1, p. 559.
2. H. Wamhoff, in 'Comprehensive Heterocyclic Chemistry', Eds. A. R. Katritzky, and C. W. Rees, Pergamon Press, Oxford, 1984, Vol. 5, p. 669.
3. R. Huisgen, G. Szeimies, L. Möbius, Chem. Ber. 1966, 99, 475;
4. G. Szeimies, R. Huisgen, Chem. Ber. 1966, 99, 491.
5. G. Himbert, M. Regitz, Chem. Ber. 1972, 100, 2975;
6. G. Himbert, M. Regitz, Liebigs Ann. Chem. 1973, 1505.
7. C. K. Sha, A. K. Mohanakrishnan, in 'Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products', Eds. A. Padwa, and W. Pearson, Wiley, New York, 2002, p. 623.
8. R. Huisgen, G. Szeimies, L. Möbius, Chem. Ber. 1967, 100, 2494.
9. R. Huisgen, in '1,3-Dipolar Cycloaddition Chemistry', Ed. A. Padwa, Wiley, New York, 1984, Vol. 1, p. 1.
10. R. Sustmann, H. Trill, Angew. Chem., Int. Ed. 1972, 11, 838.
11. R. Fusco, G. Bianchetti, D. Pocar, Gazz. Chim. Ital. 1961, 91, 849, 933;
12. R. Fusco, G. Bianchetti, D. Pocar, R. Ugo, Chem. Ber. 1963, 96, 802;
13. G. Bianchetti, D. Pocar, P. Dalla Croce, A. Vigevani, Chem. Ber. 1965, 98, 2715.
14. G. Bianchetti, P. Dalla Croce, D. Pocar, Tetrahedron Lett. 1965, 2039.
15. G. Bianchetti, D. Pocar, P. Dalla Croce, G. G. Gallo, A. Vigevani, Tetrahedron Lett. 1966, 1637;
16. G. Bianchetti, P. Dalla Croce, D. Pocar, R. Stradi, G. G. Gallo, Gazz. Chim. Ital. 1967, 97, 564.
17. M. Regitz, G. Himbert, Liebigs Ann. Chem. 1970, 734, 70.
18. Y. Sato, H. Kojima, H. Shirai, J. Org. Chem. 1976, 41, 195;
19. Y. Sato, H. Kojima, H. Shirai, J. Org. Chem. 1976, 41, 3325.
20. H. Quast, S. Ivanova, E.-M. Peters, K. Peters, Eur. J. Org. Chem. 2000, 507.
21. G. Maas, T. Mayer, Synthesis 1991, 1209.
22. W.-Q. Fan, A. R. Katritsky, in 'Comprehensive Heterocyclic Chemistry IF, Eds. A. R. Katritsky, C. W. Rees, and E. F. V. Scriven, Vol. 4, Ed. R. S. Storr, Pergamon/Elsevier, Oxford, 1996, p. 1.
23. B. A. Trofimov, A. N. Vavilova, Russ. J. Org. Chem. 1986, 22, 420.
24. M. Brunner, R. Reinhard, R. Rahm, G. Maas, Synlett 1994, 627.
25. W. J. Le Noble, H, Kelm, Angew. Chem., Int. Ed. 1980, 19, 841;
26. W. J. Le Noble, 'Organic High Pressure Chemistry', Elsevier, Amsterdam, 1988.
27. F.-G. Klärner, F. Wurche, J. Prakt. Chem. 2000, 342, 609.
28. F. Wurche, F-G. Klärner, 'The Effect of Pressure on Organic Reactions: Basic Principles and Mechanistic Applications', in 'High-Pressure Chemistry', Eds. R. van Eldik, and F.-G. Klärner, Wiley-VCH, Weinheim, 2002, p. 41.
29. W. G. Dauben, R. A. Bunce, J. Org. Chem. 1982, 47, 5042;
30. G. T. Anderson, J. R. Henry, S. R. Weinreb, J. Org. Chem. 1991, 56, 6946.
31. J. W. Wijnen, R. A. Steiner, J. B. F. N. Engberts, Tetrahedron Lett. 1995, 36, 5389.
32. R. Huisgen, 'The Adventure Playground of Mechanisms and Novel Reactions', American Chemical Society, Washington, D.C., 1994, p. 90.
33. V. V. Rostovtsev, G. L. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem., Int. Ed. 2002, 41, 2596.
34. G. Grundmann, in 'Methoden der Organischen Chemie (Houben-Weyl)', Georg Thieme Verlag, Stuttgart, 1965, Vol. 10/3, p. 807.
35. W. Lwowski, T. W. Mattingly Jr., J. Am. Chem. Soc. 1985, 87, 1947.
36. M. Regitz, J. Hocker, A. Liedhegener, Org. Synth. 1968, 48, 38.
37. L. Brandsma, 'Preparative Acetylene Chemistry', 2nd edn., Elsevier, Amsterdam, 1988.