Pyrolysis of perhydro[1,2-c][1,3]oxazines: A green method of synthesizing 2,3-dehydropiperidine enamines

Tetrahedron Letters

Volumn 46, Issue 33, 2005, Pages 5451-5454

  Cook, A Gilbert ^a   Schering, Christine A ^a   Campbell, Pauline A ^a   Hayes, Samantha S ^a  

^a VALPARAISO UNIVERSITY   (United States)

Author keywords

Azomethine ylides; Enamines; Microwave; Oxazines; Pyrolysis

Indexed keywords

ALDEHYDE; KETONE DERIVATIVE; OXAZINE DERIVATIVE; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HEAT TREATMENT; MICROWAVE IRRADIATION; PYROLYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 22144478720     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.067     Document Type: Article

References (22)

1. L.W. Haynes, and A.G. Cook A.G. Cook Enamines: Synthesis, Structure, and Reactions 2nd ed. 1988 Dekker New York Chapter 2
2. O. Cervinka Z. Rapport The Chemistry of Enamines, Part 1 1994 Wiley New York Chapter 9
3. N.J. Leonard, and F.P. Hauck Jr. J. Am. Chem. Soc. 79 1957 5279
4. N.J. Leonard, C.K. Steinhardt, and C. Lee J. Org. Chem. 27 1962 4027
5. R.V. Stevens, R.K. Mehra, and R.L. Zimmerman J. Chem. Soc., Chem. Commun. 1969 877
6. R. Lukes Collect. Czech. Chem. Commun. 2 1931 531
7. P. Beeken, and F.W. Fowler J. Org. Chem. 45 1980 1336
8. B.K. Warren, and E.E. Knaus J. Heterocycl. Chem. 24 1987 1413
9. C.H. Tilford, and M.G. Van Campen Jr. J. Am. Chem. Soc. 76 1954 2431
10. Flash vacuum thermolysis has been reviewed by: U.E. Wiersum Recl. Trav. Chim. Pays-Bas. 101 1982 317 The apparatus used consisted of a 530 × 25 mm quartz pyrolysis tube filled with 6 × 6 mm pieces of quartz packing, and a Lindbert/Blue M tube furnace with a maximum temperature of 1100°C. A 0.1 mm of Hg vacuum was used after flushing the apparatus with nitrogen. The product was trapped at -78°C
11. Milestone ETHOS SYNTH Labstation with magnetic stirring, ATC-FO Automatic Temperature Control, glass reaction vial with Teflon cover and screw cap. It was held at 160 C for 1 h and 200 C for 1 3/4 h using 500 W power.
12. M. Rink, and H.W. Eich Naturwissenschaften 45 1958 516
13. H. Oediger, and N. Joop Liebigs Ann. Chem. 764 1972 21
14. C. Najera, and J.M. Sansano Curr. Org. Chem. 7 2003 1105
15. R. Bureau, J. Mortier, and M. Joucla Bull. Soc. Chim. Fr. 130 1993 584
16. K. Hess, and W. Corleis Chem. Ber. 54B 1921 3010
17. L.H. Goodson, and H. Christopher J. Am. Chem. Soc. 72 1950 358
18. F.J. McCarty, C.H. Tilford, and M.G. Van Campen Jr. J. Am. Chem. Soc. 79 1957 472
19. S. Kasuga, and T. Taguchi Chem. Pharm. Bull. 13 1965 233
20. D. Ghiringhelli, and L. Bernardi Tetrahedron Lett. 1967 1039
21. H.C. Beyerman, L. Matt, A. Van Veen, and A. Zweistra Rec. Trav. Chim. 84 1965 1367
22. T.A. Crabb J.B. Lambert Y. Takeuchi Cyclic Organonitrogen Stereodynamics 1992 VCH New York Chapter 8