A simple one-pot method for the preparation of allyl azides from allyl alcohols using triphosgene: Synthesis of N1-cinnamyl azetidin-2-ones

Synlett

Volumn , Issue 6, 2004, Pages 979-982

  Jayanthi, A ^a   Gumaste, V K ^a   Deshmukh, A R A S ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Allyl alcohols; Allyl azides; Azetidin 2 ones; Triphosgene

Indexed keywords

ALLYL ALCOHOL; AZETIDINE; AZIDE; PHOSGENE; SODIUM AZIDE;

ARTICLE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 3142698284     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-820046     Document Type: Article

References (31)

1. (a) Cotarca, L.; Delogu, P.; Nardelli, A.; Sunjic, V. Synthesis 1996, 553.
2. (b) Heintzelman, G. R.; Fang, W. K.; Keen, S. P.; Wallace, G. A.; Weinreb, S. M. J. Am. Chem. Soc. 2001, 123, 8851.
3. (c) White, J. D.; Hansen, J. D. J. Am. Chem. Soc. 2002, 124, 4950.
4. (a) Krishnaswamy, D.; Bhawal, B. M.; Deshmukh, A. R. A. S. Tetrahedron Lett. 2000, 41, 417.
5. (b) Krishnaswamy, D.; Govande, V. V.; Gumaste, V. K.; Bhawal, B. M.; Deshmukh, A. R. A. S. Tetrahedron 2002, 58, 2215.
6. Patil, R. T.; Ghazala, P.; Gumaste, V. K.; Bhawal, B. M.; Deshmukh, A. R. A. S. Synlett 2002, 1455.
7. Gumaste, V. K.; Bhawal, B. M.; Deshmukh, A. R. A. S. Tetrahedron Lett. 2002, 43, 1345.
8. (a) Patai, S. The Chemistry of Azido Group; Interscience: New York, 1971, 83-85.
9. (b) Molina, P.; Alajarin, M.; Lopez-Leonardo, C. Tetrahedron Lett. 1991, 32, 4041.
10. Cheikh, R. B.; Chaabouni, R.; Laurent, A.; Mison, P.; Nafti, A. Synthesis 1983, 685.
11. (a) Crandall, J. K.; Michaely, W. J. J. Org. Chem. 1984, 49, 4244.
12. (b) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem. 1990, 55, 3274.
13. (c) Sampath Kumar, H. M.; Subba Reddy, B. V.; Anjaneyulu, S.; Yadav, J. S. Tetrahedron Lett. 1998, 39, 7385.
14. (d) Malkov, A. V.; Spoor, P.; Vinader, V.; Kocovsky, P. J. Org. Chem. 1999, 64, 5308.
15. (e) Reddy, G. V. S.; Venkatrao, G.; Subramanyam, R. V. K.; Iyengar, D. S. Synth. Commun. 2000, 30, 2233.
16. (f) Chandrasekhar, S.; Raza, A.; Takhi, M. Tetrahedron: Asymmetry 2002, 13, 423.
17. (a) Murahashi, S. I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y. J. Org. Chem. 1989, 54, 3292.
18. (b) Murahashi, S. I.; Tanigawa, Y.; Imada, Y.; Taniguchi, Y. Tetrahedron Lett. 1986, 27, 227.
19. (c) Safi, M.; Fahrang, R.; Sinou, D. Tetrahedron Lett. 1990, 31, 527.
20. (a) Priebe, H. Acta Chem. Scand., Ser. B 1984, 38, 895.
21. (b) Kozaburo, N.; Hiroshi, K. Chem. Lett. 1982, 1477.
22. (a) Arimoto, M.; Yamaguchi, H.; Fujita, E.; Nagao, Y.; Ochiai, M. Chem. Pharm. Bull. 1989, 37, 3221.
23. (b) Arimoto, M.; Yamaguchi, H.; Fujita, E.; Ochiai, M.; Nagao, Y. Tetrahedron Lett. 1987, 28, 6289.
24. 3): δ = 4.88 (d, J = 6.0 Hz, 2 H), 6.25-6.35 (m, 1 H), 6.73 (d, J = 16.0 Hz, 1 H), 7.20-7.45 (m, 5 H).
25. Cinnamyl azide (1) and other allyl azides were found to be stable at r.t. but for safety reason they were stored in the refrigerator. [CAUTION: We did not observe any untoward incidence while working with allyl azides. However, the use of hood and safety shield is recommended, as azides are known for their explosive property].
26. +], 130 (57), 117 (100), 104 (74).
27. 3N, triphosgene and sodium azide with the loss of ethyl group. This reaction will be studied in detail and results will be communicated in future.
28. (a) Joshi, S. N.; Puranik, V. G.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron: Asymmetry 2001, 12, 3073.
29. (b) Joshi, S. N.; Phalgune, U. D.; Bhawal, B. M.; Deshmukh, A. R. A. S. Tetrahedron Lett. 2003, 44, 1827.
30. 2: C, 81.27; H, 6.27; N, 3.79. Found: C, 81.44; H, 6.33; N, 3.67.
31. Garegg, P. J.; Samuelsson, B. J. Chem. Soc., Perkin Trans, 1 1980, 2866.