Mercury(II) chloride-mediated cyclization - Rearrangement of O-propargylglycolaldehyde dithioacetals to 3-pyranone dithioketals: An expeditious access to 3-pyranones

Organic Letters

Volumn 7, Issue 2, 2005, Pages 207-210

  Ghorai, Subir ^a   Bhattacharjya, Anup ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALDEHYDE; ALDEHYDE DERIVATIVE; GLYCOL; KETONE DERIVATIVE; MERCURY CHLORIDE; PYRAN DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS;

EID: 13444261087     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047893a     Document Type: Article

References (26)

1. (a) Larock, R. C. Solvomercuration/Demercuration Reactions in Organic Synthesis; Springer-Verlag: Berlin, 1986.
2. (b) Larock, R. C. Tetrahedron 1982, 38, 1713-1754.
3. (a) Larock, R. C.; Harrison, L. W. J. Am. Chem. Soc. 1984, 106, 4218-4227.
4. (b) Riediker, M.; Schwartz, J. J. Am. Chem. Soc. 1982, 104, 5842-5844.
5. (c) Nishizawa, M.; Takao, H.; Yadav, V. K.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 4563-4565.
6. (d) Bates, D. K.; Jones, M. C. J. Org. Chem. 1978, 43, 3775-3776.
7. (e) Thyagarajan, B. S.; Majumdar, K. C.; Bates, D. K. J. Heterocycl. Chem. 1975, 12, 59-66.
8. (f) Balasubhramanian, K. K.; Reddy, K. V.; Nagarajan, R. Tetrahedron Lett. 1973, 14, 5003-5004.
9. (g) Imagawa, H.; Kurisaki, T.; Nishizawa, M. Org. Lett. 2004, 6, 3679-3681.
10. (h) Nishizawa, M.; Yadav, V. K.; Skwarczynski, M.; Takao, H.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 1609-1611.
11. (i) Nishizawa, M.; Skwarczynski, M.; Imagawa, H.; Sugihara, T. Chem. Lett. 2002, 12-13.
12. (j) Frederickson, M.; Grigg, R. Org. Prep. Proc. Int. 1997, 29, 63-116.
13. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley & Sons: New York, 1999; pp 329-344.
14. (a) Krishna, U. M.; Deodhar, K. D.; Trivedi, G. K. Tetrahedron 2004, 60, 4829-4836 and references therein.
15. (b) Jung, M. E.; Pontillo, J. J. Org. Chem. 2002, 67, 6848-6851.
16. (c) Sugawara, K.; Imanishi, Y.; Hashiyama, T. Tetrahedron: Asymmetry 2000, 11, 4529-4535.
17. (d) van der Deen, H.; van Oeveren, A.; Kellogg, R. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 1755-1758 and references therein.
18. (e) Dauben, W. G.; Kowalczyk, B. A.; Lichtenthaler, F. W. J. Org. Chem. 1990, 55, 2391-2398 and references therein.
19. (f) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Boulton, A. J., McKillop, A., Eds.; Pergamon: Oxford, 1984; Vol. 3, pp 843-844.
20. Meyers, A. I.; Comins, D. L.; Roland, D. M.; Henning, R.; Shimizu, K. J. Am. Chem. Soc. 1979, 101, 7104-7105.
21. Mukhopadhyay, R.; Kundu, A. P.; Bhattacharjya, A. Tetrahedron Lett. 1995, 36, 7729-7730.
22. Fetizon, M.; Jurion, M. J. Chem. Soc., Chem. Commun. 1972, 382-383.
23. Page, P. C. B.; van Niel, M. B.; Proger, J. C. Tetrahedron 1989, 45, 7643-7677.
24. 1H NMR spectra. The IR and mass spectral data also agreed well with the structures.
25. Examples of preparing 6H-pyran-3-ones from aldehydes and ketones are scarce. In one example, a pyranone having the same skeleton as the ones reported in this work has been synthesized from a methyl ketone via a multistep sequence (ref 4b).
26. Capture of the electrophilic vinyl carbonium ion formed after complexation with Hg(II) by a neighboring sulfur (ref 2a) as well as oxygen atoms (refs 1, 2a, 2b, and 2g) is well precedented. In some of these instances, a substituent attached to the heteroatom is cleaved in the next step, affording sulfur and oxygen heterocycles.