Preparation of 2-alkylselenobenzothiazoles by the reaction of alcohols with 2-(2-oxoethylseleno)benzothiazoles in the presence of tertiary phosphines

Heterocycles

Volumn 50, Issue 2, 1999, Pages 947-966

  Shibata, Koichi ^a,b   Yamaga, Hiko ^a   Mitsunobu, Oyo ^a  

^a AOYAMA GAKUIN UNIVERSITY   (Japan)

^b CHISSO CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTANEDIOL; BENZOTHIAZOLE DERIVATIVE; HYDROXYL GROUP; METHANOL; PHOSPHINE DERIVATIVE;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; OXYGEN AFFINITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 0033117428     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-98-s(h)94     Document Type: Article

References (35)

1. For reviews of organoselenium compounds, see for example; a) D. L. J. Clive, Tetrahedron. 1978, 34, 1049.
2. b) C. Paulmier, "Selenium Reagents and Intermediates in Organic Synthesis," Pergamon Press, Oxford, 1986.
3. S. Patai and Z. Rappoport, ed., "The Chemistry of Organic Selenium and Tellurium Compounds (Vol. 1)," John Wiley & Sons, Chichester, 1986.
4. K. Shibata and O. Mitsunobu, Bull. Chem. Soc. Jpn., 1992, 65, 3163.
5. Some of this work appeared as a preliminary communication; K. Shibata and O. Mitsunobu, Chem. Lett., 1993, 549.
6. 2P-OR′ (R′ = alkyl group) react with α-halo ketones and α-halo esters to give either enol phosphates (Perkow reaction) or ketophosphonates (Arbuzov reaction) depending on the structures of reactants. When phosphine is used in the place of phosphite, enol phosphonium salt is generated. (formula presented)
7. a) J. I. G. Cadogan ed., "Organophosphorus Reagents in Organic Synthesis," Academic Press, New York, 1979.
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11. In the reaction of a-halo ketones with P(III)-compounds, the phosphorous compound initially attacks the halogen atom. See for example, a) I. J. Borowitz and L. I. Grossman, Tetrahedron Lett, 1962, 471.
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13. 3P gave alkyl aryl selenides, where selenophosphonium salts are proposed as a key intermediate. P. A. Grieco, S. Gilman, and M. Nishizawa, J. Org. Chem., 1976, 41, 1485. See also, M. Sevrin and A. Krief, J. Chem. Soc., Chem. Commun., 1980, 656; P. A. Grieco, J. Y. Jaw, D. A. Claremon, and K. C. Nicolaou, J. Org. Chem., 1981, 46, 1215.
14. 3P gave alkyl aryl selenides, where selenophosphonium salts are proposed as a key intermediate. P. A. Grieco, S. Gilman, and M. Nishizawa, J. Org. Chem., 1976, 41, 1485. See also, M. Sevrin and A. Krief, J. Chem. Soc., Chem. Commun., 1980, 656; P. A. Grieco, J. Y. Jaw, D. A. Claremon, and K. C. Nicolaou, J. Org. Chem., 1981, 46, 1215.
15. 3P gave alkyl aryl selenides, where selenophosphonium salts are proposed as a key intermediate. P. A. Grieco, S. Gilman, and M. Nishizawa, J. Org. Chem., 1976, 41, 1485. See also, M. Sevrin and A. Krief, J. Chem. Soc., Chem. Commun., 1980, 656; P. A. Grieco, J. Y. Jaw, D. A. Claremon, and K. C. Nicolaou, J. Org. Chem., 1981, 46, 1215.
16. b) Arylselenophosphonium salts are also formed in the reaction of diaryl diselenides with phosphines. See for example, M. Sakakibara, K. Katsumata, Y. Watanabe, T. Toru, and Y. Ueno, Synthesis, 1992, 377, and refs therein.
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20. The reaction of 11 with 19c and 3b (molar ratio = 1:1:1.2) in THF at rt for 17.4 h gave 12c and 20 in 65% and 1 % yields, respectively with 31% recovery of 11. For the related reaction, see T. Nakagawa and T. Hata, Tetrahedron Lett., 1975, 1409. See also; T. Hata and M. Sekine, Tetrahedron Lett., 1974, 3943. T. Hata and M. Sekine, Chem. Lett., 1974, 837. T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 1976, 15, 94. Ref. 7b.
21. The reaction of 11 with 19c and 3b (molar ratio = 1:1:1.2) in THF at rt for 17.4 h gave 12c and 20 in 65% and 1 % yields, respectively with 31% recovery of 11. For the related reaction, see T. Nakagawa and T. Hata, Tetrahedron Lett., 1975, 1409. See also; T. Hata and M. Sekine, Tetrahedron Lett., 1974, 3943. T. Hata and M. Sekine, Chem. Lett., 1974, 837. T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 1976, 15, 94. Ref. 7b.
22. The reaction of 11 with 19c and 3b (molar ratio = 1:1:1.2) in THF at rt for 17.4 h gave 12c and 20 in 65% and 1 % yields, respectively with 31% recovery of 11. For the related reaction, see T. Nakagawa and T. Hata, Tetrahedron Lett., 1975, 1409. See also; T. Hata and M. Sekine, Tetrahedron Lett., 1974, 3943. T. Hata and M. Sekine, Chem. Lett., 1974, 837. T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 1976, 15, 94. Ref. 7b.
23. The reaction of 11 with 19c and 3b (molar ratio = 1:1:1.2) in THF at rt for 17.4 h gave 12c and 20 in 65% and 1 % yields, respectively with 31% recovery of 11. For the related reaction, see T. Nakagawa and T. Hata, Tetrahedron Lett., 1975, 1409. See also; T. Hata and M. Sekine, Tetrahedron Lett., 1974, 3943. T. Hata and M. Sekine, Chem. Lett., 1974, 837. T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 1976, 15, 94. Ref. 7b.
24. a) O. Mitsunobu, "Rin-Tsukaikata no Kotsu," in "Yuki Gosei no Shin Han'nozai," ed., by H. Nozaki, T. Mukaiyama, and H. Yamamoto, Kagaku Dojin, Kyoto, 1982, pp. 123-132.
25. b) R. Appel and M. Halstenberg, "Functional Group Conversion using Phosphorus (III) Reagents and Polyhalogenoalkanes," in "Organophosphorus Reagents in Organic Synthesis," ed. by J. I. G. Cadogan, Academic Press, London, 1979, pp. 387-431.
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28. In order to dissolve 0.069 g (0.5 mmol) of 1-phenyl-1,2-ethanediol (28a), 7 mL of benzene was required, while 1.5 mL of THF was sufficient to complete solution.
29. 12
30. K. Takemura, K. Sakano, A. Takahashi, T. Sakamaki, and O. Mitsunobu, Heterocycles, 1989, 47, 633.
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32. Beilstein Handbuch der Organischen Chemie, Berlin, 1925, Vol. 7, 436.
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34. P. Nicpon and D. W. Meek, "Inorg. Synth.," ed, by E. L. Muetterties, McGraw-Hill, New York, 1967, Vol. 10, p. 157.
35. 2 in 62% yield: J. W. Warner, J. Org. Chem., 1963, 28, 1642.