Preparation of 4-Alkoxy-1-hydroxypyridine-2-thiones

• Autorzy: Jankowiak A. , Jakowiecki J. , Kaszynski P.
• Języki publikacji: EN

Abstrakty

EN

Reations of 2-chloro-4-fluoropyridine (8), 2-chloro-4-nitropyridine (9), and their corresponding N-oxides 7 and 3 with the n-heptanolate anion were investigated in three solvents. The desired 2-chloro-4-heptyloxypyridine-N-ox ide (4a) was obtained most efficiently from 3 in DMSO. A reaction of 4a with AcSNa followed by deacetylation with MeONa gave the sodium salt of 4-heptyloxy-1-hydroxypyridine-2-thione (1a), which was iso - lated as the adamantane-1-carboxylate O-es ter 2a. Similarly, the 4-decyloxy and 4-((Z)- hex-3-enyloxy) derivatives 2b and 2c were prepared from 3.

Słowa kluczowe

EN

heterocycles; pyridine-2-thione; aromatic nucleophilic substitution

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2007
• Tom: Vol. 81, nr 11
• Strony: 1869--1877
• Opis fizyczny: Bibliogr. 23 poz., rys.

Twórcy

autor

Jankowiak A.

autor

Jakowiecki J.

autor

Kaszynski P.

• Organic Materials Research Group, Department of Chemistry, Vanderbilt University, Nashville, TN 37235, USA,

Bibliografia

• 1. Knight D.W., in: Encyclopedia of Reagents for Organic Synthesis, L.A. Paquette Ed.; Wiley&Sons, New York, 1995, Vol. 4, pp. 2775-2778; Crich D., in: Comprehensive Organic Synthesis, B.M. Trost, I. Fleming, S.V. Ley, Eds.; Pergamon, New York 1991, Vol. 7, pp. 717-734, and references therein.
• 2. For instance Zinc Pyrithione (Zinc Omadine®). For properties and uses see: http://en.wikipedia.org/wiki/Zinc_pyrithione.
• 3. Edrissi M. and Massoumi A., Microchem. J., 16, 353 (1971); Edrissi M., Jadbabaee M.J. and Dalziel J.A.W., ibid 526; Edrissi M., Massoumi A. and Dalziel J.A.W., ibid 538.
• 4. Xiong R.-G., Song B.-L., You X.-Z., Mak T.C.W. and Zhou Z.-Y, Polyhedron, 15, 991 (1996).
• 5. Sun J.-Y, Qiu X.-L., Meng W.-D. and Qing F.-L., Tetrahedron, 62, 8702 (2006).
• 6. Rees C.W., J. Chem. Soc, 3684 (1956).
• 7. Puszko A. and Talik Z., Polish J. Chem., 65, 377 (1991).
• 8. Yale H.L., Losee K., Martins J., Holsing M., Perry F.M. and Bernstein J., J. Am. Chem. Soc., 75, 1933 (1953).
• 9. Shaw E., Bernstein J., Losee K. and Lott W.A., J. Am. Chem. Soc., 72, 4362 (1950).
• 10.Abramovitch R.A. and Knaus E.E., Heterocycl. Chem., 12, 683 (1975).
• 11.Puszko K.,PolishJ. Chem., 68, 657 (1994).
• 12.For instance: Shaw E.N. and Bernstein J., US Pat. 2686786 (1954); Bernstein J. and Losee K. A., US Pat. 2713049 (1955); Cislak F.E., US Pat. 2786847 (1957); Bouillon C, Kalopissis G. and Lang G., Ger. Offen. DE 2165752 (1972); Elslager E.F. and Worth D.F., Ger. Offen. DE 2407937 (1974); Muntwyler R.E., Ger. Offen. DE 2714041 (1977).
• 13.4-Methoxy and 4-ethoxy derivatives were mentioned in patent literature but no details were provided: Nakanishi M., Saheki S. and Iimori K, JP 47040057 and JP 47040052 (1972).
• 14.Zhong P., Guo S. and Song C, Synth. Commun., 34, 247 (2004).
• 15.Miller J., Aromatic Nucleophilic Substitution; Elsevier: New York, 1968.
• 16.Alker D., Ollis W.D. and Shahriari-Zavareh H., J. Chem. Soc. Perkin. Trans. 1, 1623 (1990).
• 17.Talik Z. Roczniki Chem., 35, 475 (1961).
• 18. Talik Z., Roczniki Chem., 36, 1313 (1962).
• 19. ConnonS.J.andHegartyA.F.,Eur. J. Org. Chem., 3411 (2004)
• 20. Kim B. Y., Ann J.B., Lee H. W., Kang S.K., Lee J.H., Shin J.S., Ahn S.K., Hong C.I.and YoonS.S.,Eur. J. Med. Chem. Chim. Ther, 39, 433 (2004).
• 21. Kuduk S.D., DiPardo R.M. and Bock M.G., Org. Lett., 1, 577 (2005).
• 22. Walters M.A. and Shay J.J., Tetrahedron Lett, 36, 7575 (1995).
• 23. Coperet C, Adolfsson H., Khuong T.-A.V., Yudin A.K. and Sharpless K.B., J. Org. Chem., 63, 1740 (1998).