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Reduction and Reductive Alkylation of 3H-Isobenzofuran-1-ones

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The survey reports the reductive conversion of phthalides into ortho -alkylated carboxylic acids. This procedure is the most convenient and effective methodology for regiospecific syntheses of ortho-alkylated carboxylic acids. The literature up to the end of 2002 is reviewed.
Rocznik
Strony
1385--1410
Opis fizyczny
Bibliogr. 139 poz., rys.
Twórcy
autor
  • Department of Organic Chemistry, Institute of Chemistry, University of Łódź, 90-136 Łódź, Narutowicza 68, Poland
autor
  • Department of Organic Chemistry, Institute of Chemistry, University of Łódź, 90-136 Łódź, Narutowicza 68, Poland
  • Department of Organic Chemistry, Institute of Chemistry, University of Łódź, 90-136 Łódź, Narutowicza 68, Poland
Bibliografia
  • 1. Elderfield R.C., in “Heterocyclic compounds”, (Elderfield R.C., ed.), Vol. 2, p. 68. NY, 1951.
  • 2. Rodrigo R., Tetrahedron Lett., 44, 2093 (1988).
  • 3. Friedrichsen W,,Adv. Heterocycl. Chem., 26, 135 (1980).
  • 4. The Merck Index, 11th ed., Rahway 1989.
  • 5. Kende A.S. and Boettgcr S.D., J. Org. Chem., 46, 2799 (1981).
  • 6 Krapcho A.P., Getahun Z. and Avery K.J., Jr., Synth. Commun., 20, 2139 (1990).
  • 7. Patil M.L., Borate H.B., Ponde D.E., Bhawal B.M. and Deshpande V.H., Tetrahedron Lett., 40, 4437 (1999).
  • 8. Wulff W.D. and Tang P.-C., J. Am Chem. Soc., 106, 434 (1984).
  • 9. Iwao M., Mahalanabis K.K., Watanabe M., de Silva S.O. and Snieckus V., Tetrahedron, 39,1955 (1983).
  • 10. Dunsdon S.J. and Martin J.A., Tetrahedron, 41, 2919 (1985).
  • 11 Zani C.L., de Oliveira A.B. and Snieckus V., Tetrahedron Lett., 28, 6561 (1987).
  • 12- Starling S.M., Raslan D.S., de Oliveira A.B. and Zani C.L., Synth. Commun., 28, 3567 (1998).
  • 13.Lopes C.C., Lima L.S., Monteiro A.J. and CostaP.R.RSynth. Commun., 18, 1731 (1988).
  • 14.lio H., Zenfuku K. and Tokoroyama T., Tetrahedron Lett., 36, 5921 (1995).
  • 15. Falk H. and Mayr E., Monatsh. Chem., 126, 699 (1995).
  • 16. English D.S., Zhang W„ Kraus G.A. and Petrich J.W., J. Am. Chem. Soc., 119, 2980 (1997).
  • 17. Falk H. and Schoppel G., Monatsh. Chem., 122, 739 (1991).
  • 18. Falk H. and Mayr E., Monatsh. Chem., 126, 1311 (1995).
  • 19..Clar E. and Stewart D.G., J. Chem. Soc., 3215 (1951).
  • 20. Isola M. and Marsili A„ Tetrahedron, 23, 1037 (1967).
  • 21. Marsili A., J. Org. Chem., 32, 240 (1967).
  • 22. Bergmann E.D., Weiler-Feilchenweld H., Heller A., Britzman C. and Hirschfeld A., Tetrahedron Suppl. 7, 349(1966).
  • 23. Fouché J., Blondel J.-C., Horclois R., James C., Léger A. and Poiget G., Bull. Soc. Chim. Fr., 8, 3 (1972).
  • 24. Suzuki K., Weisburger E.K. and Weisburger J.H., J. Org. Chem., 26, 2236 (1961).
  • 25. Newman M.S. and Hussain N.S., J. Org. Chem., 47, 2837 (1982).
  • 26. Newman M.S., Prahbu V.S. and Veeraraghavan S., J. Org. Chem., 48, 2926 (1983).
  • 27. Newman M.S. and Veeraraghavan S., J. Org. Chem., 48, 3246 (1983).
  • 28. Sabhita G. and Yadav J.S., Synth. Commun., 28, 3065 (1998).
  • 29. Hudlickÿ M., “Reductions in Organic Chemistry”, Ellis Horwood, Chichester, 1986.
  • 30. Bartoszewicz R., Miecznikowska-Stolarczyk W. and Oprz^dek B., “Methods of Reduction of Orga Compounds”. Warszawa, 1956, (in Polish).
  • 31. de Silva S.O., Watanabe M. and Snieckus V., J. Org. Chem., 44, 4802 (1979).
  • 32. Manceron L. and Andrews L., J. Am. Chem. Soc., 110, 3840 (1988).
  • 33. Sammes P.G., Arnold B.J. and Mellows S.M., J. Chem. Soc., Perkin Trans. 1, 1266 (1973).
  • 34. Snieckus V. and Osmund S., Tetrahedron Lett., 51, 5103 (1978).
  • 35. Kelly T.R. and Parckh N.D., J. Org. Chem., 47, 5009 (1982).
  • 36. Falk H. and MayrE„Monatsh. Chem., 126, 1311 (1995).
  • 37. Nichols D.E., Snyder S.E., Aviles-Garay F.A., Chakraborti R., Watts V.J. and Mailman R.B., J. A Chem., 38, 2395(1995).
  • 38. Witiak D.T., Abdood N.A., Goswami S. and Milo G.E., J. Org. Chem., 51,4499 (1986).
  • 39. Castle N., Pratap R. and Tominaga Y., J. Heterocycl. Chem., 19, 865 (1982).
  • 40. Johnson F., Kimball S.D. and Walt D.R., J. Am. Chem. Soc., 103, 1561 (1981).
  • 41. Krapcho A.P., Getahun Z. and Avery K.J. Jr., Synth. Commun., 20, 2139 (1990).
  • 42. Iio H., Zenfuku K. and Tokoroyama T., Tetrahedron Lett., 36, 5921 (1995).
  • 43. Harvey R.G. and Cortez C., Tetrahedron, 53, 7101 (1997).
  • 44. Harvey G. and Cho B.P., J. Org. Chem., 52, 5668 (1987).
  • 45. Kraus G.A., English D.S. and Petrich J.W., J. Am. Chem. Soc., 119, 2980 (1997).
  • 46. Schultz A.G., McMahon W.G. and Kullnig R.K., J. Org. Chem., 52, 3905 (1987).
  • 47. Falk H. and Schoppel G., Monatsh. Chem., 122, 739 (1991).
  • 48. Proksa B., Uhrinovâ S., Adamcovâ J. and Fuska J., Monatsh. Chem., 123, 251 (1992).
  • 49. Newman M.S. and Wiseman E.H.,7. Org. Chem., 26, 3208(1961).
  • 50. Newman M.S. and Kannan R., J. Org. Chem., 44, 3388 (1979).
  • 51. Misra R.N., Brown B.R., Sher P.M., Patel M.M., Hall S.E., Han W.-C., Banish J.C., Kocy O., Ha D. N., Goldenberg H.J., Michel I.M., Schumacher W.A., Webb M.L., Moshizadegan H. and Oglel M.L,,J. Med. Chem., 36, 1401 (1993).
  • 52. Newman M.S. and Galt R.H.B., J Org. Chem., 25, 214 (1960).
  • 53. Birkinshaw J.H. and Gourlay R., J. Chem. Soc., 716 (1963).
  • 54. Yang C.-X. and Harvey R.G., Tetrahedron, 48, 3735 (1992).
  • 55. Harvey R.G., Aboshkara E. and Pataki J., Tetrahedron, 53, 15947 (1997).
  • 56. Uemura M., Minami T. and Hayashi Y., J. Chem. Soc., Chem. Commun., 17, 1193 (1984).
  • 57. Katsuura K. and Snieckus V., Can. J. Chem., 65, 124 (1987).
  • 58. Newman M.S., Cecil J.H. and Hung W.M., J. Med. Chem., 15, 569 (1972).
  • 59. Rama Rao A.V., Reddy K.B. and Mehendale A.R., J. Chem. Soc., Chem. Commun., 10, 564 (1983
  • 60. Newman M.S. and Tuncay A., J. Org. Chem., 45, 348 (1980).
  • 61. Newman M.S., Sankaran V. and Olson D.R., J. Am. Chem. Soc., 98, 3237 (1976).
  • 62. Sheikh Y.M., Ekwuribe N., Dhawan B. and Witiak D.T., J. Org. Chem., 47, 4341 (1982).
  • 63. Newman M.S. and Kumar A., J. Org. Chem., 51, 2379 (1986).
  • 64. Mills R.J. and Snieckus \.,J. Org. Chem., 54, 4386 (1989).
  • 65. Newman M.S., J. Org. Chem., 48, 3249 (1983).
  • 66. Harvey R.G. and Cortez C., Tetrahedron, 53, 7101 (1997).
  • 67. Kende A.S. and Boettger S.D., J. Org. Chem., 46, 2799 (1981).
  • 68. Wulff WD. and Tang P.-C., J. Am. Chem. Soc., 106, 434 (1984).
  • 69. Witiak D.T., Goswami S. and Milo G.E., J. Org. Chem., 53, 345 (1988).
  • 70. Patil M.L., Borate H.B., Ponde D.E., Bhawal B.M. and Deshpande V.H., Tetrahedron Lett., 40, 4437 (1999).
  • 71. Bentov M. and Bergmann E.D., Bull. Soc. Chim. Fr., 1316 (1961).
  • 72. Pataki J., Duguid C., Rabideau P.W., Huisman H. and Harvey R.G., J. Med. Chem., 14, 940 (1971).
  • 73. Bentov M. and Bergmann E.D., Bull. Soc. Chim. Fr., 963 (1963).
  • 74. Iwao M., Mahalanabis K.K., WatanabeM.,deSilvaS.O. and Snieckus V., Tetrahedron, 39,1955 (1983).
  • 75. Newman M.S. and Blum S.,J. Org. Chem., 29, 1414 (1964).
  • 76. Newman M.S. and Naiki K., J. Org. Chem., 27, 863 (1962).
  • 77. Letsinger R.L., Jamison J.D. and Hussey A.S., J. Org. Chem., 26, 97 (1961).
  • 78. Newman M.S. and Seshardi S., J. Org. Chem., 27, 76 (1962).
  • 79. Dunsdon S.J. and Martin J.A., Tetrahedron, 41, 2919 (1985).
  • 80. Bistrzycki A. and Krauer J., Helv. Chim. Acta, 6, 763 (1923).
  • 81. Bemer E., Acta Chem. Scand., 10, 1208 (1956).
  • 82. Ryer A.I. and Gebert W.H., J. Am. Chem. Soc., 74, 41 (1952).
  • 83. Schubert W.M., Rabinovitch B.S., Larson N.R. and Sims V.A., J. Am. Chem. Soc., 74, 4590 (1952).
  • 84. Koseki Y. and Nagasaka T., Chem. Pharm. Bull., 43, 1604 (1995).
  • 85. Topp A., Boldt P. and Schmand H., Liebigs Ann. Chem., 1167(1974).
  • 86. Bergmann E.D. and Blum J., J. Org. Chem., 27, 527 (1962).
  • 87. Brubaker M.M. and Adams R., J. Am. Chem. Soc., 49, 2279 (1927).
  • 88. Moldawski B.L. and Turetzkaya L.E., Zh. Ob. Khim., 16, 445 (1946).
  • 89. Bartlett P.D. and Jones J.E., J. Am. Chem. Soc., 64, 1837 (1942).
  • 90. Larsen R.D., Corley E.G., King A.O., Carroll J.D., Davis P., Verhoeven T.R. and Reider P.J., J. Org. Chem., 61, 3398 (1996).
  • 91. Kursanov D.N., Pames Z.N. and Loim N.M., Synthesis, 633 (1974).
  • 92. Joshi R.R. and Narasimhan N.S., Synthesis, 943 (1987).
  • 93. Gore V.G. and Narasimhan N.S., J. Chem. Soc., Perkin Trans. 1,481 (1988).
  • 94. Newman M.S. and Kanakarajan K., J. Org. Chem., 45, 2301 (1980).
  • 95. Kimbal S.D., Kim K.S., MohanthD.K., Vanotti E. and Johnson F., Tetrahedron Lett., 23,3871 (1982).
  • 96. Tauton J., Wood J.L. and Schreiber S.L., J. Am. Chem.Soc., 115, 10378(1993).
  • 97. Chikashita H., Porco J.A., Stout T.J., Clardy J. and Schreiber S.L., J. Org. Chem., 56, 1692 (1991).
  • 98. Epsztajn J., Bieniek A. and Kowalska J.A., Monatsh. Chem., 127, 701 (1996).
  • 99. Meegalla S.K. and Rodrigo R., Synthesis, 12, 924 (1989).
  • 100. Verdauguer X., Berk S.C. and Buchwald S.L., J. Am. Chem. Soc., 117, 12641 (1995).
  • 101.Horikawa Y., Watanabe M., Fujiwara T. and Takeda T., J. Am. Chem. Soc., 119, 1127(1997).
  • 102. Reetz M.T, Wolz P., Hübner F., Hüttenheim S.H., Heimbach H. and Schwellnus K., Chem. Ber., 117,322 (1984).
  • 103. Hunt J.T., Malley M.F. and Gougoutas J.Z., Heterocycles, 31, 1359 (1990).
  • 104. Homma K., Takenoshita H. and Mukaiyama T., Bull. Chem. Soc. Jpn., 63, 1898 (1990).
  • !05.Mukaiyama T., Homma K. and Takenoshita H., Chem. Lett., 10, 1725 (1988).
  • 106. Homma K. and Mukaiyama T., Chem. Lett., 1989, 893.
  • 107. Brownbridge P., Chan T.H., Brook M.A. and Kang G.J., Can. J. Chem., 61, 688 (1983).
  • 108. Chan T.-H. and Brownbridge P., J. Chem. Soc. Chem. Commun., 1, 20 (1981).
  • 109. van Oeveren A. and Feringa B.L., J. Org. Chem., 61, 2920 (1996).
  • 110. Kita Y.,SegawaJ.,HarutaJ.,YasudaH.andTamamuraY.,/ Chem. Soc. Perkin Trans. 1,1099(1982).
  • 111. Kiyooka S.-I. and Shirouschi M., J. Org. Chem., 57,1 (1992).
  • 112.MukayiamaT., Narasaka K. and Banno K., J. Am. Chem. Soc., 96, 7503 (1974).
  • 113. Mukayiama T.,/iHgew. Chem., Int. Ed. Engl., 16, 817 (1977).
  • 114. Grieco P.A. and Handy S.T., Tetrahedron Lett., 38, 2645 (1997).
  • 115. Epsztajn J., Bieniek A., Kowalska J.A. and Kulikiewicz K.K., Synthesis, 11, 1603 (2000).
  • 116. Node M., Nishide K., Ochiai M., Fuji K. and Fujita E., J. Org. Chem., 46, 5163 (1981).
  • 117. Streitweiser A., Jr., Ziegler G.R., Mowery P.C., Lewis A. and Lawler R.G., J. Am. Chem. Soc., 90, 1357 (1968).
  • 118. Burfeindt J., Patz M., Müller M. and Mayr H., J. Am. Chem. Soc., 120, 3629 (1998).
  • 119. Bieniek A., Epsztajn J. and Kulikiewicz K.K., Synth. Commun., 4, 667 (2003).
  • 120. Casiraghi G., Zauardi F., Appendino G. and Roussou G., Chem. Rev., 100, 1929 (2000).
  • 121. Bieniek A., Epsztajn J. and Kulikiewicz K.K., Monatsh. Chem., in press.
  • 122. Mukaiyama T. and Ischida A., Chem. Lett., 319 (1975).
  • 123. Mukaiyama T. and Ischida A., Chem. Lett., 1201 (1975).
  • 124. Mukaiyama T. and Ischida A., Chem. Lett., 467 (1977).
  • 125. Fleming I. and Lee T.V., Tetrahedron Lett., 22, 705 (1981).
  • 126. Chow H.F. and Fleming I., J. Chem. Soc. Perkin Trans 1, 2651 (1998).
  • 127. Angle S.R. and Louie M.S., Tetrahedron Lett., 30, 5741 (1989).
  • 128. Angle S.R. and Louie M.S., J. Org. Chem., 56, 2853, (1991) and references therein.
  • 129. Kaneko C., Sato M., Sakaki J. and Abe Y., J. Heterocyclic Chem., 27, 25 (1990).
  • 130. Clemens R.J. and Witzeman J.S., J. Am. Chem. Soc., Ill, 2186 (1989).
  • 131. Singer A.R. and Carreira M.E., J. Am. Chem. Soc., 117, 12360 (1995).
  • 132. Sato M., Sunami S., Sugita Y. and Kaneko C., Chem. Pharm. Bull., 42, 839 (1994).
  • 133. Bieniek A., Epsztajn J. and Kulikiewicz K.K., in preparation for press.
  • 134. Hall S.E., Med. Res. Rev., 11, 503 (1991).
  • 135. Ohkawa S., Terao T., Terashita Z., Shibouta Y. and Nishikawa K., J. Med. Chem., 34, 267 (1991).
  • 136. Ohkawa S., Terao S., Murakami M., Matsumoto T. and Goto G., Chem. Pharm. Bull., 39, 917 (1991
  • 137. Bhagwat S.S., Gude C., Cohen D.S., Lee W., Furness P. and Clarke F.H.,J.. Med. Chem., 34,1790 (1991
  • 138. Soyka R., Heckei A., Nicki J., Eisert W., Müller T.H. and Weisenberger H., J. Med. Chem., 37,26 (1994
  • 139. Miki I., Kishibayashi N., Takeda M., Suzuki K., Obase H. and Ishiii A., Arzneim.-Forsch., 45, 10i (1995).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0022-0006
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