Approaches to Fused Pyrimidine Derivatives by the Pyrimidine Ring Construction and Their Application to Synthesis of Purines

• Autorzy: Ostrowski S.
• Języki publikacji: EN

Abstrakty

EN

Fused pyrimidines can be easily synthesized from the corresponding ortho-aminobenzylamine derivatives or their heteroanalogues. ortho-Nitrobenzaldehydes, ortho-aminobenzaldehydes, anthranilic acid derivatives, ortho-isocyanatobenzoates, ortho-aminobenzonitriles, ortho-isocyanatobenzonitriles, N-substituted anilines, ortho-halobenzoates, benzenediazonium salts, (2-nitroaryl)methylisocyanides, and derivatives of the all above compounds were also used for this purpose. Often the limiting factor for the above syntheses is the difficulty encountered in obtaining the key intermediates or their precursors. Recently, this problem was successfully solved in several ways by the use ofVicarious Nucleophilic Substitution of Hydrogen (VNS). As a result, many quinazolines and new bicyclic and tricyclic heteroaromatic compounds and their mono-N-oxides were obtained, when starting from aromatic nitro compounds. These approaches were also successfully applied to the synthesis of purines with the use of 4-nitroimidazole derivatives.

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2001
• Tom: Vol. 75, nr 11
• Strony: 1661--1687
• Opis fizyczny: Bibliogr. 131 poz., rys.

Twórcy

autor

Ostrowski S.

• Institute of Chemistry, University of Podlasie, ul. 3-Maja 54, PL-08-110 Siedlce, Poland fax: [phone],

Bibliografia

• 1. Armarego W.L.F., in The Chemistry of Heterocyclic Compounds, Fused Pyrimidines, Part I: “Quinazolines”, Brown D.J., ed.; vol. 24/1, Interscience Publishers: NY - London - Sydney, 1967.
• 2. Lister J.H., in The Chemistry of Heterocyclic Compounds, Fused Pyrimidines, Part II: “Purines”, Brown D. J., ed.; vol. 24/2, Wiley - Interscience: NY - London - Sydney - Toronto, 1971.
• 3. Brown D.J., in The Chemistry of Heterocyclic Compounds, Fused Pyrimidines, Part III: “Pteridines”, Taylor E.C., ed.; vol. 24/3, J. Wiley & Sons: NY - Chichester - Brisbane - Toronto - Singapore, 1988.
• 4. Delia T.J., in The Chemistry of Heterocyclic Compounds, Fused Pyrimidines, Part IV: “Miscellaneous Fused Pyrimidines”, Taylor E.C., ed.; vol. 24/4, J. Wiley & Sons, Inc.: NY - Chichester - Brisbane - Toronto - Singapore, 1992.
• 5. Brown D.J., in The Chemistry of Heterocyclic Compounds, The Pyrimidines, Taylor E.C., ed.; vol. 23, J. Wiley & Sons: NY - Chichester - Brisbane - Toronto - Singapore, 1994.
• 6. Brown D.J., in The Chemistry of Heterocyclic Compounds, Quinazolines, Supplement I, Taylor E.C., ed.; vol. 55, J. Wiley&Sons,Inc.:NY-Chichester- Brisbane -Toronto-Singapore-Weinheim, 1996.
• 7. Katritzky A.R. and Rees C.W., Comprehensive Heterocyclic Chemistry, vol. 1, part 1, Meth-Cohn O., ed.; Pergamon Press: Oxford, 1984, pp. 143-199.
• 8. Katritzky A.R., Rees C.W. and Scriven E.F.V., Comprehensive Heterocyclic Chemistry II, vol. 6, Boulton A.J., ed.; Pergamon Press: Oxford - NY - Tokyo, 1996, pp. 195-231.
• 9. Ostrowski S., Polish J. Chem., 68,2237 (1994).
• 10. Ostrowski S., Synlett, 253 (1995).
• 11. Ostrowski S., Heterocycles, 43, 389 (1996).
• 12. Ostrowski S., J. Chem. Res. (S), 14 (1998); (M), 0180-0187 (1998).
• 13. Ostrowski S., Molecules, 4, 287 (1999).
• 14. Ostrowski S., unpublished results.
• 15. Ostrowski S. and Wolniewicz A.M., Chem. Heterocycl. Compounds, 806 (2000).
• 16. Mąkosza M. and Winiarski J., Acc. Chem. Res., 20, 282 (1987).
• 17. Mąkosza M. and Wojciechowski K, Liebigs Ann./Recueil, 1805 (1997).
• 18. Ref. [3], pp. 358-360.
• 19. Albert A., in Selective Toxicity: The Physico-Chemical Basis of Therapy, 7Ih ed., Chapman N.B. and Hall J.E., eds.; London, 1985, p. 347.
• 20. Weinstock J., Wilson J.W., Wiebelhaus V.D., Maass A.R., Brennan F.T. and Sosnowski G., J. Med. Chem., 11, 573 (1968).
• 21. Ref. [1], pp. 490-518.
• 22. Bough R.G., Gurd M.R., Hall J.E. and Lessel B., Nature, 200, 656 (1963).
• 23. Mehta D.R., Naravane J.S. and Desai R.M., J. Org. Chem., 28, 445 (1963).
• 24. Baker B.R., Schaub R.E., McEvoy F.J. and Williams J.H., J. Org. Chem., 17, 132 (1952).
• 25. Constantine J.W. and Hess H.-J., Eur. J. Pharmacol., 74, 227 (1981).
• 26. Armarego W.L.F. and Smith J.I., J. Chem. Soc. (C), 234 (1966).
• 27. Madding G.D., J. Org. Chem., 37, 1853(1972).
• 28. Derieg M.E., Fryer R.I., Hillery S.S., Metlesics W. and Silverman G., J. Org. Chem., 36, 782 (1971).
• 29. Haider N., Heinisch G. and Moshuber J., Arch. Pharm. (Weinheim, Ger), 325, 119(1992).
• 30. Byford A., Goadby P., Hooper M., KamathH.V. andKulkami S.N., Indian J. Chem., 27B, 396 (1988).
• 31. Ref. [8], pp. 211-212.
• 32. Armarego W.L.F., J. Chem. Soc., 561 (1962).
• 33. LeMahieu R.A., Carson M., Nason W.C., Parrish D.R., Welton A.F., Baruth H.W. and Yaremko B., J. Med. Chem., 26, 420 (1983). 
• 34. Nixon W.J., Jr., Garland J.T. and Blanton C.D., Jr., Synthesis, 56 (1980).
• 35. Ref. [1], pp. 74-78.
• 36. Mayer J. and Wagner E., J. Org. Chem., 8, 239 (1943).
• 37. a) KorbonitsD. and Kolonits P.,J. Chem. Res. (S), 209 (1988); (M), 1652 (1988); b) ibid. (S), 328 (1989).
• 38. Korbonits D. and Kolonits P., Acta Chim. Hung., 127, 795 (1990); C.A., 115, 71523 (1991).
• 39. Nakanishi S. and Massett S.S., Org. Prep. Proced. Int., 12, 219 (1980).
• 40. Taylor E.C., McKillop A. and Vromen S., Tetrahedron, 23, 885 (1967).
• 41. Bonola G., Da Re P., Magistretti M.J., Massarani E. and Setnikar I., J. Med. Chem., 11, 1136 (1968).
• 42. Cantarelli G., Farmaco, Ed. Sci., 25, 770 (1970).
• 43. Field G.F., Zally W.J. and Stembach L.H., J. Org. Chem., 36, 777 (1971).
• 44. Manhas M.S. and Amin S.G., J. Heterocycl. Chem., 14, 161 (1977).
• 45. Ref. [6], pp. 44-49.
• 46. Yale H.L. and Kalkstein M., J. Med. Chem., 10, 334 (1967).
• 47. Hammen P.D. and Allen D.J.M., J. Heterocycl. Chem., 24, 1701 (1987).
• 48. Wolfe J.F.,RathmanT.L., Sleevi M.C., Campbell J. A. and Greenwood T.D.,./ Med. Chem., 33,161 (1990).
• 49. Cho N.S., Song K.Y. and Parkanyi C., J. Heterocycl. Chem., 26, 1807 (1989).
• 50. Combs D.W. and Rampulla M.S., J. Heterocycl. Chem., 26, 1885 (1989).
• 51. PeetN.P., SunderS. and Barbuch R.J., J. Heterocycl. Chem., 17, 1513 (1980).
• 52. Gordeev M.F., Hui H.C., Gordon E.M. and Patel D.V., Tetrahedron Lett., 38, 1729 (1997).
• 53. Shishoo C.J., Devani M.B., Ananthan S., Jain K.S., Bhadti V.S., Mohan S. and Patel L.J., Indian J. Chem., Sect. B, 28, 1039 (1989).
• 54. Urleb U., J. Heterocycl. Chem., 35, 693 (1998).
• 55. Beam Ch.F., Heindel N.D., Chun M. and Stefański A., J. Heterocycl. Chem., 13, 421 (1976).
• 56. Canonne P., Heterocycles, 36, 1305 (1993).
• 57. Bell S.C. and Childress S.J., J. Org. Chem., 27, 1691 (1962).
• 58. Goto T, Kishi Y., Takahashi S. and Hirata Y., Tetrahedron, 21, 2059 (1965).
• 59. Albert A., in Advances in Heterocyclic Chemistry, Katritzky A.R., ed.; 31, 2 (1982).
• 60. Baker B.R. and Almaula P.I., J. Org. Chem., 27,4672 (1962).
• 61. Kano S., Tanaka Y., Sugino S. and Hibino S., Synthesis, 1980, 695.
• 62. Tomioka Y., Ohkubo K. and Yamazaki M., Chem. Pharm. Bull., 33, 1360 (1985).
• 63. Hosmane R.S., Lim B.B., Summers M.F., Siriwardane U., HosmaneN.S. and Chu S.S.C., J. Org. Chem., 53, 5309 (1988).
• 64. Brown D.J. and Ienaga K, J. Chem. Soc., Perkin Trans. I, 1975, 2182.
• 65. Foster Ch.H. and Elam E.U., J. Org. Chem., 41, 2646 (1976).
• 66. Schofield K, J. Chem. Soc., 1952, 1927.
• 67. Bergman J., Brynolf A., Elman B. and Vuorinen E., Tetrahedron, 42, 3697 (1986).
• 68. Strekowski L., Cegła M.T., Harden D.B., Mokrosz J.L. and Mokrosz M.J., Tetrahedron Lett., 29,4265 (1988).
• 69. Desai K.R. and Desai P.H., J. Indian Chem. Soc., 65, 804 (1988).
• 70. Nielsen K.E. and Pedersen E.B., Chem. Scr., 18, 242 (1981).
• 71. Kokel B., Menichi G. and Hubert-Habart M., Tetrahedron Lett., 25, 1557 (1984).
• 72. Ref. [6], pp. 21-22.
• 73. Shiau C.-Y., Chem J.-W., Liu K.-C., Chan C.-H., Yen M.-H., Cheng M.-C. and Wang Y., J. Heterocycl. Chem., 27, 1467 (1990).
• 74. Pazdera P. and Pichler J., Chem. Pap., 45, 517 (1991).
• 75. Zinner G., Klein H. and KahnertH., Chem.-Ztg., Ill, 341 (1987); C.A., 109, 128939 (1988).
• 76. Taylor E.C. and McKillop A., The Chemistry of Cyclic Enamino-nitriles and ortho-Amino-nitriles, Wiley-Interscience: NY, 1970.
• 77. Taylor E.C., Patel H.H. and Jun J.-G., J. Org. Chem., 60, 6684 (1995).
• 78. Dean W.D. and Papadopoulos E.P., J. Heterocycl. Chem., 19, 171 (1982).
• 79. Uneyama K, Yamashita F., Sugimoto K. and Morimoto O., Tetrahedron Lett., 31, 2717 (1990).
• 80. Golomolzin B.V. and Postovskii I.Y., Khim. Geterotsikl. Soedin., 1970, 855.
• 81. Stankovsky S., Derer T. and Spirkova K, Monatsh. Chem., 124, 733 (1993). 
• 82. Rossi E., Celentano G., Stradi R. and Strada A., Tetrahedron Lett., 31, 903 (1990).
• 83. Rossi E., Calabrese D. and Farma F., Tetrahedron, 47, 5819 (1991).
• 84. Robev S.K., Tetrahedron Lett., 24, 4351 (1983).
• 85. Bandurco V.T., Schwender Ch.F., Bell S.C., Combs D.W., Kanojia R.M., Levine S.D., Mulvey D.M., Appollina M.A., Reed M.S., Malloy E.A., Falotico R., Moore J.B. and Tobia A.J., J. Med. Chem 30 1421 (1987).
• 86. Gewald K., Schafer H. and Mauersberger K., Z. Chim., 17, 223 (1977).
• 87. Goerdeler J. and Eggers W., Chem. Ber., 119, 3737 (1986).
• 88. Partridge M.W. and Smith A., J. Chem. Soc., Perkin Trans. 1, 1973,453.
• 89. Erian A.W. and Abu-Shanab F.A., Bull. Chem. Soc. Jpn., 71, 2387 (1998).
• 90. Huys F., Merényi R., Janousek Z., Stella L. and Viehe H.G., Angew. Chem., 91, 650 (1979).
• 91. Schmidt R.R., Schneider W., Karg J. and Burkert U., Chem. Ber., 105, 1634 (1972).
• 92. Olofson R.A. and Meer R.K.V., J. Org. Chem., 49, 3377 (1984).
• 93. Samokhvalov G.I., Med. Prom. SSSR, 11, 10 (1957); C.A., 52, 7334i (1958).
• 94. Glasby J.S., Encyclopaedia of Antibiotics, J. Wiley & Sons: Chichester - Brisbane - NY - Toronto, 1979.
• 95. Le Page G.A., Worth L.S. and Kimbal A.P., Cancer Res., 36, 1481 (1976).
• 96. McCarthy J.R., Stemerick D.M., Prakash N.J., Edwards M.L. and Jarvi E.T., Eur. Pat. Appl. EP 365,849 1990; C.A., 114, 24495p (1991).
• 97. Jeong L.S., Schinazi R.F., Beach J.W., Kim H.O., Nampalli S., Shanmuganathan K., Alves A.J., McMillan A., Chu C.K. and Mathis R., J. Med. Chem., 36, 181 (1993).
• 98. Barchi J. J., Jr., Marquez V.E., Driscoll J.S., Ford H., Jr., Mitsuja H., Shirasaka T., Aoki S. and Kelly J.A., J. Med. Chem., 34, 1647 (1991).
• 99. Prabhakar Y.S. andBhakuni D.S., Indian J. Biochem. Biophys., 27, 342 (1990); C.A., 114,156594e (1991).
• 100. Nord L.D., Dailey N.K., Me Keman P.A. and Robins R.K., J. Med. Chem., 30, 1044 (1987).
• 101. Effland R.Ch., Klein J.T., Davis L. and Olson G.E., Eur. Pat. Appl. EP 402,752, 1990- C A 114 P247683z (1991).
• 102. Kelly J.L., Krochmal M.P., Linn J.A., McLean E.W. and Soroko F.E., J. Med. Chem., 31, 606 (1988).
• 103. Merlos M., Gomez L., Vericat M.L., Bartroli J., Garcia-Rafanell J. and Fom J., Eur J Med. Chem 25 653 (1990).
• 104. Strong F.M., Skoog F. and Miller C.O., Ger. Pat. 1,026,334, 1958; C.A., 54, P18863h (1960).
• 105. Fischer K., Mayer H., Hamprecht G., Wuerzer B. and Westphalen K.O., Ger. Offen DE 3 921 271 1991; C.A., 114, P142981s (1991).
• 106. Ref. [2], pp. 31-90.
• 107. Lister J.H., in The Chemistry of Heterocyclic Compounds, The Purines; Supplement 1; Wiley-Interscience: NY - Chichester - Brisbane - Toronto - Singapore, 1996.
• 108. Bobrański B. and Synowiedzki Z., J. Am. Pharm. Assoc., Sci. Edu., 37, 62 (1948).
• 109. Kadir K, Shaw G. and Wright D., J. Chem. Soc., Perkin Trans. 1,1980, 2728.
• 110. Andersen K.E. and Pedersen E.B., Liebigs Ann. Chem., 1985, 921.
• 111. Birkett P.R., King H., Chapleo Ch.B., Ewing D.F. and Mackenzie D., Tetrahedron, 49, 11029 (1993).
• 112. Shaw G., J. Org. Chem., 30, 3371 (1965).
• 113. Yamazaki A., Kumashiro I. and Takenishi T., J. Org. Chem., 32, 3258 (1967).
• 114. Glushkov R.G. and Magidson O.Yu., Khim. Geterotsikl. Soedin., 85 (1965).
• 115. Baxter R.A. and Spring F.S., Nature, 154, 462 (1944).
• 116. Booth B.L. and Proenpa M.F., J. Chem. Soc., Chem. Commun., 788 (1981).
• 117. Albert A., J. Chem. Soc., Perkin Trans. 1, 2659(1973).
• 118. Prasad R.N. and Robins R.K., J. Am. Chem. Soc., 79, 6401 (1957).
• 119. Al-Shaar A.H.M., Gilmour D.W., Lythgoe D. J., McClenaghan I. and Ramsden Ch.A., J. Chem. Soc., Chem. Commun., 551 (1989).
• 120. Mąkosza M. and Owczarczyk Z., J. Org. Chem., 54, 5094 (1989).
• 121. Mąkosza M., Ostrowski S. and Kinowski A.J., Synthesis, 1215 (1993).
• 122. Katritzky A.R. and Lagowski J.M., in Chemistry of the Heterocyclic N-oxides, Blomquist A.T., ed.; Acad. Press: London - NY, 1971, pp. 19-141.
• 123. Adachi K., Yakugaku Zasshi, 77, 507, 514 (1957); C.A., 51, 14744Í, 14745Í (1957).
• 124. Stembach L.H., Kaiser S. and Reeder E., J. Am. Chem. Soc., 82, 475 (1960).
• 125. Stembach L.H., Reeder E., Keller O. and Matlesics W., J. Org. Chem., 26, 4488 (1961).
• 126. Schopf C., Hartmann A. and Koch K, Chem. Ber., 69, 2766 (1936).
• 127. Hansen S.B. and Petrow V., J. Chem. Soc., 350 (1953).
• 128. Taylor E.C., Cheng C.C. and Vogl O., J. Org. Chem., 24, 2019 (1959).
• 129. Cresswell R.M. and Brown G.-B., J. Org. Chem., 28, 2560 (1963).
• 130. Bodor N., Dewar M.J.S. and Harget A.J., J. Am. Chem. Soc., 92, 2929 (1970).
• 131. Al-Shaar A.H.M., Chambers R.K., Gilmour D.W., Lythgoe D.J., McClenaghan I. and Ramsden Ch.A., J. Chem. Soc., Perkin Trans. 1, 2779, 2789 (1992).