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Syntezy układu tiazolo[4,5-d]pirymidyny

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EN
Syntheses of the thiazolo[4,5-d]pyrimidine system
Języki publikacji
PL
Abstrakty
EN
This review is focused on the literature data about the preparation of the thiazolo[4,5-d]pyrimidine scaffold. The synthesis of this ring system has been accomplished by various methods. The synthesis can proceed via a pyrimidine onto which a thiazole ring can be annulated. The second approach involve annulation of a pyrimidine ring onto the preformed thiazole ring. Thiazolo[4,5-d]pyrimidines have been obtained by condensation of pyrimidine derivatives with thioamides [2], thionyl chloride [3], thiourea [4], bromomalononitrile [5], isothiocyanates [6] or under the influence of temperature [7]. However, most of the literature refers the methods of synthesis which begin with formation of the appropriately substituted thiazole ring. This synthetic route for preparation of fused derivatives utilizes orhtoesters [8, 9], acetic anhydride [9,10], formic acid derivatives [11, 12], carbon disulfide [13,14], appropriate isothiocyanates [15-18], urea and hydrazine derivatives [19–23], aromatic aldehydes and acid chlorides [24, 25] as key building blocks. Cyclization also occurs in high temperature or acidic reaction medium [26, 27]. The solid-phase synthesis was also described [28].
Rocznik
Strony
95--116
Opis fizyczny
Bibliogr. 28 poz., schem.
Twórcy
autor
  • Katedra i Zakład Technologii Leków Uniwersytet Medyczny im. Piastów Śląskich we Wrocławiu ul. Borowska 211a, 50-556 Wrocław
Bibliografia
  • [1] L. Becan, Wiad. Chem., 2013, 11–12, 1051.
  • [2] H. Erlenmeyer, H.P. Furger, Helv. Chim. Acta, 1943, 26, 366.
  • [3] M. Ichiba, K. Senga, J. Heterocycl. Chem., 1985, 22, 381.
  • [4] J.C. Sircar, M.J. Suto, M.E. Scott, M.K. Dong, R.B. Gilbersten, J. Med. Chem., 1986, 29, 1804.
  • [5] S.M. Sherif, M.M. Youssef, K.M. Mobarak, A.-S.M. Abdel-Fattah, Tetrahedron, 1993, 49, 9561.
  • [6] M. Bakavoli, M. Nikopour, M. Rahimizadeh, J. Heterocycl. Chem., 2006, 43, 1327.
  • [7] S. KarlstrOm, G. Nordval, D. Sohn, A. Hettman, D. Turek, K. Ahlin, A. Kers, M. Claesson et al., J. Med. Chem., 2013, 56, 3177.
  • [8] K. Gewald, Journal für praktische Chemie, 1966, 32, 26.
  • [9] H.T.Y. Fahmy, S.A.F. Rostom, M.N. Saudi, J.K. Zjawiony, D.J. Robins, Arch. Pharm. Pharm. Med. Chem., 2003, 336, 216.
  • [10] S.M. Rida, N.S. Habib, E.A.M. Badawey, H.T.Y. Fahmy, H.A. Ghozlan, Pharmazie, 1996, 51, 927.
  • [11] D. Wobig, Liebigs Ann. Chem., 1989, 4, 409.
  • [12] F. Azam, I.A. Alkskas, M.A. Ahmed, Eur. J. Med. Chem., 2009, 44, 3889.
  • [13] N.S. Habib, S.M. Rida, E.A.M. Badawey, H.T.Y. Fahmy, Monatschefte fur Chemie, 1996, 127, 1203.
  • [14] H.T.Y. Fahmy, S.A.F. Rostom, A.A. Bekhit, Arch. Pharm. Pharm. Med. Chem., 2002, 5, 213.
  • [15] E.A.M. Badaway, S.M. Rida, A.A. Hazza, H.T.Y. Fahmy, Y.M. Gohar, Eur. J. Med. Chem., 1993, 28, 91.
  • [16] H. Urgun, A. Balkan, M. Ozalp, Arzneim.-Forsch./Drug Res, 2000, 50, 1115.
  • [17] C. Hahnemann, H. Hartmann, Helv. Chim. Acta, 2003, 86, 1949.
  • [18] M. Gruner, M. Rehwald, K. Eckert, K. Gewald, Hetrocycles, 2000, 53, 2363.
  • [19] K. Gewald, U. Hain, R. Schindler, Monatschefte fur Chemie, 1994, 125, 1129.
  • [20] P.M. Luthra, C.B. Mishra, P.K. Jha, S.K. Barodia, Bioorg. Med. Chem. Lett., 2010, 20, 1214.
  • [21] M. Chhabria, I. Rathod, K. Vala, P. Patel, Med. Chem. Res., 2011, 20, 1450.
  • [22] V.V. Dabholkoar, S.S. Ahmed, Indian J. Chem., 2004, 43B, 2646.
  • [23] J.D. Akbari, K.B. Mehta, S.J. Pathak, H.S. Joshi, Indian J. Chem., 2008, 47B, 477.
  • [24] L. Becan, E. Wagner, Arzneim.-Forsch./Drug Res., 2008, 58, 521.
  • [25] H.A. H. El-Sherief, Z.A. Hozien, A.F.M. El-Mahdy, A.A. O. Sarhan, ARKIVOC, 2011, 10, 71.
  • [26] P. Molina, A. Arques, M.V. Vinader, J. Becher, K. Brondum, J. Org. Chem., 1988, 53, 4654.
  • [27] V.A. Artyomov, L.A. Rodinowskaya, A.M. Shestopalov, V.P. Litvinov, Tetrahedron, 1996, 52, 1011.
  • [28] T. Lee, J.H. Park, D.H. Lee, Y.D. Gong, J. Comb. Chem., 2009, 11, 495.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-45a16d5f-a96f-4e02-a450-de015aa88e8d
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