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Syntezy układu tiazolo[4,5-d]pirymidyny

Becan L.

Wiadomości Chemiczne

2014

[Z] 68, 1-2

95--116

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].