The review summarizes recent literatures dealing with the synthetic tools of thieno[2,3‐d]pyrimidine derivatives including their biological activities and their applications in the synthesis of heterocycles.
An efficient and ecofriendly method for the synthesis of disubstituted 5-aminopyrimidines from vinyl azides and urea or thiourea was developed. This reaction proceeds under microwave irradiation conditions in the presence of water as a solvent. The remarkable features of this new protocol are high conversion, short reaction times, cleaner reaction profiles and straightforward procedure.
in Wiley Online Library (wileyonlinelibrary.com).Diethyl azodicarboxylate and 3,4,5,6-tetrachloro-1,2-benzoquinone react with cyclopentano-and cycloheptano-fused thienopyrimidines to form the oxidative dimer of the starting material via S-S bond formation. Reaction of two equivalents of 2,2 0 -(cyclohexa-2 0 ,5 0 -diene-1,4-diylidene)dimalononitrile with thienopyrimidines afforded 3-However, the reaction of thienopyrimidines with 2,3-dicyano-1,4-naphthoquinone proceeded to afford the fused cycloalkyl-thieno form of naphtho [1,3]thiazolo[3,2-a]thieno[2,3-d]pyrimidine-6.7,12-triones. Reaction of 2-hydrazino-5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidine-4(1H)-one with dimethyl acetylenedicarboxylate and ethyl propiolate, respectively, afforded cyclohexano-fused (Z)-dimethyl 2 [(E)-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2(1H)-ylidene)hydrazono]succinate and thieno-pyrimidinotriazine. Both oxidative dimers of thienopyrimidines showed high inhibition of Hep-G2 cell growth compared with the growth of untreated control cells. Moreover, the cycloheptano-fused thiazinothienopyrimidine indicates a promising specific antitumor agent against Hep-G2 cells because its IC 50 is < 20 mM.
Reaction of 1,1,2,2‐ethenetetracarbonitrile (TCNE) with aroyl thioureas in dioxane catalyzed by few drops of piperidine, led to the corresponding 1,2,4‐oxathiazoles. Under the same reaction condition, thiosemicarbazide or thiosemicarbazone reacted with either TCNE or 1‐amino‐1,2,2‐ethene‐tricarbonitrile. The structures of the products were elucidated via NMR, IR, mass spectra, and elemental analyses. The mechanism of formation was discussed. Biological (against Gram‐positive and Gram‐negative bacteria) and antioxidant activities were tested. Some of these heterocyclic compounds showed high activity as antioxidant and antibacterial compounds. The structure–activity relationship was investigated.
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