Eco-friendly synthesis and antioxidant activity of new trifluoromethyl-substituted N-(pyrimidin-2-yl)benzo[d]thiazol-2-amines and some N-derivatives

Heterocyclizations of β-alkoxy, β-diaminoalkyl, and related β-functionalized enones (enals) with NCN-binucleophiles

“…One more type of β-alkoxy-α,β-unsaturated carbonyl compounds is represented by a few examples of alkyl-20 [36] and aryl-substituted 21 β-alkoxyenones (Scheme 7) [32]. The most well-studied compound for this category is CF3-substituted derivative 22a [64][65][66], which might be due to its chemical accessibility and the importance of the corresponding fluorinated heterocyclic products to medicinal chemistry. The known examples included the reaction of 22a with guanidine [67,68], urea [67,69], thiourea [67], isothiourea [70], formamidine [69] acetamidine, and benzamidine [71].…”

“…The known examples included the reaction of 22a with guanidine [67,68], urea [67,69], thiourea [67], isothiourea [70], formamidine [69] acetamidine, and benzamidine [71]. The variability of substituents and heterocyclization conditions of trifluoro-4-alkoxybut-3-en-2-ones 22 for the synthesis of 4-CF3-substituted pyrimidines is summarized in Table 1 [29,[66][67][68][69][72][73][74][75][76][77][78][79].…”

Haloacetylated Enol Ethers: a Way Out for the Regioselective Synthesis of Biologically Active Heterocycles

“…To remedy this, the NH ‐moiety was reacted with alkyl halides (using NaH and DMF) in an attempt to increase solubility. This was achieved, since the N ‐alkyl derivatives were soluble in chloroform, but NH ‐ derivatives were not [73] …”

In the pursuit of novel therapeutic agents: synthesis, anticancer evaluation, and physicochemical insights of novel pyrimidine-based 2-aminobenzothiazole derivatives

“…13,[15][16][17][18] Triuoromethyl-substituted N-(pyrimidin-2-yl) benzo[d]thiazol-2-amines are prepared through the cyclocondensation reaction of 2-benzothaizolyl guanidine with 4alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-triuoroalk-3-en-2-ones or 2,2,2-triuoro-1-(2-methoxycyclohexen-1-en-1-yl)ethanone. 19 Moreover, a series of pyrimidine-base 2-aminobenzothiazoles is obtained by reacting 2-benzothaizolyl guanidine with ethyl 2butylacetoacetate, diethyl ethoxymethylenemalonate, ethyl ethoxymethylenecyanoacetate, and ethoxymethylenemalononitrile in a basic medium. 20 In our previous investigations, we undertook the design and synthesis of a series of innovative benzothiazole derivatives in conjunction with pyrimidine, 21 pyridine, 22,23 purine analogues, 24 or thiophene ring.…”