The Reformatsky analogous reaction for the synthesis of novel β-thioxoestersviausing aroyl isothiocyanates under solvent-free ball milling and conventional conditions

Abstract

The Reformatsky analogous reaction between aroyl isothiocyanates and α-haloesters using metallic zinc to form β-thioxoesters via ball milling and conventional techniques.

New pyrazolo[3,4-d]pyrimidine derivatives as EGFR-TK inhibitors: design, green synthesis, potential anti-proliferative activity and P-glycoprotein inhibition

“…Our current research is concerned with the utility of N -(4-(4-chlorobenzylidene)-4 H -pyrazol-3-yl)benzamide (1) in the synthesis of new substituted fused pyrimidine derivatives under conventional and green conditions as part of our interest in the synthesis of a wide range of heterocyclic systems with biological applications. 34–37…”

“…Our current research is concerned with the utility of N-(4-(4chlorobenzylidene)-4H-pyrazol-3-yl)benzamide (1) in the synthesis of new substituted fused pyrimidine derivatives under conventional and green conditions as part of our interest in the synthesis of a wide range of heterocyclic systems with biological applications. [34][35][36][37] The starting chemical, N-(4-(4-chlorobenzylidene)-5-oxo-4,5dihydro-1H-pyrazol-3-yl)benzamide (1), was synthesized according to an earlier reported procedure 38 under different chemical reaction conditions. Thus, reuxing of compound 1 with ethanolic solution of thiourea in the presence of catalytic amount of sodium ethoxide or under free solvent fusion technique to afford the target compound N-(4-(4-chlorophenyl)-6thioxo-6,7-dihydro-5H-pyrazolo [3,4-d]pyrimidin-3-yl)benzamide (2) with a benecial yield, which was used as a key starting material as illustrated in (Scheme 1).…”

Isothiocyanates (in situ) and sulfonyl chlorides in water for N-functionalization of bicyclic amidines: access to N-alkylated γ-/ω-lactam derivatized thiourea and sulfonamides

“…To explore the utility of this chemical reaction, we investigated the synthesis of aroyl thiourea compounds featuring cyclic amide functionalities. We synthesized aroyl isothiocyanates 13 , 14 which were subsequently employed in situ for nucleophilic reactions with either DBN or DBU (Table 3). However, when we utilized DBN as the base, our observations revealed a mixture of products, consisting of aroyl thioureas ( 14 ) and amides ( 15 ) with an approximately 1 : 1 ratio.…”

“…We synthesized aroyl isothiocyanates 13, 14 which were subsequently employed in situ for nucleophilic reactions with either DBN or DBU (Table 3). However, when we utilized DBN as the base, our observations revealed a mixture of products, consisting of aroyl thioureas (14) and amides (15) with an approximately 1 : 1 ratio. In contrast, when we employed DBU as the nucleophilic reagent, we exclusively obtained the corresponding amides (16).…”

New 1,3,4-thiadiazoles as potential anticancer agents: pro-apoptotic, cell cycle arrest, molecular modelling, and ADMET profile

“…As a part of our ongoing research that aims at developing simple and efficient synthetic techniques for the synthesis of novel heterocyclic compounds with potential anticancer applications, [21][22][23][24][25][26][27][28][29][30][31] the present study reported the synthesis of numerous new substituted 1,3,4-thiadiazole derivatives incorporating benzene moiety. N-(5-Amino-1,3,4-thiadiazol-2-yl) benzamide (2) was synthesized as a sole product through reaction of benzoylisothiocyanate with thiosemicarbzide in dry acetonitrile and then underwent cyclization according to the previously published methodology [32][33][34][35][36] (Scheme 1). Treatment of compound 2 with ethyl cyanoacetate in the presence of a catalytic amount of triethylamine afforded N-(5-(2-cyanoacetamido)-1,3,4-thiadiazol-2-yl)benzamide (3) in a high yield, which was used as a key starting material (Scheme 1).…”