A Facile Synthesis of New Pyrazolo[3,4‐d]pyrimidine Derivatives via a One‐Pot Four‐Component Reaction with Sodium Acetate Supported on Basic Alumina as Promoter

Abstract

An efficient one‐pot procedure for the synthesis of 3‐amino‐6‐aryl‐2‐phenylpyrazolo[3,4‐d]pyrimidine derivatives, through the reaction of aldehydes, malononitrile, benzamidine hydrochloride, and hydrazine hydrate in the presence of basic alumina‐supported sodium acetate (AcONa/Al2O3) under reflux conditions, is reported. This protocol has some advantages, including the use of a simple and one‐pot synthetic approach to attain pyrazolo[3,4‐d]pyrimidine directly from four readily available starting materials, simple workup, high overall yields of the products, and the simultaneous conversion of a NO2 to an amino group, offering an opportunity to synthesize more complex structures.

Pyrazolopyrimidines as Anticancer Agents; Syntheses and Mode of Action (Review Article)

“…In 2013, 4d]pyrimidine derivatives 30 by reacting 4-amino-6-aryl-2-phenyl-pyrimidine-5carbonitrile derivatives 29 and hydrazine hydrate in ethanol under reflux (Rostamizadeh et al, 2013). In a promising procedure, Rostamizadeh et al debuted a one-pot (Fig.…”

Multicomponent Synthesis of Purines and Pyrimidines: From the Origin of Life to New Sustainable Approaches for Drug‐Discovery Applications

“…The authors demonstrated that both electron-donating and electron-withdrawing substituents on the aromatic ring of aldehydes were well tolerated. [80] Another reaction for pyrimidine synthesis was proposed by Ramin Ghorbani-Vaghei et al They improved the otherwise classical protocol of the one-pot synthesis of pyrimidine derivatives from triethoxymethane 151, ammonium acetate and various ketone derivatives 150, using N,N,N',N'-Tetrabromobenzene-1,3-disulfonamide as catalyst (18 mol) under solvent-free conditions (Scheme 53). [81] In the same years, a useful regioselective synthesis of highly functionalized N-fused imidazo experiments have demonstrated that both CuI and Ag 2 CO 3 catalysts were necessary for the good outcome of the reaction.…”

“…Reacting in one pot, aldehydes 147 , malononitrile 62 , benzamidine hydrochloride 148 , and hydrazine hydrate in the presence of basic alumina‐supported sodium acetate (AcONa/Al 2 O 3 ) under reflux conditions, yielded the desired product 149 (Scheme 52). The authors demonstrated that both electron‐donating and electron‐withdrawing substituents on the aromatic ring of aldehydes were well tolerated [80] …”

Facile Synthesis of Some Novel Tetrasubstituted 2,4‐Diaminopyrimidine Derivatives in Aqueous Glucose Solution as a Fully Green Medium and Promoter

“…Recently, numerous synthetic methods have been reported in the literature for the synthesis of these valuable heterocycles through ring construction of linear starting materials. The most important strategy toward the synthesis of pyrimidine derivatives having 4‐amino substituent includes the one‐pot three‐component reaction of malononitrile, aromatic aldehydes, and amidine derivatives using a basic catalyst . Despite the fact that these methods all have their advantages, the use of basic catalyst mostly metal oxides seems necessary to promote the reaction.…”