A Green Synthesis of 7‐amino‐5‐(4‐aroyl)‐1,3‐dimethyl‐2,4‐dioxo‐1,2,3,4,5,8‐hexahydropyrido[2,3‐d]pyrimidine‐6‐carbonitrile Derivatives by a One‐pot Three‐component Reaction

Abstract

The synthesis of polyfunctionalized 7‐amino‐5‐(4‐aroyl)‐1,3‐dimethyl‐2,4‐dioxo‐1,2,3,4,5,8‐hexahydropyrido[2,3‐d]pyrimidine‐6‐carbonitrile derivatives by a green approach was achieved via one‐pot three‐component reaction of arylglyoxals, malononitrile, and 1,3‐dimethyl‐6‐aminouracil in the presence of urea as organocatalyst in EtOH:H2O (1:1) at 60°C. This protocol provides a mild and fast procedure to structurally diverse bicyclic pyridopyrimidines in good to excellent yields.

One-pot, three-component synthesis of pyrrolo[2,3-d]pyrimidine derivatives

“…In attempting to develop a simple, one-pot and short reaction pathway for the synthesis of various heterocyclic compounds, we reported earlier the synthesis of pyrazolo [3,4-d]pyridines, pyrazolo[3,4-b]qunolin-5-ones and pyrazolo [4',3':5,6] 2,3,4,5,8-hexahydropyrido[2,3d]pyrimidine -6-carbonitriles, pyrrolo[3,2-d]pyrimidines [17][18][19][20][21][22][23].…”

“…Elemental analyses were performed using a Leco Analyzer 932. The arylglyoxals were prepared as their hydrates by oxidation of the corresponding acetophenones with SeO2 [22].…”

“…In continuation of our interest in the synthesis of new heterocyclic compounds via one-pot, multicomponent reactions [17][18][19][20][21][22][23], herein we report a convenient and rapid method for the synthesis of pyrrolo[2,3-d]pyrimidine derivatives by one-pot three-component reactions using arylglyoxals 1a-d, 6-amino-1,3-dimethyluracil (2) and barbituric acid derivatives 3a-c in the presence of a catalytic amount of TBAB (5 mol%) at 50 °C in ethanol.…”

An overview on synthetic and pharmaceutical prospective of pyrido[2,3‐d]pyrimidines scaffold

“…On the other hand, the traditional approaches having sufficient importance in MCR and Hantzsch, Biginelli type reaction results in substituting pyridopyrimidine derivatives from the last decades. Javahershenas and Khadafy obtained a desired product 4 by using single step multicomponent reaction of arylglyox-als1, malononitrile 2, and 1,3-dimethyl-6-aminouracil 3 in the existence of urea as catalyst in ethanol: water (1:1) reflux at 60°C (Scheme 1) (Javahershenas & Khalafy, 2017).…”

One‐pot, Three‐component Synthesis of a Series of New Bis‐pyrrolo[2,3‐d]pyrimidines in the Presence of TPAB under Reflux Conditions

“…In continuation of our interests in the synthesis of new heterocyclic compounds by one‐pot, multicomponent reaction , herein, we report a convenient and rapid method for the synthesis of a series of new bis‐pyrrolo[2,3‐ d ]pyrimidine derivatives by a one‐pot, three‐component reaction of 1,4‐phenylene‐bis‐glyoxal, 6‐aminouracils, and dimedone or barbituric acid derivatives in the presence of TPAB (5 mol%) in ethanol under reflux conditions in high yields (90–96%). It seems that, the substituted bis‐pyrrolo[2,3‐ d ]pyrimidines could be biologically and pharmacologically more active than pyrrolo[2,3‐ d ]pyrimidine derivatives owing to having two heterocyclic moieties in their molecules.…”