An Efficient Synthesis of Tetracyclic Pyrano[2,3‐d]pyrimidines

Abstract

A series of pyrano[2,3‐d]pyrimidine derivatives have been synthesized by the reaction of 2‐amino‐3‐cyano‐4H‐pyrans and acetic anhydride with acid catalyst . This method is very efficient because of short reaction times and easy work‐up, and it provides an efficient and promising synthetic strategy for the construction of the tetracyclic pyrano[2,3‐d]pyrimidine skeleton. The X‐ray crystal structures of products are confirmed, and the possible mechanism is provided in this paper.

Synthesis, biological evaluation and induced fit docking simulation study ofd-glucose-conjugated 1H-1,2,3-triazoles having 4H-pyrano[2,3-d]pyrimidine ring as potential agents against bacteria and fungi

“…According to entry 1, it is clear that in this reaction, acetic anhydride (and acetyl chloride) is the acylation agent for converting the 2-amino group to 2-acetamido one, 41 sulphuric acid is the cyclo-condensation agent, and in the formation of 5a via Dimroth rearrangement, 8 we decided to use PPA (entry 4) and POCl 3 (entry 5) instead conc. sulphuric acid in the reaction of ester 4a to acetic acid.…”

Synthesis and Cytotoxic Evaluation of New Fluoro and Trifluoromethyl Substituents Containing Chromeno[2,3‐d]pyrimidines

“…[28] Moreover, another efficient and promising synthetic strategy for the construction of chromeno [2,3-d]pyrimidine skeleton using the reaction of 2amino-3-cyano-4H-chromenes with different reagents such as anhydrides, carboxylic acids, formamide, urea, and formamidine acetate have been reported. [29] Although chromeno [2,3-d]pyrimidines and fluorinated molecules are of great interest, the synthesis and biological evaluation of these moieties into a single molecule have rarely been studied. Therefore, as a continuation of our interests on the synthesis of bioactive heterocycles, [30] and multicomponent domino reactions, herein we report the synthesis of new fluorinated chromeno [2,3-d]pyrimidines 10 a-l and evaluation of their cytotoxic activity against several cancer cell lines.…”