Microwave-assisted three-component synthesis andin vitroantifungal evaluation of 6-cyano-5,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-ones

Abstract

The reaction of 6‐aminopyrimidin‐4‐ones 1 with benzaldehydes 2 and β‐aminocrotononitrile 3 or benzoylacetonitrile 4 under microwave irradiation in dry media yields the 6‐cyano‐5,8‐dihydropyrido[2,3‐d]‐pyrimidinones 5a‐t. The structure of the synthesized compounds was determined on the basis of nmr measurements, especially by 1H,1H−, 1H,13C COSY, DEPT and NOESY experiments. In contrast with other pyrido‐[2,3‐d]pyrimidine derivatives, these compounds did not show any antifungal in vitro activity up to 250 μg/mL.

Recent Developments in the MCRs Synthesis of Pyridopyrimidines and Spiro‐Pyridopyrimidines

“…A series of 5‐aryl‐6‐cyano‐7‐methyl‐5,8‐dihydropyrido[2,3‐ d ]pyrimidines 76 has been synthesized by Quiroga et al via MW irradiation in dry media between 6‐aminopyrimidin‐4‐ones 72 or arylaldehydes 73 and β ‐aminocrotononitrile 74 or benzoylacetonitrile 75 in 57–88% yields and 2–15 min (Scheme ).…”

An Efficient Protocol for the Synthesis of Pyrido[2,3‐d]pyrimidines in Glycerol–Water Medium: Assessment by Green Chemistry Metrics

“…The expansion of clean and efficient synthetic strategies for the design of pharmacologically important nitrogen containing heterocycles and their fused derivatives is a significant aspect of medicinal and organic chemistry . From last two decades, a great deal of consideration has been intended for synthesis of pyrido[2,3‐ d ]pyrimidine derivatives due to their attractive biological and pharmacological properties such as antibacterial, antimicrobial, analgesic, anti‐inflammatory, antitumor, cardiotonic, antifungal, antihypertensive, and calcium channel antagonists . Consequently, a number of synthetic approaches have been reported for the preparation of pyrido[2,3‐ d ]pyrimidine derivatives .…”

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

“…Recently, the pyrido[2,3‐ d ]pyrimidine derivatives have received considerable attention because of their biological and pharmacological activities such as anti‐AIDS , antifungal , antileishmanial , tuberculostatic , antimicrobial , antitumor , tyrosin ekinase , anti‐inflammatory , antiallergic , analgesic , antibronchitic , hepatoprotective , antihypertensive , calcium channel antagonists , and antibacterial .…”