Solvent-free microwave synthesis of novel 6-hydroxypyrimidin-4(1H)-one derivatives using arylmalonates

Chichetti, Stephanie M.; Ahearn, Sean P.; Adams, Bruce; Rivkin, Alexey

doi:10.1016/j.tetlet.2007.08.134

Cited by 12 publications

(7 citation statements)

References 14 publications

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“…With the demand and development of the pharmaceutical industry, there are many classical methods to synthesize pyridopyrimidines [7] . For instance, a microwave‐assisted method was reported for the synthesis of 4‐hydroxy‐3‐phenyl‐2 H ‐pyrido[1,2‐ a ] pyrimidin‐2‐one and variants using activated arylmalonates with very high temperature (Scheme 1a) [8] . Another method is start from 2‐aminopyridine and bromobenzene, the target product was synthesized by multi‐step reaction in a low yield (Scheme 1b) [9] .…”

Section: Figurementioning

confidence: 99%

Cascade Wolff Rearrangement and Double N‐Acylation: A Cyclization of α‐Diazoketones with 2‐aminopyridines or 3‐aminopyrazoles to Synthesize Fused Pyrimidinediones

Ren,

Zhou,

Song

et al. 2023

Adv Synth Catal

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A cascade Wolff rearrangement and double N‐acylation reaction has been developed for the synthesis of fused pyrimidinediones in one‐pot under air. These reactions were performed with α‐diazoketones and 2‐aminopyridines or 3‐aminopyrazoles under catalyst‐ and additive‐free conditions. The protocol avoided traditional purification procedures, such as organic solvent extraction and column chromatography. The synthesis of biologically active molecules and gram‐scale experiment demonstrated the potential applications of this reaction.

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Section: Figurementioning

confidence: 99%

Cascade Wolff Rearrangement and Double N‐Acylation: A Cyclization of α‐Diazoketones with 2‐aminopyridines or 3‐aminopyrazoles to Synthesize Fused Pyrimidinediones

Ren,

Zhou,

Song

et al. 2023

Adv Synth Catal

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“…A well‐known procedure for the synthesis of this class of compounds remain the coupling of Baylis–Hillman adduct or its derivatives with 2‐aminopyridines . Other methods to construct this skeleton involves treatment of 2‐aminopyridines with alkynoate esters or aryl malonates, or by cyclization of N ‐(1,3‐dioxobutyl)‐2‐aminopyridines (Scheme ) . The major limitation for the synthesis of this scaffold can be ascribed to the relative lack of synthetic flexibility for their construction.…”

Section: Introductionmentioning

confidence: 99%

Metal and Solvent‐Free Synthesis of 2H‐Pyrido[1,2‐a]pyrimidin‐2‐ones Catalyzed by Elemental Sulfur

et al. 2019

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The efficiency of elemental sulfur for the synthesis of 2H‐pyrido[1,2‐a]pyrimidin‐2‐ones has been demonstrated. This strategy involves coupling of 2‐aminopyridines and β‐oxo esters under neat condition in the absence of external oxidant. The reaction does not require pre‐functionalization of the substrates, thus making it an alternate approach for the synthesis of 2H‐pyrido[1,2‐a]pyrimidin‐2‐ones. The reaction was tolerant to several substituted 2‐aminopyridines and β‐oxo esters.

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“…23, 24 Chichetti et al have reported the solvent-free microwave synthesis of novel 6-hydroxypyrimidin-4(1H)-one derivatives using arylmalonates. 25 Su et al have reported the synthesis of these heterocycles by using Vilsmeier reagent. 26 Above methods require, activated Baylis-Hillman adducts, 21, 27 microwave assistance, 22, 25 and added reagents.…”

Section: Introductionmentioning

confidence: 99%

“…25 Su et al have reported the synthesis of these heterocycles by using Vilsmeier reagent. 26 Above methods require, activated Baylis-Hillman adducts, 21, 27 microwave assistance, 22, 25 and added reagents. 23, 24, 26 In our effort to develop domino methodologies to synthesize novel heterocycles, 28, 29 herein, we present hexafluoroisopropanol (HFIP) mediated sustainable design, reagent or catalyst free, and negligible by product formation for the synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones by using 2-aminopyridines and unactivated BH-adducts.…”

Section: Introductionmentioning

confidence: 99%

Hexafluoroisopropanol mediated benign synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones by using a domino protocol

et al. 2017

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Domino strategy has been used for the synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones. Four sequential reactions: aza-Michael addition, water elimination, intramolecular acyl substitution, and [1,3]-H shift were observed in this domino protocol. Hexafluoroisopropanol is used as a promotor and recyclable solvent in this cascade process. Availability of inexpensive 2-aminopyridines and wide variety of Michael acceptors such as commercially available acrylates and unactivated Baylis-Hillman adducts makes this methodology a huge reservoir of novel fused N-heterocycles as bioactive and potential therapeutic agents. The reaction mechanism has been proposed and rationalized by density functional theory calculation. Products are obtained up to 95% yield.

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Solvent-free microwave synthesis of novel 6-hydroxypyrimidin-4(1H)-one derivatives using arylmalonates

Cited by 12 publications

References 14 publications

Cascade Wolff Rearrangement and Double N‐Acylation: A Cyclization of α‐Diazoketones with 2‐aminopyridines or 3‐aminopyrazoles to Synthesize Fused Pyrimidinediones

Cascade Wolff Rearrangement and Double N‐Acylation: A Cyclization of α‐Diazoketones with 2‐aminopyridines or 3‐aminopyrazoles to Synthesize Fused Pyrimidinediones

Metal and Solvent‐Free Synthesis of 2H‐Pyrido[1,2‐a]pyrimidin‐2‐ones Catalyzed by Elemental Sulfur

Hexafluoroisopropanol mediated benign synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones by using a domino protocol

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