ONE-POT TWO-STEP SYNTHESIS OF N3-FUNCTIONALIZED 3,4-DIHYDROPYRIMIDINONES IN THE PRESENCE OF TMSCl

@article{Quan2010ONEPOTTS,
  title={ONE-POT TWO-STEP SYNTHESIS OF N3-FUNCTIONALIZED 3,4-DIHYDROPYRIMIDINONES IN THE PRESENCE OF TMSCl},
  author={Zhengjun Quan and Rong‐Guo Ren and Yu-xia Da and Zhang Zhang and Xiaodong Jia and Cai Yang and Xicun Wang},
  journal={Heterocycles},
  year={2010},
  volume={81},
  pages={1827-1841}
}
Novel 3,4-dihydropyrimidinones modified with N3-alkyloxymethyl, aminomethyl, arylsulfonylmethyl, and azidomethyl groups can be regioselectively obtained over their isomeric N1 compounds in good yields by reaction of 3,4-dihydropyrimidinones with paraformaldehyde and alcohol, amine, sodium benzenesulfinate, and sodium azide, respectively, by a one-pot two-step strategy in the presence of chlorotrimethylsilane. The advantages of this method are the simple procedure, the high regioselectivity of… Expand
11 Citations
One-Pot Two-Step Synthesis of N3-Functionalized 3,4-Dihydropyrimidinones in the Presence of TMSCl.
N-3-substituted dihydropyrimidinones are regioselectively prepared by using the title procedure concerning the reaction between dihydropyrimidinones, paraformaldehyde (II), chlorotrimethylsilane,Expand
Copper-catalyzed click synthesis of functionalized 1,2,3-triazoles with 3,4-dihydropyrimidinone or amide group via a one-pot four-component reaction
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The molecular iodine-catalyzed three-component reaction of amides or amide derivatives, paraformaldehyde and styrenes allows for the clean generation of allylamine derivatives in good yields and highExpand
An Efficient Amide-Aldehyde-Alkene Condensation: Synthesis for the N-Allyl Amides.
TLDR
This paper shows a general protocol for Lewis acid-catalyzed N-allylation of electron-poor N-heterocyclic amides and sulfonamide via an amide-aldehyde-alkene condensation reaction, and is capable of preparing the Naftifine motif from N-methyl-1-naphthamide or methyl (naphthalene- 1-ylmethyl)carbamate in a one-pot manner. Expand
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A domino desulfitative coupling/acylation/hydration process to synthesize C-2-(2-oxo-2-phenylethylidene)- and N-3-carbonyl-substituted pyrimidines by unprecedented CC and CN cross-coupling reactionsExpand
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Stereoselective synthesis of the right-hand heteroaromatic macrocycle of diazonamide A features C16-C18 bond formation in the Suzuki-Miyaura cross-coupling and atropodiastereoselective Dieckmann-typeExpand
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References

SHOWING 1-10 OF 29 REFERENCES
Metalation of Biginelli compounds. A general unprecedented route to C-6 functionalized 4-aryl-3,4-dihydropyrimidinones.
4-Aryl-6-methyl-3,4-dihydro-2(1H)-pyrimidinone esters (DHPMs) readily undergo metalation at the C-6 methyl (vinylogous ester) position on treatment with lithium diisopropylamide at -10 degrees C. TheExpand
A practical and green approach toward synthesis of N3-substituted dihydropyrimidinones: using Aza-Michael addition reaction catalyzed by KF/Al2O3.
A simple and efficient method for the synthesis of N3-substituted 3,4-dihydropyrimidinones by aza-Michael addition reactions of 3,4-dihydropyrimidinones to alpha,beta-ethylenic compounds catalyzed byExpand
A mild and practical method for the regioselective synthesis of N-acylated 3,4-dihydropyrimidin-2-ones. New acyl transfer reagents
The treatment of 3,4-dihydropyrimidin-2-ones with n-BuLi at −78 °C, followed by quenching with various electrophiles furnished N3-substituted derivatives, regioselectively. Further, N1,N3-diacylExpand
N1-Alkylated 3,4-dihydropyrimidine-2(1H)-ones: Convenient one-pot selective synthesis and evaluation of their calcium channel blocking activity.
It has been found that selective N1-alkylation of 3,4-dihydropyrimidine-2(1H)-ones can be achieved under solvent-less, mild phase transfer catalytic (PTC) conditions with tetrabutylammonium hydrogenExpand
Michael additions of dihydropyrimidines and 2-amino-1,3,4-thiadiazoles to α,β-ethylenic compounds: using polyethylene glycols as a green reaction media
Abstract Polyethylene glycol (PEG) was found to be an inexpensive, non-toxic, and effective medium for the Michael additions of 3,4-dihydropyrimidines to α,β-ethylenic compounds to provideExpand
Highly versatile solid phase synthesis of biofunctional 4-aryl-3,4-dihydropyrimidines using resin-bound isothiourea building blocks and multidirectional resin cleavage.
  • C. Kappe
  • Chemistry, Medicine
  • Bioorganic & medicinal chemistry letters
  • 2000
TLDR
A series of pharmacologically active, functionalized 4-aryl-3,4-dihydropyrimidine-5-carboxylates (DHPMs) are prepared by a versatile novel solid phase approach employing multidirectional resin cleavage strategies. Expand
Synthesis and reactions of Biginelli-compounds. Part 23. Chemoenzymatic syntheses of enantiomerically pure 4-aryl-3,4-dihydropyrimidin-2(1H)-ones
Enantiomerically pure dihydropyrimidones (DHPMs) were prepared by lipase-catalyzed enzymatic resolution of two types of activated DHPM esters. In the first model series, pivaloyloxymethyl-activatedExpand
Indium(III) bromide-catalyzed preparation of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction
Abstract Indium(III) bromide efficiently catalyzes the three-component coupling of β-keto esters, aldehydes and urea (or thiourea) to afford the corresponding dihydropyrimidinones. This new protocolExpand
Demonstration of the feasibility of a direct solid-phase split-pool Biginelli synthesis of 3,4-dihydropyrimidinones.
TLDR
Formation of only one kind of Biginelli product per bead demonstrated the feasibility of a solid-phase non-Atwal two-step split-and-pool synthesis of 3,4-dihydropyrimidinones. Expand
Biocatalysis for the preparation of optically active β-lactam precursors of amino acids
Abstract Enantioselective acylation of N -hydroxymethylated β-lactams in the presence of Pseudomonas sp. lipase afforded optically active precursors for the preparation of (1 R ,2)- and (2 S ,2 RExpand
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