- N-alkylation of 2-methyl-2-imidazolines by phase transfer catalysis without solvent
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1-Alkyl-2-methyl-2-imidazolines were obtained in good to excellent yields by alkylation of 2-methyl-2-imidazoline with organic halides in the presence of phase transfer catalysis and absence of solvent.
- Chen, Xu,Wang, Xiaolun,Wang, Hui,Lian, Hongzhen,Pan, Yi,Shi, Yaozeng
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- A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes
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The reaction of 1,2-disubstituted 2-imidazolines with electron-deficient alkynes proceeds as a pseudo-three-component process and forms imidazolidines with an N-vinylpropargylamine fragment. Heating the resulting imidazolidines in xylene on air leads to a
- Festa, Alexey A.,Golantsov, Nikita E.,Golubenkova, Alexandra S.,Varlamov, Alexey V.,Voskressensky, Leonid G.
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supporting information
(2020/06/29)
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- Electrophilically activated nitroalkanes in reaction with aliphatic diamines en route to imidazolines
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A novel synthetic methodology for the assembly of imidazolines via an unusual reaction between nitroalkanes and aliphatic 1,2-diamines in the presence of phosphorous acid is described. In contrast to the related highly efficient preparation of benzimidazoles from aromatic amines, this process represents a major synthetic challenge and for a long time was elusive. Analysis of the method limitations is provided.
- Aksenov, Alexander V.,Aksenov, Nicolai A.,Arutiunov, Nikolai A.,Malyuga, Vladimir V.,Ovcharov, Sergey N.,Rubin, Michael
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p. 39458 - 39465
(2019/12/14)
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- Coenzyme-inspired chemistry 1: The C-2 alkylation of 4,5-dihydroimidazoles
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Alkylation of 4,5-dihydroimidazoles at C-2 is accomplished using a double umpolung of the reactivity of that position, via sulfenylation of a nucleophilic C-2 lithio-species and substitution using an alkyl nucleophile. Arylation via unexpected sulfide con
- Jones, Raymond C.F.,Nichols, John R.
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p. 4114 - 4119
(2013/06/27)
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- Alkylation of an imidazolidine enaminoester: A new sequence for the c(α)-alkylation of 4,5-dihydroimidazoles
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1-Benzyl-2-(ethoxycarbonyllmethylene)-2,3,4,5-tetrahydroimidazole undergoes preferred C-alkylation with halogenonakanes, dihalogenoalkanes and epoxides: subsequent removal of of the ethoxycarbonyl group provides a new route to 2-alkyl-4,5-dihydroimidazoles. 1,3-Dihalogenoalkanes afford imidazo[1,2-a]pyridines via C,N-dialkylation.
- Jones, Raymond C. F.,Patel, Pravin,Hirst, Simon C.,Turner, Ian
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p. 11781 - 11790
(2007/10/03)
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- 2-Methyl-4,5-dihydroimidazole as a Doubly Nucleophilic Unit: Preparation of Dihydroimidazole Azaprostanoids
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2-Methyl-4,5-dihydroimidazole is incorporated as a doubly nucleophilic synthon, by successive alkylations at N-1 and C-2(Me), into monocyclic 9,12- and 8,11-diazaprostanoids containing the dihydroimidazole moiety. 2-Methyl-3a,4,7,7a-tetrahydrobenzimidazole is prepared (from 1,2,3,6-tetrahydrophthalic anhydride) and elaborated in the same way into a diazaprostacyclin precursor.
- Jones, Raymond C. F.,Schofield, Julie
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p. 375 - 383
(2007/10/02)
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- Tetrahydrofolate coenzyme models: Imidazolines as nucleophilic C1-transfer reagents
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1-Benzyl-2-imidazoline is deprotonated at C-2 and alkylated by a sulphenylation-substitution sequence (to complete a formal C1-transfer), whereas arylation occurs by an unusual sulphenylation-sulphide contraction pathway.
- Jones,Nichols
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p. 1767 - 1770
(2007/10/02)
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- CONDENSATION REACTIONS OF α-LITHIO-IMIDAZOLINES: PREPARATION AND CONJUGATE ADDITIONS OF 2-ALKENYL-2-IMIDAZOLINES.
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Whereas 1-benzyl-2-lithiomethyl-2-imidazoline undergoes reversible 1,2-addition to aldehydes and ketones, a derived phosphonate salt affords the condensation products, 2-(1-alkenyl)-2-imidazolines; the latter undergo conjugate addition with carbon nucleop
- Jones, Raymond C. F.,Anderson, Michael W.,Smallridge, Mark J.
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p. 5001 - 5004
(2007/10/02)
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- Dihydroimidazoles in Synthesis: C-Acylation of Lithiodihydroimidazoles
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1-Benzyl-2-methyl-4,5-dihydroimidazole has been lithiated and C-acylated by reaction with esters and a nitrile.The products do not exist as 2-(2-oxoalkyl)dihydroimidazoles but as the alternative tautomers, as indicated by spectroscopic and crystallographi
- Anderson, Michael W.,Begley, Michael J.,Jones, Raymond C. F.,Saunders, John
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p. 2599 - 2602
(2007/10/02)
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