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Selič, Lovro; Jakse, Renata; Lampič, Kristina; Golič, L.; Golič‐Grdadolnik, Simona; Stanovnik, B.

doi:10.1002/1522-2675(20001004)83:10<2802::aid-hlca2802>3.0.co;2-9

Cited by 57 publications

(20 citation statements)

References 11 publications

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“…In contrast, reactions with t-BAE result solely in the formylation product, the reagent being inefficient at transfer of a methyl group (eq 34). 112, 113 The chemistry of methyl orthocarboxylates, including DMF-DMAs, as methylating agents has recently been reviewed. …”

Section: Bnhnmentioning

confidence: 99%

t-Butoxybis(dimethylamino)methane

Kantlehner

Bowers

2007

Encyclopedia of Reagents for Organic Synthesis

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1 tert-Butoxybis(dimethylamino)methane 1 CH RO NMe 2 NMe 2 (1; R = t-Bu) (t-BAE) [5815-08-7] C 9 H 22 N 2 O (MW 174.33) InChI = 1/C9H22N2O/c1-9(2,3)12-8(10(4)5)11(6)7/h8H,1-7H3 InChIKey = HXRAMSFGUAOAJR-UHFFFAOYAR (2; R = Me) (MAE) [1186-70-5] C 6 H 16 N 2 O (MW 132.24) InChI = 1/C6H16N2O/c1-7(2)6(9-5)8(3)4/h6H,1-5H3 InChIKey = NCIMAYPZWJQYGN-UHFFFAOYAO (aminal esters reactive as aminomethylenating reagents (formylating reagents) for CH 2 -and NH 2 -acidic compounds. The t-butyl analog is somewhat more reactive than the methyl derivative; bis(dimethylamino)carbene can be generated from both compounds) Alternate Name: Bredereck's reagent. Physical Data: (1) bp 50-52 • C/12 mmHg; n 20 D = 1.4250. (2) bp 128 • C/760 mmHg; 32-33 • C/25 mmHg; n 20 D = 1.4158. Solubility: miscible with nonpolar aprotic waterfree solvents (benzene, toluene, cyclohexane, diethyl ether, etc.); react with protic solvents like water (hydrolysis to DMF) or alcohols (alcoholysis affords DMF acetals). Even common solvents like acetonitrile or acetone which are weakly CH-acidic react with the aminal esters on heating. Form Supplied in: colorless to weak yellow, strong aminesmelling liquids. Analysis of Reagent Purity: the best method is 1 H NMR spectroscopic examination of a neat sample. Handling, Storage, and Precautions: both compounds should be handled in a fume hood, with strict exclusion of atmospheric moisture. They should be stored in tightly sealed containers in a refrigerator under an atmosphere of dry nitrogen or argon.Introduction. Alkoxybis(dimethylamino)methanes can be obtained in good yields from N,N,N ,N -tetraalkylformamidinium salts and alcohol-free alkoxides. 2 The reactions have to be conducted in inert, strictly anhydrous solvents like cyclohexane, hexane, ether, or THF, in which unfortunately both reagents are insoluble. As a consequence it is necessary to use relatively large amounts of the solvent and long reaction times (eq 1). In the patent literature it is claimed that by the use of a mixture of DMF and mesitylene as solvent, the yields can be improved to about 95%. 3 In another method, 4 bis(dimethylamino)acetonitrile is used as the starting compound. Alcohol-free alkoxides suspended in absolute ether substitute the cyano group to give the corresponding aminal ester (eq 2). In contrast to the aforementioned method,

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Section: Bnhnmentioning

confidence: 99%

t-Butoxybis(dimethylamino)methane

Kantlehner

Bowers

2007

Encyclopedia of Reagents for Organic Synthesis

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“…Both methods are stereoselective and can afford various types of aplysinopsin analogs in moderate or good overall yields. In this case, hydantoin derivatives 12 are transformed with tert-butoxy-bis(dimethylamino)methane (Bredereck's reagent) or N,N-dimethylformamide dimethyl acetal (DMFDMA) into the corresponding (Z ) -5 -[(dimethylamino) methylidene] imidazo-lidine-2,4-diones 26, which react further with indole derivatives to give aplysinopsin derivatives 8g-w in 10-81% yields [25,26]. Treatment of 24 with urea, N,N'-diphenylthiourea, or an isothiocyanate affords aplysinopsin 8 and thioaplysinopsin derivatives 9 in 10-96% yields [25].…”

Section: (Scheme 3)mentioning

confidence: 99%

The Synthesis Aplysinopsins, Meridianines, and Related Compounds

Stanovnik¹,

Svete

2005

MROC

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Aplysinopsins and meridianines have been isolated from various marine organisms. They exhibit interesting biological activity, such as cytotoxicity and neurotransmission effects. Various synthetic approaches towards these two classes of natural products and their synthetic analogs have been developed. Most syntheses of aplysinopsins, meridianines, and their analogs are based either on coupling of two heterocyclic moieties via the methylidene bridge, or on heterocyclization of indoles, functionalized at position 3.

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“…13 They are antagonists of many receptors including the neurokinin-1 receptor 14 and the dopamine receptor. 15 They were applied as intermediates in the synthesis of many natural products, such as biotin, 16 slagenins, 17 axinohydantoins, 18 oroidin-derived alkaloids, 19 aplysinopsins, 20 Lancetta-derived alkaloid carcaridine A, 21 and others. Due to their importance, many methods have been developed for the construction of the imidazole ring.…”

Section: Introductionmentioning

confidence: 99%