2001
DOI: 10.1016/s0960-894x(01)00506-6
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Combinatorial synthesis of SSAO inhibitors using sonogashira coupling: SAR of aryl propargylic amines

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Cited by 10 publications
(8 citation statements)
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“…Similarly, the coupling of iodoarenes with propargylamines has been widely exploited by Conn et al for the synthesis of SSAO inhibitors in a combinatorial fashion. In this case, the Sonogashira coupling was carried out in THF/TEA at room temperature with tetrakis­(triphenylphosphine)­palladium(0) and copper iodide as catalysts . Generally, the Sonogashira reaction is used to introduce a Boc-protected propargylamine substituent, which can then be converted to other functionalities via oxidation/reduction.…”
Section: Reactivity Of Propargylaminesmentioning
confidence: 99%
See 1 more Smart Citation
“…Similarly, the coupling of iodoarenes with propargylamines has been widely exploited by Conn et al for the synthesis of SSAO inhibitors in a combinatorial fashion. In this case, the Sonogashira coupling was carried out in THF/TEA at room temperature with tetrakis­(triphenylphosphine)­palladium(0) and copper iodide as catalysts . Generally, the Sonogashira reaction is used to introduce a Boc-protected propargylamine substituent, which can then be converted to other functionalities via oxidation/reduction.…”
Section: Reactivity Of Propargylaminesmentioning
confidence: 99%
“…In this case, the Sonogashira coupling was carried out in THF/TEA at room temperature with tetrakis(triphenylphosphine)palladium(0) and copper iodide as catalysts. 548 Generally, the Sonogashira reaction is used to introduce a Boc-protected propargylamine substituent, which can then be converted to other functionalities via oxidation/reduction. The terminal alkyne can also be used in other Sonogashira couplings or alternatively react with amines to afford imines.…”
Section: Various Metal-catalyzed Transformations Of Propargylamines S...mentioning
confidence: 99%
“…The coupling reaction of 4-bromotoluene and 4-bromoanisole with cyclohexylacetylene afforded disubstituted alkynes 4g and 4o in a 40 and 37% yield, respectively (Table 3, entries 3 and 9). A 61% yield of the semicarbazide-sensitive amine oxidase (SSAO) inhibitor [20] 4f was obtained when 4-bromoanisole reacted with N,N-dimethyl-2-propynylamine under the optimized conditions (Table 3, entry 8). A low 30% yield of alkyne 4h was obtained by reaction of 4-bromoanisole with 1-dodecyne (Table 3, entry 10).…”
Section: Resultsmentioning
confidence: 99%
“…plasma SSAO in micromolar concentration. A two-point model interpreted these results: the amino group co-ordinates to the copper(II) and the phenyl group forms a π-complex with topa quinone [72].…”
Section: Propargylamine Derivativesmentioning
confidence: 94%