2012
DOI: 10.1007/s10593-012-1061-8
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Features of the base-catalyzed reaction of 1-vinyl-4,5-dihydro-1H-benzo[g]indole-2-carbaldehyde with phenylacetylene

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Cited by 3 publications
(4 citation statements)
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“…After comparative analysis of the available literature data [21–23] and consequent optimization of the reaction conditions we have found that the superbasic catalytic composition NaOH/EtOH/DMSO (the molar ratio 1:1.6:13.6) and a temperature of 7–10 °C (Table 1), which is by ca. ten degrees higher than recommended in the patent [22], are appropriate for the efficient ethynylation of 1-vinylpyrrole-2-carbaldehydes with acetylene.…”
Section: Resultsmentioning
confidence: 99%
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“…After comparative analysis of the available literature data [21–23] and consequent optimization of the reaction conditions we have found that the superbasic catalytic composition NaOH/EtOH/DMSO (the molar ratio 1:1.6:13.6) and a temperature of 7–10 °C (Table 1), which is by ca. ten degrees higher than recommended in the patent [22], are appropriate for the efficient ethynylation of 1-vinylpyrrole-2-carbaldehydes with acetylene.…”
Section: Resultsmentioning
confidence: 99%
“…ten degrees higher than recommended in the patent [22], are appropriate for the efficient ethynylation of 1-vinylpyrrole-2-carbaldehydes with acetylene. As alkali metal hydroxide for the superbase composition we have chosen NaOH since the more basic KOH was shown to promote a subsequent chalcone formation after ethynylation of 4,5-dihydrobenzo[ g ]indole-2-carbaldehyde (which contains a pyrrole-2-carbaldehyde moiety) with phenylacetylene [21]. As shown on the example of benzaldehyde [22], other ratios of the catalytic composition give inferior yields of the corresponding acetylenic alcohol.…”
Section: Resultsmentioning
confidence: 99%
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“…However, these A 3 -coupling systems require the use of transition-metal catalysts and (super)­stoichiometric amounts of amines. Interestingly, when the Favorskii reaction, i.e., the addition of terminal alkynes to carbonyl compounds to afford propargylic alcohols using strong bases, e.g., KOH, , t BuOK, , and Bu 4 NOH, is performed using an aromatic aldehyde as the substrate, the side reaction to produce an α,β-unsaturated carbonyl compound occurs . This side reaction can be regarded as a transition-metal-free formal hydroacylation; however, these systems require strong basic conditions, and the substrate scopes are quite limited.…”
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confidence: 99%