Pyrrole chemistry. XXIII. The cyanation of substituted pyrroles with chlorosulfonyl isocyanate (CSI). New syntheses of pyrrole-3-carbonitriles

Loader, C. E.; Anderson, Hugh J.

doi:10.1139/v81-384

Cited by 52 publications

(17 citation statements)

References 4 publications

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“…Substrates 5 and 8 were obtained from Sigma–Aldrich in the highest purity available. Syntheses of substrates 6 11 and 7 ,12 as well as other substrates screened, and their precursors,13 were done according to literature procedures and can be found in the Supporting Information. Thin layer chromatography was carried out with precoated aluminium silica gel 60 F 254 plates, column chromatography with Merck Silica Gel 60 (0.040–0.063 mm).…”

Section: Methodsmentioning

confidence: 99%

Nitrile Reductase from Geobacillus kaustophilus: A Potential Catalyst for a New Nitrile Biotransformation Reaction

et al. 2012

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Abstract:The cloning, expression and characterization of a nitrile reductase (NRed) from the thermophile Geobacillus kaustophilus is reported. The enzyme shows a 12-fold increase in activity in response to a temperature change from 25 8C to 658C. The substrate scope regarding its biocatalytic applicability was investigated by testing a range of common nitriles. The narrow substrate range observed for the wild-type enzyme prompted the rational design of GkNRed active site mutants based on a previously published homology model from Bacillus subtilis. The activities of the mutants and the wild-type enzyme were investigated in their structure-function relationship regarding the natural substrate 7-cyano-7-deazaguanine (preQ 0 ) as well as a range of synthesized preQ 0 -like substrate structures. A distinct dependence of the wild-type enzyme activity on specific structural modifications of the natural substrate was observed. Two non-natural nitriles derived from preQ 0 could be reduced to their corresponding amino compounds.

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Section: Methodsmentioning

confidence: 99%

Nitrile Reductase from Geobacillus kaustophilus: A Potential Catalyst for a New Nitrile Biotransformation Reaction

et al. 2012

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“…Third, the four ester groups of 6b were removed by treatment with NaOH in ethylene glycol at 170 °C. The unstable α-free derivative obtained was cyanated with chlorosulfonyl isocyanate (CSI) 22 and then transformed to BCOD-bisANBODIPY 9b with four cyano groups in 5% overall yield from 6b. Bis(dipyrromethane) 6c with two hexyloxyphenyl groups obtained from the reaction of 4c with 5 (75% yield) was converted to BCOD-bisANBODIPY 8c with four ester groups at 80% yield.…”

Section: Resultsmentioning

confidence: 99%

Benzene-fused bis(acenaphthoBODIPY)s, stable near-infrared-selective dyes

et al. 2018

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“…Chlorination of 199 with two equivalents of SO 2 Cl 2 in chloroform gives the corresponding 4,5-dichloro derivative, which may be subsequently iodinated at C3 using iodine in the presence of silver trifluoroacetate to provide methyl 4,5-dichloro-3-iodopyrrole-2-carboxylate, a useful partner for regioselective Suzuki reactions (Section 4.5.11) [307]. Pyrrole-2-carbonitrile, which is readily available by treatment of pyrrole with chlorosulfonyl isocyanate followed by warming in DMF [308], displays similar reactivity, affording 4-substituted pyrrole-2-carbonitriles [308,309]. Likewise, ethyl pyrrole-2-thiolcarboxylate (208) (readily prepared by the action of ethyl chlorothiolformate on pyrrolyl magnesium halides) also takes part in electrophilic substitution reactions, providing good yields of 2,4-disubstituted pyrroles, for example 209.…”

Section: Nitrationmentioning

confidence: 99%