Chemoselective N‐Acylation of Indoles and Oxazolidinones with Carbonylazoles

Heller, Stephen T.; Schultz, Erica E.; Sarpong, Richmond

doi:10.1002/anie.201203976

Cited by 58 publications

(53 citation statements)

References 32 publications

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“…The carbonylimidazole derivatives are a class of highly acylation reagents, particularly in the preparation of esters and amides [39][40][41][42]. In several cases, they have shown superior selectivity for selective acylation reactions [43][44][45] and N-acetylation of oxindoles and indoles (Scheme 2) [46]. Inspired by these works, we decided to explore the possibility of replacing the acyl halide, which is toxic and unstable, with 1-benzoylimidazole as the benzoylation reagent with 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU) as the catalyst.…”

Section: Resultsmentioning

confidence: 99%

Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase

Hou

Ren

et al. 2016

Molecules

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Abstract:A novel metal-free organobase-catalyzed regioselective benzoylation of diols and carbohydrates has been developed. Treatment of diol and carbohydrate substrates with 1.1 equiv. of 1-benzoylimidazole and 0.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in MeCN under mild conditions resulted in highly regioselective benzoylation for the primary hydroxyl group. Importantly, compared to most commonly used protecting bulky groups for primary hydroxyl groups, the benzoyl protective group offers a new protection strategy.

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Section: Resultsmentioning

confidence: 99%

Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase

Hou

Ren

et al. 2016

Molecules

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“…The tertiary nitrogen of these compounds reacted with CO 2 to form the carbamate species, which resulted in the activation of CO 2 , facilitating the reactions [29][30][31][32][33][34][35][36]. Moreover, from an organic synthesis point of view, base-promoted reactions also provide a very important complementary methodology for transition-metal catalyst systems [37][38][39][40]. In this work, a series of organic bases, including 1,5,7- (Figure 1), was investigated for the cyclocarbonylation of 2-aminothiophenols with CO 2 .…”

Section: Introductionmentioning

confidence: 99%

Organic Base-Catalyzed C–S Bond Construction from CO2: A New Route for the Synthesis of Benzothiazolones

Gao

Deng

et al. 2018

Catalysts

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Abstract:The synthesis of organosulfur compounds via the construction of C−S bonds using CO 2 as a C1 resource is very interesting. Herein, a novel method of synthesizing benzothiazolones via the cyclocarbonylation of 2-aminothiophenols with CO 2 was developed. A series of organic bases was investigated for the catalysis of cyclocarbonylation, and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) displayed the best catalytic activity. Then, various reaction parameters such as CO 2 pressure, temperature, amount of catalyst, and reaction time for the catalytic performance were studied. Finally, a series of benzothiazolones was synthesized under the optimal reaction conditions, and a possible catalytic mechanism was also proposed.

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“…Imidazole carbamates and ureas have been successfully applied in the conversion of aliphatic and aromatic carboxylic acids into esters and amides in 70-93% yields [14]. In this endeavor, Sarpong et al have reported the selective acetylation of indoles and oxazolidinones by using several reactive N-acyl imidazoles and/or carbamates; the reaction shows a high selectivity at the nitrogen atom of the non-nucleophilic azacycles, even in the presence of other strong nucleophiles, such as amines or hydroxyl groups [15]. The reaction, conducted at room temperature in acetonitrile for about 24 h, a General reaction conditions: 1 (0.8 mmol.…”

Section: Introductionmentioning

confidence: 99%

Selective Acetylation of Small Biomolecules and Their Derivatives Catalyzed by Er(OTf)3

et al. 2017

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It is of great significance to develop sustainable processes of catalytic reaction. We report a selective procedure for the synthesis of acetylated bioactive compounds in water. The use of 1-acetylimidazole combined with Er(OTf) 3 as a Lewis acid catalyst gives high regioselectivity and good yields for the acetylation of primary hydroxyl groups, as well as amino groups. The protection is achieved in short reaction times under microwave irradiation, and is successful even in the case of base-sensitive substrates.

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Chemoselective N‐Acylation of Indoles and Oxazolidinones with Carbonylazoles

Cited by 58 publications

References 32 publications

Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase

Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase

Organic Base-Catalyzed C–S Bond Construction from CO2: A New Route for the Synthesis of Benzothiazolones

Selective Acetylation of Small Biomolecules and Their Derivatives Catalyzed by Er(OTf)3

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