A convenient approach to 3-trifluoromethyl-6-azaindoles

Ivonin, S. P.; Yurchenko, A. A.; Voloshchuk, Volodymyr V.; Yurchenko, S. A.; Русанов, Эдуард Б.; Пироженко, В. В.; Volochnyuk, Dmitriy M.; Kostyuk, Alexander

doi:10.1016/j.jfluchem.2020.109509

Cited by 8 publications

(14 citation statements)

References 13 publications

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“…Crystals suitable for investigation were obtained after crystallization of crude product 5c from MTBE. In this case, the structure turned out to be a TFA salt of the corresponding hydrate (analogous to CCDC 1976873) 8 Scheme 1 Results for the reaction employing the model set of aminopyridines.…”

Section: Resultsmentioning

confidence: 99%

“…Combination of all obtained experimental results does not agree with the cyclization mechanism we previously proposed and implies that compounds of type 13 are intermediates in the cyclization. 8 In this regard, we checked the possibility of trifluoroacetylation of compound 13 under cyclization conditions and found that compound 13 is unreactive towards TFAA. Therefore, the installation of the COCF 3 group occurs in earlier steps before cyclization.…”

Section: Resultsmentioning

confidence: 99%

“…First, we modified a procedure of pyrrole ring fusion using an earlier published method as the starting point. 8 Based on parent 3-amino-4-methylpyridine ( 1a ), the procedure was updated to a one-pot protocol, avoiding the isolation of N -trifluoroacylated derivative 6a . A 0.2 M solution of the starting aminopyridine 1a in dry pyridine was treated with 3.3 equiv.…”

Section: Resultsmentioning

confidence: 99%

“…Thus, despite the number of known approaches to such an azaindole core, new effective routes that lead to an unknown architecture of substituents and expand the scope and overcome the limitations of available methodologies will still be valuable. 10,11 Recently, our group has elaborated a scalable and efficient synthesis of 2-trifluoromethyl-6-azaindole from 3-trifluoroacetylamino-4-methylpyridine, 8 which has been recognized by the scientific community. 12 The method was based on formal [4 + 1]-cyclization, where TFAA plays the role of a C1-bielectrophile and additionally acts as a trifluoroacetylating agent (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, our group has elaborated a scalable and efficient synthesis of 2-trifluoromethyl-6-azaindole from 3-trifluoroacetylamino-4-methylpyridine, 8 which has been recognized by the scientific community. 12 The method was based on formal [4 + 1]-cyclization, where TFAA plays the role of a C1-bielectrophile and additionally acts as a trifluoroacetylating agent (Fig.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 6-azaindoles via formal electrophilic [4 + 1]-cyclization of 3-amino-4-methyl pyridines: new frontiers of diversity

Ivonin,

Voloshchuk,

Rusanov

et al. 2024

Org. Chem. Front.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of 6-azaindoles via formal electrophilic [4 + 1]-cyclization of 3-amino-4-methyl pyridines: new frontiers of diversity

Ivonin,

Voloshchuk,

Rusanov

et al. 2024

Org. Chem. Front.

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Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates

Barata‐Vallejo,

Yerien,

Zottola

et al. 2024

Eur J Org Chem

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The direct addition of perfluoroacyl (‐CORF) groups to organic frameworks has seen a resurgence in interest due to the benefits of these groups in late‐stage modification of pro‐drugs and biologically active compounds, helping to identify new active leads. The presence of ‐CORF groups positively impacts the structure‐activity relationships of these compounds. In that sense, both polar methods and radical catalytic protocols have been developed for the direct syntheses of trifluoromethyl and perfluoroalkyl ketones. In particular, methodologies to tame the unstable trifluoroacyl radical, which could be a key intermediate in the late‐stage syntheses of trifluoroacyl‐substituted compounds, has allowed much progress in this area. In the next sections, the direct incorporation of perfluoroacyl groups into (hetero)aromatic compounds, ‐CORF substitutions at Csp3‐H, alkyl halides, alkenes, amides, and N‐atoms will be discussed in detail, suggesting the future directions and perspectives in the field. These known reactions are summarized in Table 1.

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