Synthesis of 4- and 6-Azaindoles via the Fischer Reaction

Jeanty, Matthieu; Blu, Jérôme; Suzenet, Franck; Guillaumet, Gérald

doi:10.1021/ol902139r

Cited by 53 publications

(36 citation statements)

References 56 publications

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“…This strategy for the synthesis of azaindoles was previously evaluated with cyclic ketones 13. We were interested in using cyclic 1,3‐diones, as this could give an efficient synthesis of azacarbazolone derivatives.…”

Section: Resultsmentioning

confidence: 99%

“…To further extend the potential of the aza‐Fischer reaction, we replaced the methoxy or methylsulfonyl group13 on the pyridine ring by a halogen, to allow further metal‐catalyzed cross‐coupling reactions, aromatic nucleophilic substitutions, metalation reactions,16 etc. on the desired azaindole products.…”

Section: Resultsmentioning

confidence: 99%

“…We then focused our attention on 2‐hydrazino‐6‐methoxypyridine ( 22 ), which was not reactive under conventional heating 13. Starting from 2‐bromo‐6‐methoxypyridine ( 21 ) and an excess of hydrazine monohydrate, and heating at 160 °C for 20 min under microwave irradiation, we obtained the expected pyridylhydrazine (i.e., 22 50 %; Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…In the context of the synthesis of azaindoles with potential biological activity,12 we described, in a previous letter, the efficient synthesis of 4‐aza‐ and 6‐azaindoles bearing an electron‐donating group using the Fischer reaction (Scheme ) 13. This sequence has since been extended to the formation of alternative hydrazine intermediates and to other pyrrole‐fused heterocycles 14.…”

Section: Introductionmentioning

confidence: 99%

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Selective Hydrogenation of Phenol to Cyclohexanone in Water over Pd@N‐Doped Carbon Derived from Ionic‐Liquid Precursors

Wang

2014

ChemCatChem

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In this report, a kind of mesoporous N‐doped carbon (CN‐x) derived from N‐containing ionic‐liquid (IL) precursors were synthesized, and Pd@CN‐x prepared by a simple ultrasound‐assisted method showed higher catalytic activity for the selective hydrogenation of phenol and its derivatives under mild reaction conditions in water than commercial Pd@C and other common Pd heterogeneous catalysts. The catalytic activities of Pd@CN‐x derived from different ILs were different, and further study into the influencing factors, including physical properties, N species of CN‐x, and Pd status of Pd@CN‐x, were performed.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Selective Hydrogenation of Phenol to Cyclohexanone in Water over Pd@N‐Doped Carbon Derived from Ionic‐Liquid Precursors

Wang

2014

ChemCatChem

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“…16 Using this method, Suzenet and co-workers obtained recently a convenient access to 2,3-bisalkyles-4-azaindoles. 17 However, they never tried to incorporate simultaneously two (het)aryl moieties in both C-2 and C-3 positions.…”

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confidence: 99%

Synthesis and biological evaluation of 2,3-bis(het)aryl-4-azaindole derivatives as protein kinase inhibitors

Pin¹,

Buron²,

Saab³

et al. 2011

Med. Chem. Commun.

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International audienceThe synthesis of several novel 4-azaindoles was carried out by novel Fischer reaction which offers as a main advantage, the synthesis of the bisfunctionalized 4-azaindolic building block in one step. The final compounds were evaluated on a panel of 5 kinases in order to evaluate their selectivity and on 7 cancer cell lines to determine their cytotoxic effects. RAF-1 and DYRK1A inhibitions were found, docking studies explain fully the results

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The Xanthate Route to Indolines, Indoles, and their Aza Congeners

Zard

2020

Chemistry A European J

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Convergentr outes to av ariety of indolines, indoles, oxindoles, and their aza analogues involving radical additions of xanthates are described. Three approaches are summarized. The first is the least general and relies on the generation of aryl or heteroaryl radicals startingf rom diazonium salts. The second involves radical addition to N-allylanilines followed by ring-closure onto the aromatic core. A large varietyo fi ndolines and azaindolines can thus be obtained and, in many cases, converted into the corresponding indoles and azaindoles by variousm ethods. Thes ynthesiso f novel fluoroazaindolines and fluoroazaindoles by ar are homolytic ipso-substitution of fluorine atoms is particularly noteworthy.T he last approachh inges on the direct modification of indoles by radical addition to the pyrrole subunit of the indolen ucleus. Application of this methodology to the total synthesis of melatonin andt he alkaloids mersicarpine, caulerpine, and the pentacyclic skeleton of tronocarpine is briefly discussed. Mosto ft he compounds described herein would be difficult to obtain by more traditional routes.

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Synthesis of 4- and 6-Azaindoles via the Fischer Reaction

Cited by 53 publications

References 56 publications

Selective Hydrogenation of Phenol to Cyclohexanone in Water over Pd@N‐Doped Carbon Derived from Ionic‐Liquid Precursors

Selective Hydrogenation of Phenol to Cyclohexanone in Water over Pd@N‐Doped Carbon Derived from Ionic‐Liquid Precursors

Synthesis and biological evaluation of 2,3-bis(het)aryl-4-azaindole derivatives as protein kinase inhibitors

The Xanthate Route to Indolines, Indoles, and their Aza Congeners

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