A rapid method toward the synthesis of new substituted tetrahydro α-carbolines and α-carbolines

Chavan, Neelam L.; Nayak, Sandip K.; Kusurkar, Radhika S.

doi:10.1016/j.tet.2010.01.042

Cited by 20 publications

(7 citation statements)

References 16 publications

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“…Reaction of compound 15 with phenylboronic acid led only to recovery of unreacted starting material. Therefore, the pyrrole nitrogen of the 7-azaindole scaffold was protected as a tosyl group, affording compound 16 . A regioselective Suzuki coupling reaction using phenylboronic acid furnished the 3-phenyl-pyrrolo[2,3- b ]pyridine analogue 17 .…”

Section: Resultsmentioning

confidence: 99%

“…Formylation of compound 4 by a Duff reaction 25 yielded 3-formyl-5-bromo-azaindole 9 (Scheme 2). The pyrrole nitrogen was protected 26 using NaH and tosylchloride yielding compound 10. Suzuki coupling reaction with 3,4-dimethoxyphenylboronic acid furnished compound 11.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Reaction of compound 15 with phenylboronic acid led only to recovery of unreacted starting material. Therefore, the pyrrole nitrogen of the 7-azaindole scaffold was protected as a tosyl group, 26 affording compound 16. A regioselective Suzuki coupling Sonogashira reaction of compound 15 with a number of (hetero)arylacetylenes yielded regioselectively compounds 20a−f in yields varying from 20 to 70% (Scheme 4).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Purification by silica gel flash chromatography using a mixture of DCM and ethyl acetate (in a ratio of 9:1) as the mobile phase yielded the title compound as a yellow solid (90 mg, 83%). 1 (26). The title compound was synthesized according to the general procedure described for the synthesis of compounds 8a−h, starting from 5-(3,4-dimethoxyphenyl)-1-methyl-3-nitro-1H-pyrrolo[2,3-b]pyridine 24 (90 mg, 0.287 mmol).…”

Section: Journal Of Medicinal Chemistrymentioning

confidence: 99%

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Synthesis and Structure–Activity Relationships of 3,5-Disubstituted-pyrrolo[2,3-b]pyridines as Inhibitors of Adaptor-Associated Kinase 1 with Antiviral Activity

Verdonck

Sorrell

et al. 2019

J. Med. Chem.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Reaction of compound 15 with phenylboronic acid led only to recovery of unreacted starting material. Therefore, the pyrrole nitrogen of the 7-azaindole scaffold was protected as a tosyl group, 26 affording compound 16. A regioselective Suzuki coupling Sonogashira reaction of compound 15 with a number of (hetero)arylacetylenes yielded regioselectively compounds 20a−f in yields varying from 20 to 70% (Scheme 4).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Journal Of Medicinal Chemistrymentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and Structure–Activity Relationships of 3,5-Disubstituted-pyrrolo[2,3-b]pyridines as Inhibitors of Adaptor-Associated Kinase 1 with Antiviral Activity

Verdonck

Sorrell

et al. 2019

J. Med. Chem.

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“…Electrocyclic ring closures forming the pyridine ring from 2-aminoindole-derived intermediates are also known [62–64]. In addition, cycloadditions of 3-vinyl-7-azaindole have also been used to close the pyridine ring [65], as have intramolecular dipolar cycloadditions of 2-azidoindole derivatives [66], and intramolecular cycloadditions of carbodiimides [67–68]. …”

Section: Introductionmentioning

confidence: 99%

An intramolecular inverse electron demand Diels–Alder approach to annulated α-carbolines

Feng²,

Woo³

et al. 2012

Beilstein J. Org. Chem.

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SummaryIntramolecular inverse electron demand cycloadditions of isatin-derived 1,2,4-triazines with acetylenic dienophiles tethered by amidations or transesterifications proceed in excellent yields to produce lactam- or lactone-fused α-carbolines. Beginning with various isatins and alkynyl dienophiles, a pilot-scale library of eighty-eight α-carbolines was prepared by using this robust methodology for biological evaluation.

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Palladium‐Catalyzed Decarboxylative Suzuki and Heck Couplings of Azaindole‐2‐carboxylic Acids: Synthesis of 2‐Aryl/Alkenyl‐1‐phenylsulfonyl‐1 H‐pyrrolo‐[2,3 b]pyridines

et al. 2013

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A series of 2‐aryl‐1‐(phenylsulfonyl)‐1H‐pyrrolo[2,3‐b]pyridines 3 were obtained by a palladium‐catalyzed decarboxylative Suzuki coupling of azaindole‐2‐carboxylic acid derivative 1. The synthesis of alkenyl‐1‐(phenylsulfonyl)‐1H‐pyrrolo[2,3‐b]pyridines 9 by a related Heck coupling is also described. Protodecarboxylation operates in the case of azaindole‐3‐carboxylic acids under the reaction conditions.

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A rapid method toward the synthesis of new substituted tetrahydro α-carbolines and α-carbolines

Cited by 20 publications

References 16 publications

Synthesis and Structure–Activity Relationships of 3,5-Disubstituted-pyrrolo[2,3-b]pyridines as Inhibitors of Adaptor-Associated Kinase 1 with Antiviral Activity

Synthesis and Structure–Activity Relationships of 3,5-Disubstituted-pyrrolo[2,3-b]pyridines as Inhibitors of Adaptor-Associated Kinase 1 with Antiviral Activity

An intramolecular inverse electron demand Diels–Alder approach to annulated α-carbolines

Palladium‐Catalyzed Decarboxylative Suzuki and Heck Couplings of Azaindole‐2‐carboxylic Acids: Synthesis of 2‐Aryl/Alkenyl‐1‐phenylsulfonyl‐1 H‐pyrrolo‐[2,3 b]pyridines

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