Intramolecular C—H Amination Reactions: Exploitation of the Rh<sub>2</sub>(II)‐Catalyzed Decomposition of Azidoacrylates.

Stokes, Benjamin J.; Dong, Huijun; Leslie, Brooke E.; Pumphrey, Ashley L.; Driver, Tom G.

doi:10.1002/chin.200742039

Cited by 5 publications

(5 citation statements)

References 7 publications

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“…86 Condensation with piperonal provided the corresponding vinyl azide 9 as reported. 87 Following the reaction with triphenyl- products (L59, L62, 14) were obtained by alkylation of the corresponding (Z)-thiohydantoi ̈n with the appropriate halogenated reagent. N-Substituted analogues were prepared by displacement of the SEt group under microwave irradiation conditions with a large variety of primary and secondary aromatic amines.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Structure–Activity Relationship in the Leucettine Family of Kinase Inhibitors

et al. 2021

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The protein kinase DYRK1A is involved in Alzheimer’s disease, Down syndrome, diabetes, viral infections, and leukemia. Leucettines, a family of 2-aminoimidazolin-4-ones derived from the marine sponge alkaloid Leucettamine B, have been developed as pharmacological inhibitors of DYRKs (dual specificity, tyrosine phosphorylation regulated kinases) and CLKs (cdc2-like kinases). We report here on the synthesis and structure–activity relationship (SAR) of 68 Leucettines. Leucettines were tested on 11 purified kinases and in 5 cellular assays: (1) CLK1 pre-mRNA splicing, (2) Threonine-212-Tau phosphorylation, (3) glutamate-induced cell death, (4) autophagy and (5) antagonism of ligand-activated cannabinoid receptor CB1. The Leucettine SAR observed for DYRK1A is essentially identical for CLK1, CLK4, DYRK1B, and DYRK2. DYRK3 and CLK3 are less sensitive to Leucettines. In contrast, the cellular SAR highlights correlations between inhibition of specific kinase targets and some but not all cellular effects. Leucettines deserve further development as potential therapeutics against various diseases on the basis of their molecular targets and cellular effects.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Structure–Activity Relationship in the Leucettine Family of Kinase Inhibitors

et al. 2021

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“…Depending on the application, the ester group at the 2-position can be later modified. 9 As reported by Driver and co-workers, 10 the thermolysis of the azide and C−H amination can be performed under milder conditions in the presence of rhodium catalyst.…”

Section: ■ Synthesismentioning

confidence: 96%

Multifunctional Heteropentalenes: From Synthesis to Optoelectronic Applications

Stecko

Gryko

2022

JACS Au

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In the broad family of heteropentalenes, the combination of two five-membered heterocyclic rings fused in the [3,2- b ] mode has attracted the most significant attention. The relatively straightforward access to these structures, being a consequence of the advances in the last two decades, combined with their physicochemical properties which match the requirements associated with many applications has led to an explosion of applied research. In this Perspective, we will discuss the recent progress of heteropentalenes’ usefulness as an active element of organic light-emitting diodes and organic field-effect transistors. Among the myriad of possible combinations for the different heteroatoms, thieno[3,2- b ]thiophenes and 1,4-dihydropyrrolo[3,2- b ]pyrroles are subject to the most intense studies. Together they comprise a potent optoelectronics tool resulting from the combination of appreciable photophysical properties, chemical reactivity, and straightforward synthesis.

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“…[54][55][56] In addition, Driver reported that rhodium(II) carboxylates such as the electron-poor Rh2(O2CC3F7)4 or the electron-rich Rh2(O2CC7H15)4 can catalyze the intramolecular formation of C-N bonds from vinyl or aryl azides to provide indole and pyrrole derivatives. 57 Based on our own experience, the Du Bois catalyst bis[rhodium (α,α,α',α'-tetramethyl-1,3benzenedipropionic acid)] Rh2(esp)2, has proven to be exceptionally effective for nitrene insertion of aromatic C-H bonds. [58][59] Thus, we decided to investigate this Rh2(esp)2 catalyst nitrene aromatic insertion of 2-trichloromethyl-4-azido-pyrimidines 2.…”

Section: Scheme 5 Synthesis Of 2-trichloromethylpyrimido[45-b]indole ...mentioning

confidence: 99%

Nitrene Cyclization of 2-(Trichloromethyl)-5-phenylpyrimidines: Application to the Synthesis of 2-(Trichloromethyl)pyrimido[4,5-b]indoles and Related Heterocycles

Romero-Ortega,

Vargas-Cruz,

Peralta-Chávez

et al. 2023

Synthesis

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An aromatic C–H nitrene insertion of 2-trichloromethylpyrimidines bearing a phenyl substituent in C-5 position is described. Treatment of 2-trichloromethyl-4-chloro-5-phenylpyrimidines with sodium azide in DMF or the reflux of 2-trichloromethyl-4-azido-5-phenylpyrimidines in toluene provided 2-trichloromethylpyrimido[4,5-b]indole derivatives in moderate yields. Excellent yields of this heterocyclic systems were obtained through of the aromatic C–H insertion with Du Bois catalyst. This is an attractive approach for synthesizing pyrimido[4,5-b]indoles with a trichloromethyl substituent in the pyrimidine moiety.

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Intramolecular C—H Amination Reactions: Exploitation of the Rh₂(II)‐Catalyzed Decomposition of Azidoacrylates.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 5 publications

References 7 publications

Structure–Activity Relationship in the Leucettine Family of Kinase Inhibitors

Structure–Activity Relationship in the Leucettine Family of Kinase Inhibitors

Multifunctional Heteropentalenes: From Synthesis to Optoelectronic Applications

Nitrene Cyclization of 2-(Trichloromethyl)-5-phenylpyrimidines: Application to the Synthesis of 2-(Trichloromethyl)pyrimido[4,5-b]indoles and Related Heterocycles

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Intramolecular C—H Amination Reactions: Exploitation of the Rh2(II)‐Catalyzed Decomposition of Azidoacrylates.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 5 publications

References 7 publications

Structure–Activity Relationship in the Leucettine Family of Kinase Inhibitors

Structure–Activity Relationship in the Leucettine Family of Kinase Inhibitors

Multifunctional Heteropentalenes: From Synthesis to Optoelectronic Applications

Nitrene Cyclization of 2-(Trichloromethyl)-5-phenylpyrimidines: Application to the Synthesis of 2-(Trichloromethyl)pyrimido[4,5-b]indoles and Related Heterocycles

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Intramolecular C—H Amination Reactions: Exploitation of the Rh₂(II)‐Catalyzed Decomposition of Azidoacrylates.