Switching the chemoselectivity in the amination of 4-chloroquinazolines with aminopyrazoles.

doi:10.1021/ol902759k

Paper

Switching the chemoselectivity in the amination of 4-chloroquinazolines with aminopyrazoles.

Published Feb 5, 2010 · Zhenlu Shen, Yiming Hong, Xiaofei He

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24

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Abstract

The chemoselectivity in the amination of 4-chloroquinazolines with 3-amino-1H-pyrazoles was studied. Under the conditions of Pd(2)(dba)(3)/Xantphos/Na(2)CO(3), 4-chloroquinazolines underwent selective amination with the cyclic secondary amino group of 3-amino-1H-pyrazoles, whereas 4-chloroquinazolines were exclusively aminated with the primary amino group of 3-amino-1H-pyrazoles via S(N)Ar substitution in the presence of HCl.

Study Snapshot

Selective amination of 4-chloroquinazolines with 3-amino-1H-pyrazoles under Pd(2)(dba)(3)/Xantphos/Na(2)CO(3) conditions leads to the formation of 4-chloroquinazolines with primary amino groups in the presence of HC

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Switching the chemoselectivity in the amination of 4-chloroquinazolines with aminopyrazoles.

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References

Citations

A "Pool and Split" Approach to the Optimization of Challenging Pd-Catalyzed C-N Cross-Coupling Reactions.

This study presents a rapid screening method for Pd-catalyzed C-N cross-coupling reactions, enabling the discovery of new chemical reactions and nonobvious solutions.

Acid-Promoted Cascade Reaction of N-(4-Chloroquinolin-3-yl)carbamates with Amines: One-Pot Assembly of Imidazo[4,5-c]quinolin-2-one.

This acid-promoted cascade reaction provides rapid access to various bioactive imidazo[4,5-c]quinolin-2-one derivatives through intermolecular amination and intramolecular cyclization.

Regioselective Synthesis, NMR, and Crystallographic Analysis of N1-Substituted Pyrazoles.

Regioselective N1-alkylation, -arylation, and -heteroarylation of 3-substituted pyrazoles under basic conditions can be achieved using K2CO3-DMSO, with consistent steric effects on chemical shift.

N-(1H-Pyrazol-3-yl)quinazolin-4-amines as a novel class of casein kinase 1δ/ε inhibitors: Synthesis, biological evaluation and molecular modeling studies.

N-(1H-pyrazol-3-yl)quinazolin-4-amines show potential as CK1/ inhibitors targeting neurodegenerative disorders and cancer.

Metal Complexes of Click‐Derived Triazoles and Mesoionic Carbenes: Electron Transfer, Photochemistry, Magnetic Bistability, and Catalysis

Recent developments in metal complexes based on 1,2,3-triazoles and mesoionic carbenes have led to diverse applications, including magnetically switchable molecules, electro- and photo-active molecules, light-emitting electrochemical cells, and dye-sensitized solar cells.