92103-93-0

Upstream product

• 127-19-5 N,N-dimethyl acetamide 
• 82827-16-5 2-amino-5-bromo-N-phenylbenzamide 
• 4692-98-2 5-bromoisatoic anhydride 
• 62-53-3 aniline 
• 122-51-0 orthoformic acid triethyl ester 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 80-43-3 bis(1-methyl-1-phenylethyl)peroxide 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 123-91-1 1,4-dioxane 
• 107-21-1 ethylene glycol 
• 75-91-2 tert.-butylhydroperoxide 
• 1108665-60-6 2-amino-5-bromobenzoic acid chloride 
• 4424-17-3 2-aminobenzanilide 
• 118-48-9 isatoic anhydride 

Downstream Products

• 4546-25-2 6-bromo-2-methyl-3-phenylquinazolin-4(3H)-one 

Relevant academic research and scientific papers

Metal-free C-H methylation and acetylation of heteroarenes with PEG-400

The generation of a methyl carbon source from renewable and cheap sources is challenging. Herein, we describe a novel and an efficient route for methylation and acetylation of aza-heteroarenes using PEG-400 under O2and TsOH·H2O for the first time by tuning the reaction conditions using a different set of starting materials. The key features of the current protocol are oxidative C-O and C-C bond scission under metal-free conditions with good functional group tolerance, and a broad substrate scope. The potential applicability of the designed methodology was demonstrated for the synthesis of central nervous system (CNS) depressant and anticonvulsant drug molecules by a one-pot strategy.

Sustainable methine sources for the synthesis of heterocycles under metal- and peroxide-free conditions

Alcohols and ethers were identified as sustainable methine sources for synthesizing quinazolinone and benzimidazole derivatives using a combination of TsOH·H2O/O2 and appropriate bis-nucleophiles for the first time. Deuterium labeling studies clearly proved that the C2 hydrogen of the synthesized heterocycles came from the methine source. These unique reaction conditions were successfully applied to the synthesis of echinozolinone (2e′), 2f′ (a common precursor of rutaecarpine and (±) evodiamine), and dimedazole (6d). Notable features of this method include its low toxicity, use of commercial feedstocks as substrates, low cost, broad functional group tolerance and suitability for a wide range of bis-nucleophilic starting materials.

TBHP as Methyl Source under Metal-Free Aerobic Conditions To Synthesize Quinazolin-4(3H)-ones and Quinazolines by Oxidative Amination of C(sp3)–H Bond

tert-Butyl hydroperoxide (TBHP) served as the methyl source under metal-free aerobic conditions in the oxidative amination of the C(sp3)–H bond to synthesize quinazolin-4(3H)-ones and quinazolines from 2-aminobenzamides and 2-carbonyl-substituted anilines, respectively.

Novel Quinazolinone Inhibitors of ALK2 Flip between Alternate Binding Modes: Structure-Activity Relationship, Structural Characterization, Kinase Profiling, and Cellular Proof of Concept

Structure-activity relationship and crystallographic data revealed that quinazolinone-containing fragments flip between two distinct modes of binding to activin receptor-like kinase-2 (ALK2). We explored both binding modes to discover potent inhibitors and characterized the chemical modifications that triggered the flip in binding mode. We report kinase selectivity and demonstrate that compounds of this series modulate ALK2 in cancer cells. These inhibitors are attractive starting points for the discovery of more advanced ALK2 inhibitors.

Copper-catalyzed radical methylation/C-H amination/oxidation cascade for the synthesis of quinazolinones

A copper-catalyzed radical methylation/sp3 C-H amination/oxidation reaction for the facile synthesis of quinazolinone was developed. In this cascade reaction, dicumyl peroxide acts not only as a useful oxidant but also as an efficient methyl source. Notably, a methyl radical, generated from peroxide, was confirmed by electron paramagnetic resonance for the first time.

SUBSTITUTED BENZOFURAN COMPOUNDS AND METHODS OF USE THEREOF FOR TREATMENT OF VIRAL DISEASES

Disclosed are compounds of formula (I) that are useful as hepatitis C virus (HCV) NSSB polymerise inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NSSB polymerise activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

QUINAZOLINONE DERIVATIVES USEFUL AS FGFR KINASE MODULATORS

The invention relates to new quinazolinone derivative compounds, to pharmaceutical compositions comprising said compounds, to processes for the preparation of said compounds and to the use of said compounds in the treatment of diseases, e.g. cancer.

Metal-free oxidative synthesis of quinazolinones via dual amination of sp3 C-H bonds

A novel metal-free synthesis of quinazolinones via dual amination of sp3 C-H bonds was developed. The sp3 carbon in methylarenes or adjacent to a heteroatom in DMSO, DMF or DMA was used as the one carbon synthon. This journal is the Partner Organisations 2014.

SUBSTITUTED BENZOFURAN COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES

The present invention relates to compounds of formula I that are useful as hepatitis C virus (HCV) NS5B polymerase inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5B polymerase activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system. (I)

HETEROCYCLIC SULFONAMIDES AS RAF INHIBITORS

Compounds of Formula (I) are useful for inhibition of Raf kinases. Methods of using compounds of Formula (I), stereoisomers, tautomers and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.