141305-99-9

Upstream product

• 118-48-9 isatoic anhydride 
• 2393-23-9 4-methoxy-benzylamine 
• 221539-30-6 2-amino-N-(4-methoxybenzyl)benzamide 
• 122-51-0 orthoformic acid triethyl ester 
• 123-91-1 1,4-dioxane 
• 83-34-1 3-Methylindole 
• 107-21-1 ethylene glycol 
• 5257-06-7 N-(2-acetylphenyl)formamide 
• 1451070-63-5 C₁₇H₁₆N₂O 
• 551-93-9 2-aminoacetophenone 
• 521270-78-0 1-(2-isocyanophenyl)ethan-1-one 
• 64-18-6 formic acid 

Relevant academic research and scientific papers

Selective Oxidative Cleavage of 3-Methylindoles with Primary Amines Affording Quinazolinones

A selective functionalization of C-C-C bonds toward N-C-O bonds is realized by an n-Bu4NI-catalyzed reaction of 3-methylindoles with primary amines using TBHP as the unique oxidant. The systematic process involves oxygenation, nitrogenation, ring-opening, and recyclization, affording a broad range of quinazolinones in good to excellent yields.

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.

Glyoxylic acid in the reaction of isatoic anhydride with amines: A rapid synthesis of 3-(un)substituted quinazolin-4(3H)-ones leading to rutaecarpine and evodiamine

A dual reactant/catalyst role of glyoxylic acid in the reaction of isatoic anhydride with various amines afforded a novel, robust and rapid synthesis of 3-(un)substituted quinazolin-4(3H)-ones. This metal catalyst-free reaction proceeds via an unusual and unexpected cleavage of C-C bond. A shorter and common route to two alkaloids, that is, rutaecarpine and evodiamine is also accomplished.

Vilsmeier Reagent: An efficient reagent for the transformation of 2-aminobenzamides into quinazolin-4(3 h)-one derivatives

Clean and easy preparation of quinazolin-4(3H)-one derivatives using 2-aminobenzamides and Vilsmeier reagent is described. 2-Aminobenzamides were converted into the corresponding quinazolinones under mild and efficient conditions, in good yields without undesirable by-products.

Isocyanide cyclization reactions: 4-methylene-4H-benzo[d][1,3]oxazine, 3-benzyl-4-methylene-3,4-dihydroquinazolines and 3-(4-benzyl)-3H-quinazolin-4- ones - Experiment and theory

2-Isocyanoacetophenone (3a) was found to be an easily accessible starting material for the unexpected formation of various heterocyclic systems. Thus, a hitherto unknown rather unstable 4-methylene-4H-benzoxazine derivative 4, which could be characterized by NMR spectroscopy, was formed in situ by the reaction of 3a in the presence of weak acids. In the presence of benzylamines, a new class of 3,4-dihydroquinazoline derivatives 6 and their oxidation products, quinazolin-4-ones 9, were obtained. The starting materials and products were completely characterized by spectroscopic and X-ray analysis. The scope and limitations of these cyclization reactions were investigated under various reaction conditions. High-level quantum chemical calculations were carried out to elucidate the mechanisms leading to scaffolds 4 and 6. The calculations suggest that the formation of 4 and 6 involves the generation of an unusual six-membered N-heterocyclic carbene or its C-protonated form as a reaction intermediate, followed by tautomerisation. This mechanism might also be applicable to other isocyanide cyclization reactions. Copyright

Green synthesis of quinazolinone derivatives catalyzed by iodine in ionic liquid

A series of quinazolinone derivatives were synthesized by the reaction of 2-aminobenzamides and triethyl orthoformate or triphosgene in ionic liquid of [BMIm]BF4 at 80 °C catalyzed by iodine in good yields. Compared to other methods, this new procedure has the advantages of mild reaction conditions, good yields, operational simplicity, and environmentally friendly procedure. Copyright Taylor & Francis Group, LLC.

Synthesis and in vitro study of platelet antiaggregant activity of some 4-quinazolinone derivatives

Some new 4-quinazolinones were prepared. Their antiplatelet activity was evaluated in vitro with respect to aggregation induced by ADP, collagen, arachidonic acid and the platelet serotonin release reaction. Most molecules showed an inhibiting power similar to that of acetylsalicylic acid under the same conditions, and even greater when aggregation was induced by ADP. Reduction of the 4-quinazolinone derivatives to their 1,2,3,4-tetrahydroquinazoline homologues produced an increase in platelet inhibitory action except when ADP is the inductor.