141305-99-9

Basic information

• Product Name: 4(3H)-Quinazolinone, 3-[(4-methoxyphenyl)methyl]-
• CAS NO: 141305-99-9
• Molecular Formula: C16H14N2O2
• Molecular Weight: 266.299
• Mol File: 141305-99-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 4(3H)-Quinazolinone, 3-[(4-methoxyphenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 4(3H)-Quinazolinone, 3-[(4-methoxyphenyl)methyl]-(141305-99-9)
• EPA Substance Registry System: 4(3H)-Quinazolinone, 3-[(4-methoxyphenyl)methyl]-(141305-99-9)

Safety Data

• Hazardous Substances Data: 141305-99-9(Hazardous Substances Data)

Upstream product

• 83-34-1 3-Methylindole 
• 2393-23-9 4-methoxy-benzylamine 
• 118-48-9 isatoic anhydride 
• 123-91-1 1,4-dioxane 
• 221539-30-6 2-amino-N-(4-methoxybenzyl)benzamide 
• 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 
• 122-51-0 orthoformic acid triethyl ester 
• 64-18-6 formic acid 

Relevant articles and documents

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.

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.

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