5605-26-5

Upstream product

• 43083-12-1 1,1,1-trimethoxybutane 
• 4424-17-3 2-aminobenzanilide 
• 118-48-9 isatoic anhydride 
• 62-53-3 aniline 
• 33913-15-4 N-o-tolylbutyramide 
• 6833-13-2 2-chlorobenzanilide 
• 109-73-9 N-butylamine 
• 123-72-8 butyraldehyde 
• 118-92-3 anthranilic acid 
• 6328-94-5 2-[(1-oxobutyl)amino]benzoic acid 

Relevant academic research and scientific papers

Method for synthesizing quinazolinone compound under photocatalysis condition

The invention belongs to the technical field of compound preparation. The invention discloses a method for synthesizing a quinazolinone compound under a photocatalysis condition. The method comprisesthe following step: by taking a compound shown as a formula I and a compound shown as a formula II as raw materials and copper salt or nickel salt or iron salt as a catalyst, performing a cyclizationreaction in a nitrogen atmosphere, an illumination condition, an oxygen atmosphere and an illumination condition in sequence under the action of an alkali and a solvent to synthesize the quinazolinonecompound shown as a formula III. According to the method, under the illumination condition, o-halogen benzamide can not only react with fatty amine, but also react with benzylamine to obtain the quinazolinone compound.

One-Pot Synthesis of Quinazolin-4(3H)-ones through Anodic Oxidation and the Related Mechanistic Studies

A metal-free and oxidant-free method for the one-pot preparation of quinazolin-4(3H)-ones enabled by electrochemical oxidation is described. Together with 2-aminobenzamides, a variety of aldehydes were successfully applied to an acid-catalyzed annulation and direct anodic oxidation cascade, affording structurally diverse quinazoline-4(3H)-ones in good to excellent yields. Additionally, certain alcohols can be directly applied instead of the corresponding aldehydes to achieve the same final products with the assistance of an electrolysis mediator (TEMPO). The reaction mechanism was carefully examined and the results strongly suggest that the direct and indirect oxidation go through different pathways. As an efficient and environmentally friendly access to a broad range of quinazolin-4(3H)-ones, the synthetic utility of this method was demonstrated by gram-scale operation, as well as the preparation of bioactive mackinazolinone and truncated erlotinib. (Figure presented.).

Copper-Catalyzed Tandem Reaction of 2-Aminobenzamides with Tertiary Amines for the Synthesis of Quinazolinone Derivatives

We developed a copper-catalyzed tandem reaction of 2-aminobenzamides with tertiary amines for the formation of quinazolinone derivatives. The strategy includes two steps (cyclization and coupling) performed in one pot. A number of substrates reacted well under standard conditions to give the corresponding quinazolinone derivatives in moderate to good yields.

Metal-free one-pot synthesis of 1,3-diazaheterocyclic compounds via I2-mediated oxidative C-N bond formation

A one-pot I2-mediated annulation reaction of substrates containing diamino groups and aldehydes has been developed via oxidative C-N bond formation. This general and environmentally benign synthetic approach provides facile access to a variety of 1,3-diazaheterocyclic compounds, including quinazolinones, benzimidazoles, and cyclic amidines.

KAl(SO4)2·12H2O (Alum) catalyzed one-pot three-component synthesis of 2-alkyl and 2-aryl-4(3H)-quinazolinone under microwave irradiation and solvent free conditions

Twenty 2,3-disubstituted-4(3H)-quinazolinones were synthesed by one-pot three-component method with isatoic anhydride, orthoesters and amines as raw materials in the presence of KAl(SO4)2·12H 2O (Alum) under microwave irradiation and solvent-free conditions. 6-Bromo-2-propyl-3-p-tolylquinazolin-4(3H)-one (4m), 6-bromo-2-methyl-3- phenethylquinazolin-4(3H)-one (4n) and 6-bromo-2-ethyl-3-phenethylquinazolin- 4(3H)-one (4o) were characterized by IR, 1H NMR, 13C NMR and elemental analysis. Twenty 2,3-disubstituted-4(3H)-quinazolinones were synthesed by one-pot three-component method with isatoic anhydride, orthoesters and amines as raw materi-als in the presence of KAl(SO4) 2·12H2O (Alum) under microwave irradiation and solvent-free conditions. 6-Bromo-2-propyl-3-p-tolylquinazolin-4(3H)-one (4m), 6-bromo-2-methyl-3-phenethylquinazolin-4(3H)-one (4n) and 6-bromo-2-ethyl-3- phenethylquina-zolin-4(3H)-one (4o) were characterized by IR, 1H NMR, 13C NMR and elemental analysis. Copyright

Synthesis and structure-activity relationships of vasicine analogues as bronchodilatory agents

The series of vasicine (1) analogues, an alkaloid from Adhatoda vasica Nees., were synthesized with changes in A, B or C rings. Compounds 3-19 were evaluated for in vitro bronchodilatory activity using isolated guinea pig tracheal chain. Compounds 3-8 were also synthesized in good yields using microwave-mediated synthesis under solvent free conditions. Compounds 5 and 8 with seven-member C ring were more active than etofylline and caused 100% relaxation of both the histamine and acetylcholine pre-contracted guinea pig tracheal chain. The structure-activity relationship studies showed that the quinazoline and oxo functionalities were essential for activity. The compounds without C ring and instead having aliphatic and phenyl substitutions in B ring showed relaxation against histamine pre-contracted tracheal chain only, 2-methyl substituted analogues, 12 and 13, being most active with 100% relaxation effect. Birkhaeuser Boston 2006.

One-pot synthesis of mono- and disubstituted (3H)-quinazolin-4-ones in dry media under microwave irradiation

AlCl3/ZnCl2 mixture supported on silica gel is an efficient medium for one-pot synthesis of (3H)-quinazolin-4-ones in the absence of solvent under microwave irradiation or classical heating. The reaction of orthoesters with 2-aminobenzamides ends up with the formation of monosubstituted (3H)-quinazolin-4-ones. One-pot synthesis of disubstituted (3H)-quinazolin-4- ones is also achieved by the reaction of isatoic anhydride with primary amines and orthoesters.

Montmorillonite K-10 catalysed solvent-free synthesis of 2,3-disubstituted-4(3H)quinazolinones under microwave irradiation

An efficient and rapid synthesis of 2,3-disubstituted-4(3H)quinazolinones by condensation of 2-aminobenzamide (substituted anthraniamides) with orthoesters in the presence of K-10 clay under solvent free conditions using microwave irradiation or classical heating is described.