71047-77-3

Upstream product

• 284465-78-7 N-(4-chloro-benzoyl)-anthranilic acid anilide 
• 37613-10-8 4-chloro-N-phenyl-benzimidoyl chloride 
• 134-20-3 2-carbomethoxyaniline 
• 18600-52-7 2-(4-chlorophenyl)-4H-benzo[d][1,3]oxazin-4-one 
• 201230-82-2 carbon monoxide 
• 615-43-0 2-iodophenylamine 
• 118-48-9 isatoic anhydride 
• 104-88-1 4-chlorobenzaldehyde 
• 62-53-3 aniline 
• 122-01-0 4-chloro-benzoyl chloride 
• 118-92-3 anthranilic acid 
• 5344-90-1 2-Aminobenzyl alcohol 
• 66343-79-1 4‐chlorophenyl‐[²H]‐methanol 
• 74083-55-9 4,5-diphenyl-3-(4-chlorophenyl)-4,5-dihydro-1,2,4-oxadiazole 

Relevant academic research and scientific papers

Complementary Reactivity in Selective Radical Processes: Electrochemistry of Oxadiazolines to Quinazolinones

Electrochemistry has recently emerged as a sustainable approach for efficiently generating radical intermediates utilizing eco-friendly electric energy. An electrochemical process was developed to transform 1,2,4-oxadiazolines under mild conditions. The electrochemical N-O bond cleavage at a controlled oxidation potential led to the selective synthesis of quinazolinone derivatives that could not be obtained by photocatalytic radical processes, indicating complementary reactivities in radical processes. The electrochemical reaction pathways were fully revealed by density functional theory-based investigations.

Palladium-Catalyzed Oxidative Three-Component Coupling of Anthranilamides with Isocyanides and Arylboronic Acids: Access to 2,3-Disubstituted Quinazolinones

A novel palladium-catalyzed oxidative three-component coupling of easily accessible N-substituted anthranilamides with isocyanides and arylboronic acids is achieved. This protocol offers an alternative approach toward 2,3-disubstituted quinazolinones with a wide substrate scope and good functional group tolerance.

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.).

T3P catalyzed one pot three-component synthesis of 2,3-disubstituted 3H-quinazolin-4-ones

Abstract An efficient methodology for the synthesis of 2,3-disubstituted 3H-quinazolin-4-ones is described via one-pot three component reaction from anthranilic acid using T3P as catalyst. Mild reaction conditions, short reaction time, broad functional group tolerance, easy isolation of products and good yields are main advantages of this protocol.

Efficient and practical one-pot route to synthesise quinazolin4(3H)-ones using trifluoromethanesulfonic anhydride and 2-chloropyridine

An effective, novel and rapid one-pot three-component route to quinazolin-4(3H)-ones from commercially available starting materials is described. Isatoic anhydride reacts with acyl chlorides and different amines using a combination of trifluoromethanesulf

Development of a New Synthetic Method for Quinazolinones via Aerobic Oxidation in dimethylsulfoxide

The present invention relates to a method for preparing quinazoline derivatives by aerobic oxidation using oxygen as an oxidizing agent in dimethylsulfoxide (DMSO) solvent wherein metal and base are excluded. The method for preparing quinazoline derivatives according to the present invention does not require any metal catalyst such as palladium or iridium, and thus does not cause toxicity problem of residual metal; and does not require demanding processes such as strong acid, or base conditions, low temperature reactions, or reactions of anhydrous conditions and thus, it is possible to simply and economically prepare quinazoline derivatives by reacting anthranilamide derivatives and an aldehyde source.

Synthesis of quinazolinones from anthranilamides and aldehydes via metal-free aerobic oxidation in DMSO

A highly environmentally benign protocol for the synthesis of quinazolinones from anthranilamides and aldehydes via aerobic oxidation was developed in wet DMSO. This protocol is operationally simple, exhibits broad substrate scope, and does not need toxic metal catalysts and bases. In addition, the utility of this transformation was further demonstrated by converting the resulting quinazolinones into other useful products in the same-pot without their isolation.

Iron-catalyzed one-pot 2,3-diarylquinazolinone formation from 2-nitrobenzamides and alcohols

A novel approach for the synthesis of 2,3-diarylquinazolinones using iron as catalyst is described. Various 2-nitro-N-arylbenzamides reacted with benzylic alcohols to selectively give the corresponding products in the absence of external oxidant or reduct

One-pot three-component synthesis of 4(3 H)-quinazolinones from benzyl halides, isatoic anhydride, and primary amines

A novel, one-pot, and three-component synthesis of 4(3H)-quinazolinones is described. Benzyl halides are oxidized to aldehydes under mild Kornblum conditions then undergo a three-component reaction with isatoic anhydride and primary amines to produce 4(3H)-quinazolinones in excellent yields. Georg Thieme Verlag Stuttgart. New York.

A practical and versatile approach toward a one-pot synthesis of 2,3-disubstituted 4(3H)-quinazolinones

An effective one-pot three-component route to 4(3H)-quinazolinones from commercially available starting materials is reported. Thus, isatoic anhydride reacted with ammonium acetate or primary amines and aldehydes in the presence of iodine to produce the corresponding quinazolinone derivatives in moderate to good yields. Springer-Verlag 2010.